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The main characters of Crazy Ex-Girlfriend.

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    Rebecca Bunch 

Rebecca Nora Bunch

Played by: Rachel Bloom, Ava Acres, Kerrigan Milker (young)

https://static.tvtropes.org/pmwiki/pub/images/rachelbloom.jpg
To be clear,
I didn't move here for Josh, I just needed a change,
Cause to move here for Josh, now that’d be strange,
But don't get me wrong, if he asks for a date,
I would totally be like, "That sounds great."
Did it sound cool when I said, "That sounds great?"
Okay, how about now: "That sounds great."

Rebecca was a hard-working, driven young lawyer working in New York City when she happened to run into Josh Chan, her ex-boyfriend from summer camp ten years ago. Seeing him reminded her of just how happy she was back then (and how in love she was with Josh), so she quit her job and moved to West Covina, where Josh lived. But she didn't move there for Josh, nope.

Tropes:

  • Abusive Parents: Rebecca's mother is extremely controlling of her and blames her for her father walking out on them.
  • Adorkable: Her younger self. Her older self is generally too much of an emotional wreck to qualify, but it still occasionally shines through.
  • Aesop Amnesia: On multiple occasions Rebecca realizes what a fool she's been and tries to let go of Josh. Unfortunately, this rarely lasts for more than a couple episodes before she reverts to her old ways.
  • Affectionate Nickname: "Cookie" to Paula, "Becks" to Josh.
  • Always Someone Better: Consistently outperformed Audra Levine throughout their lives. Audra only achieved her high-powered junior executive position at her firm because Rebecca opted out of it to travel to West Covina.
  • Ambiguous Disorder: Rebecca in particular has serious problems with dealing with other people as brought up by herself and everyone in the show. Actually subverted — while the show has literally stated that some of her issues remain undiagnosed, it is very clear about her anxiety and depression, and she gets a more accurate diagnosis in season 3 (borderline personality disorder).
    Darryl's ex-wife: What the hell is wrong with you?!
    Rebecca: Off the top of my head? I'd say low self-esteem, a lack of maternal affection and a genetic predisposition for anxiety and depression.
  • Ambiguously Bi: Parodied with the song 'Feeling Kinda Naughty', where Rebecca isn't quite sure whether she has a crush on Valencia or is just insanely jealous of her. She even tries to kiss her! This is acknowledged when she talks with Darryl's ex wife in season 3, in which she says though she isn't bi, she does has bi tendencies and puts herself in a 1.8 in the Kinsey Scale (which would be technically bisexuality).
  • Angsty Surviving Twin: Played for laughs. Rebecca squicks out Paula by casually mentioning that one of the reasons she doesn't have much of a family is that she ate her twin in the womb.
    Paula: You ate your twin?
    Rebecca: I mean, medically speaking, I didn't "eat" it, I just metabolized its body parts for my own use.
  • Affably Evil: One way to look at her character, especially if you do it objectively. She's an intelligent, friendly, charming lady who genuinely cares for her friends and will usually try to help you out, who just so happens to be a crazy, clingy, ruthless stalker.
  • Arbitrarily Large Bank Account: Subverted. She spends massive sums of money at least Once an Episode throughout most of the first season, seemingly without any sort of financial trouble, until she eventually comes to the realization that all of her big spending has left her broke. This leads to a small scale Continuity Cavalcade as every time she spent a large amount of money earlier in the season is brought up.
  • The Atoner: Part of her arc in season four. She initially accepts going to prison for her crimes but later recognizes it as performative and starts genuinely working on herself and making amends.
  • "Basic Instinct" Legs-Crossing Parody: She's the page image.
  • Belligerent Sexual Tension: With Nathaniel in late season 3. An entire song is dedicated to it.
  • Betty and Veronica: Played with. Rebecca clearly sees herself as the Betty figure, being the more "plainly pretty" "girl next door" type, and utterly intimidated by the striking and icy Valencia. But from Valencia's perspective, Rebecca is a high-powered, Ivy League-educated lawyer from New York who came sweeping into their small town to manipulate her boyfriend away from her, which sounds a lot more like the Veronica figure.
    • Somewhat acknowledged, when Paula can’t decide which one of them is the “Taylor Swift” and which is the “Katy Perry” in their feud over Josh.
  • Big Eater: She likes to eat and makes no bones about it, frequently mentioning her love of donuts and bagles.
  • Bitch in Sheep's Clothing: Rebecca is generally nice and pleasant, but she is also extremely manipulative. She has a Heel Realization late in the first season when she realizes her status as this.
    • This is a bit of a subversion: she actually is a pretty nice person who just happens to have a very dark side, as well as an entire infernal horde of inner demons.
  • Black and White Insanity: She doesn't seem to handle gray areas well — part of what makes the Josh situation so awful is that she doesn't seem to get that neither she nor Josh is really 100% right or wrong here.
  • Brainy Brunette: Rebecca is a brunette with considerable intelligence.
  • Broken Ace: Rebecca is a great lawyer, a graduate of Harvard and Yale, and knows Mandarin. She was going to be made partner in her old, prestigious law firm. However, inside, she is a mass of self-doubt, self-hate, anxiety, and depression. When she screws things up with Josh, she ends up singing the song "You Stupid Bitch" to herself, even saying that she's done this a lot.note 
  • Bunny-Ears Lawyer: At least half-literally: Even in New York, she had made partner before she decided to move to West Covina; in West Covina, what little we do see of her actually working shows that her knowledge of real estate law is unparalleled. However, the show is mostly about her outside of work, and occasionally how her personal issues steamroll very quickly into her work.
  • Buxom Is Better: Several people have commented on Rebecca's large bust, even Valencia has complimented Rebecca on her appearance. Defied with the song 'Heavy Boobs' where Rebecca deconstructs this trope.
  • Byronic Hero: Despite being a deeply flawed human being she is still for the most part a kindhearted person.
  • Character Development: In some ways, the entire point of the show. Rebecca in season one has wild mood swings between serious depression and manic cheerfulness, which are part of what make her such an engaging character, but as she show goes on she is revealed to have serious mental health issues. Over the course of seasons two and three, she comes to accept this about herself. By season four, she's handling things in a much healthier way. Very realistically, she still goes into emotional tailspins and makes terrible decisions, but she recognizes this and deals with it much more quickly than she did in the beginning.
  • Cheerful Child: Flashbacks show that she was this until she started to get the impression that nobody loved her. Even when puberty hands her massive frizzy hair, a dental retainer and acne:
    Silas Bunch: What happened to your hair?
    Young Rebecca: Oh, certain hormonal changes have occurred. It's unfortunate, but such is life.
  • Color Motif:
    • Blue. She often wears blue in her musical numbers ("West Covina", "Let's Generalize About Men"), or has some sort of blue color around her ("You Stupid Bitch", "The End of the Movie"). She is introduced wearing a blue dress with a black blazer. Blue is a color often associated with deep sadness, which is what she is feeling most of the time and mirrors her unhappiness with her life.
    • In early season 3, she invokes this and decides to go in Light Is Not Good direction by dressing in white and painting her hair black, making her new color scheme focus on white, with some splashes of black, though she soon drops this and goes back to her more usual blue-scheme.
      Rebecca: My hair is dark, because I'm evil, but I'm wearing white, because it's ironic.
  • D-Cup Distress: The theme of "Heavy Boobs." Her large bust causes her all kinds of problems.
  • Deadpan Snarker:
    Dream Ghost Dr. Akopian: What were your other relationships like after that?
    Rebecca: With other men? Oh, my god, they were fantastic. They were beautiful, filled with respect and mutual orgasms. [withering stare] What do you think? They were disasters.
  • Desperately Craves Affection: Rebecca is desperate for affection and love and will cling intensely to anyone who shows her either, regardless of what she has to do to get it.
  • Disappeared Dad: Rebecca's dad left them when she was a teenager. She still tries to have a relationship with him, even though he's a complete deadbeat. She finally tells him to fuck off in the season two finale.
  • Ditzy Genius: Despite being an Ivy League graduate and a genius lawyer, Rebecca tends to make hasty, careless and downright idiotic decisions in her day to day life.
  • Driven to Suicide:
    • In season 2 finale, she has a breakdown following Josh leaving her at the altar, which leads her to run away to a cliff with the intent to run. Fortunately, Paula manages to talk her down from it.
    • She eats a whole bottle of anti-anxiety meds with the purpose to commit suicide. Last minute, though, she asks for the help of a flight attendant and they manage to get her to a hospital.
  • Dude Magnet: Josh, Greg, Nathaniel, Trent, several minor characters, possibly Heather... Rebecca gets a lot of romantic and sexual attention. (It's all but stated that she's quite promiscuous when she's single, too, and has no issues finding partners.) However, her craziness or outside forces often drive them off. (Except Trent, much to her dismay.) Occasionally lampshaded by guys observing her odd behavior.
    Hector: Dude, why are all my friends in love with this girl?
  • Expository Hair Style Change:
    • While in New York, Rebecca's hair was straight and perfectly groomed. When she settles into West Covina, she wears it in its natural curls, showing how much happier and more open she is in her new life.
    • In season three, she dyes her hair a much darker shade of brown after Josh leaves her at the altar.
  • The Fake Cutie: Likes to portray herself as a bubbly Ingenue, but, while genuinely a pretty nice person, she is in actuality far more savvy, manipulative and vindictive than she lets on.
  • False Friend: Becomes Valencia's best friend for a period of time in order to become closer to Josh. Rebecca herself denies it throughout the episode that it happens in, only to finally acknowledge it in the end, completely destroying her relationship with Valencia in the process. Subverted, as they do become genuine friends later on.
  • Fatal Flaw: Impulsiveness and a desire to push the responsibility for her happiness towards someone else. Rebecca's hunt for happiness takes precedence over anything else in her life, which ends up meaning put everything else on hold to chase someone, because she desperately for someone else to be responsible to make her happy, satisfied and give her self-esteem. This is what turns her into a romantic chasing after men while avoiding her actual issues.
  • Fish out of Water: She's a born and bred New Yorker who moves to a much smaller city in Southern California.
  • Freudian Excuse: She grew up with an emotionally abusive mother who relentlessly insulted and criticized her and a father who abandoned her and has made it clear he doesn't care very much about her. Unsurprisingly, this left Rebecca desperate for any kind of affection or love and willing to do anything to achieve it.
  • Freudian Excuse Is No Excuse: After Nathaniel (in song form) argues that both of them were messed up by their childhoods, and therefore nothing is their fault, Rebecca realizes that she needs to stop using that excuse and take responsibility for her own actions.
  • Genki Girl: Rebecca is the grown up version of this; she tends to start things out innocently enough but tends to take things way too far.
  • Glorified Sperm Donor: Rare Female Example. Rebecca is the egg donor for Darryl's new baby, but she doesn't carry the baby (Heather does) and barely interacts with Hebecca (yes, really) after the birth. Justified, since she chose to donate the egg at a low point in her life and associates Hebecca with that. She gets a bit better in "I Can Work With You" when she babysits.
  • Guy-on-Guy Is Hot: She certainly thinks so, as one of the many distractions she gets sucked into during "Time to Seize the Day" is masturbating to gay porn.
  • Heel Realization: Rebecca isn't necessarily a bad person but her actions can be very harmful to herself and others. She occasionally has moments of clarity where she realizes just how badly she hurts other people. This is explored in the song "I'm a Villain in My Own Story" where she comes to see herself as a Villain Protagonist.
  • Hello, Attorney!: When Rebecca's in court on TV because she's fighting the water case, and the others are watching, even Heather murmurs "I'd bang that gavel."
  • Hollywood Tone-Deaf: In the real world (as opposed to the show's fantasy musical numbers), Rebecca's singing is quite pitchy and bad, and much worse than Rebecca thinks it is.
  • Hope Bringer: Becomes this to Josh over time, as her unyielding love and belief in him fills him with feelings of confidence in himself for the first time in his life. It leads to him entering a Heroic BSoD after she tries to move on from him.
  • I Call Him "Mr. Happy": She's named her breasts "Bonnie" and "Clyde," and her ovaries "Hustle" and "Flow."
  • Improbable Age: While it's not impossible for a person to be offered the position of junior partner at a high profile New York law firm in their mid-twenties, it is certainly uncommon. This is one of the earliest indicators of Rebecca's exceptional intelligence, as well as her excessive devotion to things that interest her.
  • Irrational Hatred: Rebecca is pretty clearly shown to possess a thinly-veiled disgust of White Josh for no clear reason. In particular, she mentions that she finds his shirtless physique disgusting and compares his face to a chipmunk. This is especially confusing given that one of White Josh's defining character traits is his uncanny resemblance to Josh, the person who Rebecca is obsessed with.
  • It's All About Me: Rebecca is very impulsive and will do almost anything to be with Josh, without taking into consideration how others might feel about her behavior.
  • Ivy League for Everyone: Rebecca graduated from Harvard and Yale. Justified, in that she's repeatedly shown to be both incredibly hard-working (when she's motivated to be) and prodigiously gifted as a lawyer.
  • Jewish American Princess: She has the upbringing of one, at least. She even gets involved in a "JAP battle" with her lifelong rival and fellow Jewish American Princess.
  • Jewish and Nerdy: A gifted lawyer with an Ivy League pedigree as well as Jewish heritage.
  • Loving a Shadow: Much of her feelings for Josh can best be described as this, as he was the symbol of a happier and more carefree time in her life and she projects that desire onto him in the hopes that getting back with him will fix her problems. Naturally, it doesn't work that way and Rebecca learns that she has to address the real sources of her unhappiness and stop seeing Josh as a solution, especially because he has a large number of flaws himself.
  • Ms. Fanservice: The concept of Fanservice in general is parodied by her several times during musical numbers, which show her in provocative outfits only to juxtapose it with something decidedly unsexy, such as having to be helped on with a pair of Spanx.
  • Never My Fault: In an odd combo of this and It's All My Fault, Rebecca seems to swing back and forth between believing everything is her fault, and that nothing is.
  • Nice Guy: Subverted. Rebecca would like to believe she is one, and she is incredibly friendly, helpful and supportive to people she likes. She genuinely always wants to do the right thing, even when her actions don't match up. On the occasions when she realizes just how harmful she can be to others, she lapses into a Heroic BSoD. However, she's too manipulative and too much of a Stepford Smiler to be a truly straight example.
  • Normal Fish in a Tiny Pond: She was already a pretty big fish in New York, where she was offered a junior partner position at a prestigious law firm in her mid-twenties, with her employers showing a willingness to out-bid competitors to keep her under them. In West Covina, though, she's unquestionably the best lawyer in town. Even her boss hires her to represent him in his custody case. And she's in real estate.
  • Psycho Ex-Girlfriend: Implied from the title, but ultimately subverted. Rebecca may be pretty fixated on Josh, but her problems with needing to be liked go back much further. If it wasn't Josh, it would have been something else.
  • Sanity Slippage: Starting mid-season two and especially season three, Rebecca's grip of reality and common sense is slowly but surely going out the window. Not that she was ever a pinnacle of sanity to begin with, mind you.
  • Screw the Rules, I Have Money!: When told that no matter how much she donates to Josh's camp program, she will never get a position as a camp counselor, Rebecca writes a cheque and hands it to the camp director, who stares at it wide-eyed for a moment and then says "This'll do. Welcome aboard."
    • Downplayed in later seasons because she stops being a lawyer and starts running her own business selling pretzels. By season four she's resigned to not having much money anymore, but also has learned not to impulsively spend money she doesn't have and ratchet up debt.
  • Selective Obliviousness: This is how Rebecca's Ambiguous Disorder most prominently manifests. She constantly denies that she moved to West Covina to date Josh or that she even wants to date Josh, before running across town to "spontaneously" bump into him at a location he checked into on Facebook.
  • She's All Grown Up: She's shown to have been awkward and dorky as a teenager, whereas she's more or less universally seen as beautiful as an adult. This only applies to looks, however, as she still has a lot of mental growth left to do.
  • Soap Box Sadie: She's prone to lecturing people on the latest progressive ethics, and once wondered why the Hispanic chefs at a Mexican restaurant weren't more insulted by the menu not being authentically Mexican enough. She's not necessarily portrayed as wrong most of the time, but people don't usually listen to her - and of course it doesn't help that she's rarely able to practice what she preaches.
  • Stalker with a Crush: She is this, despite her insistence that she isn't one for Josh Chan. She's not above knowing where Josh is at all times and following him for her own ends.
  • Stepford Smiler: She's quite energetic and friendly which covers up the fact that she suffers from some very serious issues.
  • Straw Feminist: Downplayed, as self-proclaimed feminist Rebecca is the hero of the show and usually framed as having valid points. However, there are satirical moments when she throws around feminist buzzwords for clearly disingenuous reasons, like when she accuses her therapist of 'mansplaining' when he diagnoses her with BPD.
  • "The Reason You Suck" Speech: Has been on the receiving end of this from several characters who get fed up with her antics. Including an epic one from herself.
  • Took a Level in Jerkass: Season 2 generally portrays her as being much more self-absorbed, abrasive and whiny than she was in season 1. Justified, as it's suggested that she's always been like this and the audience is only now seeing it as a result of the Protagonist-Centered Morality that surrounded season 1 starting to slip away.note 
  • Trademark Favorite Food: Pretzels, though less because of the food itself and more because they're a symbol of her happiness in West Covina, which two pretzels lampshade in this song.
  • Ultimate Job Security: Played with. Rebecca does a lot of extreme things that would likely face repercussions in real life, such as skipping work on a whim or acting inappropriately at meetings, but continues to stay on at the firm. However, when she is serious about her work, she's a brilliant lawyer who gets things done. Part of this is because her background makes her one of the best lawyers working in West Covina despite her issues. Working with a boss like Darryl also helps.
    • Finally subverted in Season 4. Even though the charges ended up getting dropped, the fact that she was sent to jail means that it's up to the bar association whether or not she gets to continue practicing law.
  • Unsympathetic Comedy Protagonist: Deconstructed with extreme precision. Much of the show is from Rebecca's POV, so she sees herself as the romantic heroine who just wants to find love, and to whom bad things happen because other people are mean to her. Increasingly, as the show goes on, she is shown to be her own worst enemy, not because she's a villain, or even all that unsympathetic, but because she has serious personal problems that regularly cause her to behave like an asshole towards the people around her. She is intermittently aware of this, but one of her problems is self-hatred, so she's a poor judge of when she's doing the right thing and when she isn't. Even when she is being nice, it's implied that she is doing so for the wrong reasons (see "Well Done, Daughter!" Girl).
  • The Vamp: While it's not her primary characteristic, Rebecca is very comfortable with trying to leverage her sexuality to get things done and is quick to try that tactic whenever more dignified methods fails - Rachel Bloom has stated in so many words that Rebecca associates sex with power. Parodied in that she's always extremely unsubtle in her flirting, compared to the artful way most versions of this trope go about it - in a sense, she's an Unskilled, but Strong Vamp.
  • Villain Protagonist: By season three, she's definitely this. While she's still sympathetic, engaging, and likable, it's clear that she's not the good guy here, and that Josh was perfectly justified in leaving her. The song "After Everything You Made Me Do" seems designed to highlight this. Once you hear all of Rebecca's misdeeds up until that point listed out, one after the other, it becomes a lot harder to deny the fact that she's a manipulative, petty, crazy stalker.
    • Averted in season four, where she's accepted that she needs to take responsibility for her own bad actions and, also, that she's got borderline personality disorder, and shouldn't excessively blame herself for things that aren't her fault. She becomes a much more stable and less manipulative person.
  • Weight Woe: She is self-conscious about her weight, to the point of calling herself "fatty" whenever she falls into one of her bouts of self-pity. This is suggested to be the result of her mother's overly-critical parenting style.
  • "Well Done, Daughter!" Girl:
    • Rebecca always tries to impress her mom. Paula calls her a "level-5 mom pleaser".
    • As bad as her relationship with her mom is, her relationship with her father is even worse. While Rebecca recognizes how awful her mother is, she still adores her dad even after he abandoned her. It takes until the end of Season 2 for her to see him for the neglectful, selfish deadbeat he is.
  • Womanchild: It's implied that Rebecca hasn't matured much past her teen years.
  • Wrong Genre Savvy: She sees herself as the heroine of a romantic comedy, where Josh is the love interest and they're (eventually) going to live happily ever after. She's unfortunately in a deconstruction of one, so her efforts never pay off the way she wants them to.
  • Your Cheating Heart: Despite being engaged to Josh, she kisses Nathaniel in season 2 episode 11.

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    Josh Chan 

Joshua "Josh" Felix Chan

Played by: Vincent Rodriguez III

https://static.tvtropes.org/pmwiki/pub/images/joshchan.jpg
But recently someone said something to me, I don't want to say who...Greg. On one level, I didn't think it was true, but on another level, it is true. So there are, like, two things going on in my brain right now.

Josh Chan was Rebecca's summer camp boyfriend back in 2005, but broke up with her on the last day of camp because she was "dramatic and weird." Ten years later, he is moving back to West Covina from New York when he ran into Rebecca again. It turns out that he has a small circle of friends in West Covina (including Greg, Hector, and White Josh) and a long-term girlfriend (Valencia).

He's also not the brightest person, described by the creators of the show as an "Asian bro."

Tropes:

  • Ambiguous Disorder: Rebecca comments that he might "be on the spectrum" and in season 2 we find out that he suffers from intrusive thoughts, as sung about in Thought Bubbles.
    • Josh shows a large number of traits of Narcissistic Personality Disorder as well, including exaggerating his own importance, requiring constant attention and admiration from others, and expecting an unreasonable amount of special treatment.
    • Josh actually starts worrying about this in Season 4. At first he turns to online clickbait quizzes to diagnose himself, but Heather and Hector manage to persuade him to see an actual therapist instead. While he definitely has some issues to work through, it doesn't seem as if he has a disorder after all.
  • The Artifact: His plot relevance in the back half of season 3 is greatly reduced, with Nathaniel assuming the post of Rebecca's Love Interest and Josh being more of a Comic Relief, only loosely related to other character's stories. He regains prominence in season 4.
  • Asian Airhead: A rare male example of this (and inversion of Asian and Nerdy). He's not an idiot, but he tends to be slow on the uptake.
  • Berserk Button: Josh is normally extremely mellow, even scared of conflict. Threaten his family, though, and that changes in a hurry.
  • Betty and Veronica:
    • Zig-Zagged. He is the "prize" that Rebecca is attempting to be with, making him a Veronica. However, Josh is also far more good-natured, open and friendly with her on a surface level than Greg is, giving him the qualities of a Betty. However, Josh tends to make every situation he's in revolve around himself, shows serious signs of narcissistic personality disorder, and is in-general a rather terrible boyfriend, which pushes him back into Veronica territory.
    • In the second half of season 2, Josh is a more straightforward Betty (friendly and engaged to be married to Rebecca) compared to Nathaniel's antagonistic, cold, high-status Veronica.
  • Bitch in Sheep's Clothing: An extremely interesting example. Every single one of Josh's Nice Guy tendencies is 100% genuine. He really is that friendly and positive and is genuinely not mean-spirited at all. However, Josh's narcissistic tendencies, Manchild behavior, and Commitment Issues make any relationship with Josh that goes past the surface level extremely unpleasant and leads to an incredibly large amount of Jerkass behavior from Josh towards those around him.
  • Brainless Beauty: Downplayed. He's good looking but is also pretty oblivious and naive about most things outside of his comfort zone.
  • Broken Ace: Handsome, popular and genuinely friendly, but also believes himself to be unprepared for adult life and has surprisingly low self-esteem as a result.
  • Character Development: After Josh goes into therapy, he's still inclined to be insufferably self-absorbed, but he becomes much more acute about other people's issues, and completely nails why Paula is scared to study for her exams.
  • Chick Magnet: He's been popular with women since high school, and is considered the ladies' man of his friend group. He's able to remain in denial about how serious Rebecca's feelings are for him because, in his words, "most chicks I know are a little into me."
  • Childhood Friends: He and Greg have known each other since they were five.
  • Childhood Friend Romance: He and Valencia have been dating since they were eleven, and have likely known each other for even longer than that.
  • Commitment Issues:
    • Josh is reluctant to settle down with any woman he dates, often coming up with excuses as to why it's their fault and not his fault. With Valencia, who he dated for fifteen years, he blamed her for being overly-controlling and cited his unresolved feelings for Rebecca (which didn't start until the last few months of their fifteen year relationship). With Rebecca, he cited her personal, mental, and emotional issues as well as a sudden calling to become a priest.
    • Additionally, Josh quickly abandoned the lifelong commitment to become a priest as well when just how serious the commitment was became clear to him.
  • Dumb Jock: Josh isn't very smart, but he is incredibly athletic, has several black belts, and is a very good dancer.
  • Fatal Flaw: Immaturity. Josh is a Manchild pushed into adulthood by everyone around him. He dislikes commitments, responsibilities, not being the center of attention and hates the fact that things are changing around him. He is specially weak to his own guilt, and rather than making up for what he has done, he only wants to relieve himself from that guilt in the easiest way possible, these all combine in why he left Rebecca at the altar (he didn't wanted to commit, didn't liked to work in the wedding and ran away to be a priest, because he believed that then all of his problems would be solved by themselves and holy forgiveness would relief him).
  • Firemen Are Hot: Partway through Season 3, he finds a new job that he describes as something along the lines of a volunteer firefighter. He's really a dancer at a gay bar that wears a fireman outfit.
  • Full-Name Basis: Because his name is so simplistic and he hangs out with a guy called "White Josh," he gets called "Josh Chan" a lot.
  • Future Loser: Downplayed. He is suggested to have been the Big Man on Campus during high school, and while he's still generally popular and happy in the present, he does not appear to have any real plans for his future and is content with keeping his life as close to how it was in high school as possible.
  • Green-Eyed Epiphany: Late in season 1, he starts having complex feelings towards Rebecca after learning that she and Greg are an item. This is not helped by Valencia pressuring him to propose to her.
  • Hates Being Alone: The season 2 song "Thought Bubbles" is about how Josh finds it very difficult to be alone with his thoughts, which explains why he is so sociable and outgoing but which also implies that he's not nearly as happy and content as he (and everyone else) likes to think he is.
  • Henpecked Husband: Played With. Early on, he appears to be a non-married example towards Valencia. She has an iron grip on his friendships and controls almost everything he does. Later on as it reveals that he has inadvertently been the one straining their relationship due to his refusal to take the next step in their relationship.
  • Hope Bringer:
    • Regardless of how their relationship is interpreted, Josh's reappearance in Rebecca's life is what caused her to abandon her career in pursuit of genuine happiness, and his presence serves as a constant source of inspiration for her not to give up.
    • Subverted towards the end of Season 2 and Season 3, where Josh's role in Rebecca's life and his treatment of her is the final straw to pushing her on a downward spiral.
  • Ignored Epiphany: Played with. When it's pointed out that he uses women to flee away from trouble and guilt in his life, he genuinely takes it to heart. Unfortunately, he doesn't really understand that the issue is the fact that he's running away from his problems, rather than the specific method he chooses. As such, while he does resist the temptation to use the girl he just met as a distraction in the Season 2 finale, he instead decides to go join the priesthood.
  • It's All About Me: As said above, Josh shows several signs of narcissistic personality disorder. While he's not exactly domineering, he generally expects to being the center of attention. He often blames his problems on other people, refuses to take responsibility for his mistakes, and is almost solely focused on his own feelings, while not registering those of others. After he leaves Rebecca at the alter and she angrily rants about all the insane things she's done to be with him, his immediate reaction is relief, because he doesn't have to feel guilty about leaving her. Taken Up to Eleven by the Season 3 midseason finale, where Josh takes Rebecca's suicide attempt and still warps it into being all about him. He's frequently called out on this behavior, and he does finally seem to be getting it.
  • In Love with Love: Downplayed, but in season 4, Rebecca correctly realizes that his feelings for her are more because he's now ready to be in a serious relationship.
  • Jerkass: Unintentionally so on his part, but very much still an example. Josh tends to be self-absorbed, petty, and immature in any and all situations, leading him to be extremely unpleasant in a large amount of situations (particularly if they're about someone else and not him).
  • Kick the Dog: His leaving Rebecca literally hours before their wedding to become a priest and leading her to almost commit suicide comes across as a truly epic example of this.
  • Last-Name Basis: Is called "Chan" semi-regularly, likely due to being close friends with another Josh.
  • Lovable Jock: He is genuinely friendly, happy and unassuming most of the time, and it takes a lot to shake his resolve.
  • Manchild: Josh has had a hard time growing up and getting a job. Additionally, his approach to relationships tends to be extremely childish and immature.
  • A Man Is Always Eager: When he was in a bad mood, he turned down Valencia's advances. He genuinely didn't even know it was possible for a man to turn down sex.
  • Mr. Fanservice: Due to Rebecca's obsession with him, his good looks are talked about constantly. After his chiseled physique is steadily hyped up throughout the first season, he is finally given an extended Shirtless Scene during the finale.
  • Nice Guy: Even though Josh is handsome and popular, he's also shown to be nice and friendly to pretty much everyone. His ability to consistently treat Rebecca nicely and as a friend is what causes her to continue to obsess over him.
  • Oblivious to Love: The dude simply cannot understand Rebecca's feelings. After finding out Rebecca is moving back to New York immediately after he decides he can't be with her, he's still wondering "why would she leave?"
  • Odd Friendship: He and Greg couldn't be any more different from each other, but have remained strong friends for over two decades.
  • O.O.C. Is Serious Business: Whenever he's not cheerful and happy, it's a sign something is wrong. This is commented on In-Universe.
  • On the Rebound: Hooks up with Rebecca and starts having a relationship with her (she thinks it's serious, very clearly; he considers it to be casual sex and it gives him a place to live) less than an hour after breaking-up with his girlfriend of fifteen years Valencia.
  • The Pollyanna: He's usually happy. Darryl even calls him "the happy man" and considers it particularly worrisome if Josh isn't happy.
  • Sexy Priest: Left Rebecca at the altar to enter a seminary at the very end of Season 2. It doesn't take long for him to get bored with the process, and Rebecca showing up and spilling her crazy is all the excuse he needs to quit.
  • Turn to Religion: Goes through a bout of this after realising that he doesn't want to marry Rebecca after all and leaving her at the altar. While religion had always been important to him, he was inspired by the certainty felt by a priest friend of his and believed that if he joined the priesthood, too, he'd know what he was meant to do in life. However, even early on his friend suspected he was just using the priesthood as a way to run away from his problems, something quickly proven (and through a rather snazzy musical number to boot) once he joins up and realises it requires a lot of quiet studying he was not at all prepared for. After a few episodes, he quits.
  • What Is This Feeling?: After seeing Rebecca with Greg, he gets really angry and since he's The Pollyanna, he has no idea why or even what he's feeling. It would be Is This What Anger Feels Like? but the concept is so foreign to him that he doesn't even know it's anger.

    Paula Proctor 

Paula Proctor

Played by: Donna Lynn Champlin

https://static.tvtropes.org/pmwiki/pub/images/paulaproctor.jpg
I perioded on an ultra suede settee in 1987 at Roberta Janatelli's condo and I gotta tell you it was still a great party. I wrapped a sweater around my waist, then hooked up with Bobby Henderson anyway! And I started the whole sweater-around-the-waist trend! So, you're welcome.

Paula Proctor is the head paralegal at Whitefeather and Associates, the law firm that Rebecca joins when she moves to West Covina. Paula is instantly suspicious of Rebecca's motives for moving there and quickly figures out that it was due to Josh Chan, but instead of revealing this, she becomes Rebecca's friend and confidant, helping her in her schemes to get closer to Josh.

She is married with two children, although her marriage is on the rocks.

Tropes:

  • Adult Fear: As soon as Rebecca reveals to have lost her son in a club, she automatically gets serious while questioning her whether anyone gave him drugs or abused him. After it's confirmed that he just got lost and then came back home, she feels fully relieved, admitting that her son gets lost all the time and she is used to it, but she was afraid of what could have happened to him in a club.
  • Alliterative Name: Paula Proctor. The catchiness of her name is lampshaded a couple of times, with her husband noting that it's a great name for a lawyer.
  • Awful Wedded Life: Zig-zagged. At first, there are numerous problems with Paula and Scott's marriage (apparently, she hasn't had sex without the TV on for ten years). It starts to get better when they go to marriage counseling, and bond over throwing a rock through Rebecca's window. By Season 2's "When Will Josh and his Friend Leave Me Alone?", Paula and Scott's marriage is positively heartwarming. Then in "Who is Josh's Soup Fairy?" he confesses to having had sex with Tanya, and Paula immediately boots him out of the house. They go back to marriage counseling and are back to being Happily Married by the end of "Josh's Ex-Girlfriend Wants Revenge."
  • Beleaguered Assistant: To Darryl and the other lawyers in the office. Rebecca accidentally mistakes her for her new secretary; Paula has to point out that she's head paralegal, which is very different.
  • Berserk Button: Infidelity is a very sensitive issue for her. When Scott fesses up to having an impulsive one-night stand with a coworker, she immediately throws him out of the house without a second thought. Even when she finally relents and lets him start trying to win her trust back, she's downright draconian about the hoops he has to jump through.
  • Character Development: Paula goes from a woman crazy to get any sort of fun and escapism from her marriage to a woman who is a loving wife and mother over time, as she stopped dedicating so much to Rebecca's love life in later seasons. While her initial behavior was pushing Rebecca further over the edge, it's now of the most grounding things Rebecca has in he life.
  • The Confidant: Becomes the only person in West Covina who Rebecca is willing to confide her most personal feelings with by the end of the first episode.
  • Crusading Lawyer: Becoming a lawyer was always a dream of hers, and she starts law school in season 3. She also develops an interest in working cases for people who need representation, and catalyzes a new pro bono arm of the high-powered firm she works for in the end.
  • Deadpan Snarker: One of the mains sources of it, particularly towards her co-workers.
  • The Determinator: Played with. Paula is relentlessly driven when she decides she wants to do something, but that isn't always a good thing. Her dedication to Rebecca's love life is impressive, but also seriously ill-advised. When she decides she wants to be a lawyer, she devotes herself to it with equal fervor, but that often results in her alienating or neglecting the people around her. While studying for the bar exam, she becomes so focused that she tries to power through what turns out to be a heart attack... for 18 hours!
  • The Dog Bites Back: In "Josh and I are Good People", it's shown she is bullied in the office for being a paralegal rather than a lawyer. When Rebecca and Darryl leave to take care of a case, they let her run the office, and she takes the opportunity to pay back for every time Karen, Tim and Jim pissed her off, including threatening Tim with deportation after finding out he is illegally in America. She backs down thinking about his family, but none of them ever disrespected her again.
  • Fatal Flaw: A desperate desire to escape her unpleasant reality. She latches onto Rebecca's crazy love story as another hobby to distract her from the crazy and ungrateful life she leads with her family of a neglectful husband and two problem children, which leads her to become an increasingly toxic influence for Rebecca. She eventually drops this, however.
  • Fiery Redhead: She's a redhead and has a tendency to become extremely fired up when planning ways for Rebecca to become closer to Josh.
  • Heel–Face Turn: While never evil, she goes from antagonistic towards Rebecca to her best friend over the course of the first episode.
  • Hypercompetent Sidekick: Paula is extremely adept at gathering intel about Josh, as well as formulating strategies to get closer to him on the fly. Played with, in that she frequently does these things expressly against Rebecca's wishes.
  • Jerk with a Heart of Gold: She's rude, pushy, scheming, manipulative, conniving... and she genuinely loves Rebecca with all her heart.
  • Like a Son to Me: Blurts this out about Rebecca from time to time. Never having had a daughter of her own is a huge motivator for Paula to meddle in Rebecca's life.
  • The Nicknamer: Paula is this only with regard to Valencia, who at various times she has referred to as "Venezuela", "Valderrama", "Vaseline" and "Velveeta". Also refers to Rebecca occasionally as "Cookie".
  • Only Sane Employee: Her and Mrs. Hernandez, anyway.
  • Parents as People: While she dearly loves her children, Paula is quite neglectful and doesn't really enjoys spending time with them, not helped by the fact that her two children are quite awful people and dislike spending time with her too. As a result, she often ignores her family beyond the most basic of needs to latch on to her hobbies, which included vampire novels and later, Rebecca's love life.
  • Parental Substitute: While it's mostly the other way around, she eventually becomes a motherly figure for Rebecca, who even calls her "Mama" at least once.
  • Poisonous Friend: She'll do anything for Rebecca. Even when Rebecca expressly doesn't want her to do it. If she thinks it'll help Rebecca get closer to Josh, it'll get done.
  • Secret Chaser: Served as this towards Rebecca throughout the first episode, only for Rebecca to admit her intentions, causing Paula to instantly become her most loyal ally.
  • She Cleans Up Nicely: She's stunning when she slips into something other than her usual office-wear. Her red dress in "His Status is Preferred" is a particular standout for how sexy Paula can actually be. No wonder Calvin was interested!
  • Sitcom Arch-Nemesis Subverted. She's set up as this throughout almost all of the first episode, acting highly suspicious of her and snooping in on her personal life. By the end of the episode, she ends up becoming Rebecca's closest friend and confidant, as well as her sole ally in her pursuit of Josh.
  • Shipper on Deck: Massive shipper for Rebecca and Josh, she'll do anything to get them together.
  • Talking Down the Suicidal: She has to stop Rebecca from jumping off a cliff after Josh abandons her at the alter.
  • Undying Loyalty: Becomes even more devoted to getting Josh and Rebecca together than Rebecca herself is in a very short amount of time.
  • Vicariously Ambitious: She really wants to see Rebecca get together with Josh, in part because of her own romantic failings. In the pilot, she stated that she wished she were as brave as Rebecca, throwing everything away for love, so it's clear that at least part of the reason she is helping Rebecca is to live vicariously through her.
  • Well-Intentioned Extremist: She wants Rebecca to be happy, but, through a combination of her Wrong Genre Savvy idea about relationships, as well as her desire to vicariously live out her unfulfilled dreams through Rebecca, only succeeds in helping Rebecca's unhealthy fixation with Josh grow.
  • Wrong Genre Savvy: Like Rebecca, she sees their lives as a grand romance, with herself in the role of the sassy and supportive friend. This becomes a real problem, because she becomes seriously invested it Rebecca getting together with Josh, not only enabling Rebecca's bad behavior, but even pushing her to go to greater extremes. Eventually she realizes that she's trying to live out this story by proxy to escape her dissatisfaction with her own life, and gets better.
  • Your Cheating Heart: She almost cheats on her husband with Calvin. Rebecca intervenes and stops her from going through with it, and she and her husband go to counseling instead.

    Greg Serrano 

Greg Serrano

Played by: Santino Fontana (Seasons 1 & 2), Skylar Astin (Season 4)

https://static.tvtropes.org/pmwiki/pub/images/gregserrano.jpg
Hey, West Covina,
Why won’t you let me break free?
Am I doomed to stay here,
Pouring my high school friends beers,
For the rest of eternity?

Greg Serrano is Josh Chan's best friend since childhood. He works at the Home Base, a baseball-themed bar/restaurant that's right next to a baseball field, so it mainly gets drunks and eleven-year-olds. He's bitter about his mother leaving him when he was younger and longs to quit his job and go back to college, but still needs to earn money to pay for his dad's emphysema treatment.

He also has an unrequited crush on Rebecca, although he realizes that she's not a good person.

Tropes:

  • The Alcoholic: Greg works as a bartender and is frequently seen drinking. This is played as a personality quirk for most of the first season. In season 2, it's revealed that his drinking has caused much more severe problems than we'd realized, Greg admits that he has a problem, and decides to get sober.
  • Back for the Finale: Greg returns to the show for its fourth and final season, after previously having departed early in season 2.
  • Betty and Veronica: Played with. While he's the less-idealized more down-to-earth option that Rebecca could "settle for", he is also callous, antisocial and has severe Commitment Issues, making him a Betty with the qualities of a Veronica.
  • The Bus Came Back: Kind of. Greg cameos via butt dial in the season three episode "Josh's Ex Girlfriend Is Crazy." His father informs Rebecca that Greg is in a healthy relationship with a girl in his class at Emory, is still sober, and is the happiest he's ever been. He later officially returns for the final season.
  • Brilliant, but Lazy: Deconstructed. He's certainly smart, but his refusal to apply himself out of a combination of indifference and a fear of failing leads to him being much less intelligent and capable than he could be. This is illustrated very well in the song 'But I Could If I Wanted To'.
  • Character Development: Once Greg leaves West Covina, he manages to settle down with a girl, quit drinking altogether and seems to have put his life on tracks. His development ultimately serves as a major reason for him being played by a different actor in the final season.
  • Childhood Friends: Has known Josh since they were five.
  • Commitment Issues: Greg is afraid to fully commit because he fears having his heart broken.
  • The Cynic: Greg isn't what you'd call an optimist.
  • Deadpan Snarker: One of his main roles in the group dynamic.
  • Dogged Nice Guy: Pretty much a deconstruction - Greg likes Rebecca and tries to go on a date with her, but when goes home with someone else, he realizes that she's not a good person and has lots of problems, so he decides to stop trying. He still has feelings for her, but he tries to avoid them.
  • Drowning My Sorrows: Greg tends to use alcohol to mask his problems. In Season 2, he's forced to confront the fact that he's The Alcoholic, and he starts making a real effort to get sober.
  • Fatal Flaw: Self-sabotaging. Greg dislikes the idea of failure, so he never really applies himself, insisting that the poor results are because he doesn't care, rather than because he wasn't good enough. This is wholly illustrated in "But I Could If I Wanted Too", in which he insists that he could do whatever he wanted, but nothing matters enough to work hard on.
  • Green-Eyed Monster: Clearly harbors some resentment towards Josh for always being more popular and outgoing than he was throughout their lives, which is only magnified once Rebecca enters the picture.
  • I Want My Beloved to Be Happy: In the first season finale he disappoints Rebecca so she can seek happiness with Josh. Something of a deconstruction, showing there can be a thin line between this and plain old self-sabotage.
  • Informed Attractiveness: Played for laughs. Paula constantly raves about his good looks, and later episodes reveal that all middle aged women find him irresistible. To all other people, while he's noted to be a pretty good looking guy, he's never treated as remarkably handsome like Josh is.
  • Jerk with a Heart of Gold: Snarky, mean-spirited and apathetic, but also a genuinely caring guy who appreciates both his friends and family.
  • Missing Mom: Deconstructed with Greg's mom. Greg resented her for years, because he felt that she'd abandoned him. The reality is that Greg wanted to stay with his dad, and she tried to maintain a relationship with him, even when she remarried and started a new family. Greg blamed all his frustrations and jealous over the situation on his mother, even though she'd apparently done nothing wrong. Greg eventually realizes just how shitty he is treating his mom, and decides to be nicer to her.
  • The Nth Doctor: When Greg returns in the fourth (and final) season, he's played by a different actor. Aline Brosh McKenna & Rachel Bloom explained the change as Greg being "reimagined" after the conclusion of his original arc in season 2, reflecting on how your perception of people (and in this case, Rebecca's) can change over time.
  • Odd Friendship: He's a cynical asshole with a Hidden Heart of Gold while Josh is a kind-hearted Pollyanna. Despite this, they've been friends for most of their lives.
  • Only Sane Man: Greg often plays this role, commenting on the bizarre behavior of everyone around him, especially Rebecca. Of course, as the show goes on, it becomes clear that he's got his own problems.
  • Put on a Bus: In the fourth episode of season two, Greg tells Rebecca he loves her and then boards a plane to start school at Emory University.
  • Stepford Snarker: Greg is rather bitter about how his life has turned out and this shows in his sarcastic demeanor.
  • Small Town Boredom: Verging on Hated Hometown; Greg resents having to stay in West Covina and would like nothing more than to leave it and focus on his own life. He eventually gets his wish.
  • The Snark Knight: Greg feels like an unappreciated sane person who's doing uncharacteristically bad in a backwards town. It takes Heather of all people to make him realize his standards are way too high.
  • Tall, Dark, and Snarky: Has all the classic traits of this.

    Darryl Whitefeather 

Darryl Whitefeather

Played by: Pete Gardner

https://static.tvtropes.org/pmwiki/pub/images/darrylwhitefeather.jpg
‘Cause I love my daughter, but not in a creepy way,
Though I realize father/daughter love comes off that way.
I just love my daughter—but again, not in a creepy way.

Darryl Whitefeather is the head lawyer at Whitefeather and Associates. He is 1/8th Chippewa and asks to be called "Chief" by his employees (although nobody does it). He hires Rebecca after she moves to West Covina and is frankly astounded that anyone of her skill level would work there. He also asked her to represent him in his divorce case, because he was worried that his ex-wife would get full custody of his daughter.

Tropes:

  • Abusive Parents: While we haven't heard anything about his mom, in season 2 Darryl says his dad yelled at him a lot and called him an "emasculated sock puppet". Which he repressed for years.
  • Adorkable: Darryl is overly enthusiastic and eager to please and wears his heart on his sleeve. This adorkability is what attracts White Josh to him in the first place.
    Darryl: "That was funny (Whijo kissing him) is that a European thing or was it something Hector put you up to?"//
    White Josh: "No dude, I'm gay. You were being really cute so..."//
  • Age-Gap Romance: With White Josh. Darryl is somewhere in his forties and White Josh is 26.
  • Amicable Exes:
    • While he was initially on fairly bad terms with his ex-wife, Rebecca eventually succeeds in making them reconcile with each other.
    • Although he and White Josh are initially awkward around each other when they first break up, they soon realize that both of them want to stay friends. Darryl even pushes White Josh to go on dates with other guys.
  • Attention Whore: He desperately wants to be noticed and included.
  • Badass Mustache: White Josh says that it makes him look like Tom Selleck. Rebecca is shocked when he shaves it at the end of "I See You."
  • Benevolent Boss:
    • Although he can be a bit of a Bunny-Ears Lawyer, he is still a good boss to his employees, giving them "Weekend Tuesdays" and such.
    • Comically played with in his treatment of Maya, the new administrative assistant. In the staff meeting which he's called to announce that he's bisexual, he interrupts her attempt to introduce herself with "Maya, this is not the time! This is not about you, okay?". He later gets over his hatred of her in season 2, when he admits that he sees her as the embodiment of everything he hates about himself, finally making him a completely benevolent boss.
  • Beta Couple: He and White Josh are relatively stable, with the drama in their relationship being realistic and resolved through good communication. It's a point of contrast against Rebecca's extremely turbulent personal life. They break up in season three, however.
  • Bi the Way: Officially calls himself this as of "Josh and I Go to Los Angeles!". There's an entire song about it.
  • Bigger Is Better in Bed: Rebecca asks him if he's good in bed at the end of "I See You," and he informs her that his penis is huge.
  • Bumbling Dad: Subverted. Despite being a bumbler most of the time, he's actually a much better parent than his ex wife and is extremely attentive and affectionate towards his daughter.
  • Bunny-Ears Lawyer: An odd case. While he actually is a lawyer, and is very eccentric, there's no indication that these two qualities intersect at all. We don't get to see much actual legal work being done at the office, but when we do, we see him acting reasonably professional while Rebecca, who is much more concerned with her personal problems than her work, is the one making a scene.
  • Camp: He's extremely effeminate and flamboyant. Many of his employees assumed he was a closeted gay man before he came out as bisexual.
  • Celebrity Resemblance: According to White Josh, he looks like Tom Selleck.
  • Coming-Out Story: He has one in the second half of the first season.
  • Cool Loser: Darryl is usually portrayed as being a bit of a joke, yet he's the head of his own legal firm, a good parent, a forgiving and friendly ex-husband and has an incredibly strong relationship with a young, attractive and caring boyfriend. He's pretty much the only character anywhere near close to having his act together.
  • Fire-Forged Friends: Eventually, with Maya the administrative assistant.
  • Foil:
    • To every parent in the show. He is the sole Good Parent in the plot, and it shows, as Madison is shown to be intelligent and well-adjusted (if a little snarky) and is sometimes more down to earth and sane than her father. Even being the one that plots an encounter between him and White Josh that forces them to talk about his problems and break up.
    • He is also a major foil to Rebecca. They're both desperate for affection but Darryl doesn't lie and break the law like Rebecca does and when he gets into a relationship, it's one full of trust and honesty.
  • The Friend Nobody Likes: Desperately wants to be acknowledged by Rebecca and Paula as a close friend, and while they mostly seem to like him, they're also generally indifferent to his presence. This poor treatment is reflected in his treatment of Maya, who he admits to seeing a lot of himself in. They become genuine friends eventually.
  • Good Parents: He's an incredibly loving father who bursts into tears at the thought of losing custody of his daughter, and later dotes over his baby daughter Hebecca.
  • Has a Type: Inverted. He's proud of not having a type ("I don't even have a gender!"), and is actively hurt when his boyfriend turns out to have one which he fits, since he feels it makes their relationship less special.
  • The Heart: Possibly the sweetest person on the show. When Rebecca tells him off at the intervention in season 3, even Nathaniel is disgusted because hurting Darryl comes off as going too far.
  • I Just Want to Have Friends: Darryl has been rather lonely since his divorce. He's willing to do pretty much anything for the change to have friends.
  • Important Haircut: He shaves his mustache by the end of "I See You," and Rebecca even lampshades how crucial it was for his image.
  • Meet Cute: When he first meets White Josh, the first thing Whi Jo does is take his shirt off and welcome him.
  • My Biological Clock Is Ticking: Manages to act out this trope practically to the letter despite being 1) male, 2) middle-aged, 3) already a parent. Once he gets the idea into his head of having another child, he gets so excited about it that he can't stand to wait another second, causing him to act very much like a woman who feels like time is running out - even breaking up with his boyfriend when it turns out he doesn't want kids and opting for single parenthood instead.
  • Nice Guy:
    • Boundlessly optimistic and nice. (Except to Maya the administrative assistant. And even then he ends up admitting to her that he's being a dick to her because she reminds him of everything he doesn't like about himself. After that they become strong friends.)
    • Exaggerated in "I See You", in that Darryl constantly wanting to talk to Rebecca about her feelings drives her completely up the wall.
  • No Bisexuals: Discussed and defied in his solo number "Getting Bi", where he acknowledges the common belief that all bisexual men are simply gay and in denial about it, only to firmly reject it as being untrue.
  • One Drop Rule: He clearly believes in (a positive version of) this, being very proud of being one-eighth Chippewa even though he clearly has no connections to the culture and all his American-Indian decorations are gaudy junk he got from a flea market. Season 3 reveals that his last name wasn't even originally "Whitefeather," but that he had it legally changed when finding out about his Chippewa great-grandparent.
  • Papa Wolf: When he hears about Rebecca's suicide attempt in season 3 he threatens to kill Josh. And when he gets a call from White Josh, who is babysitting his daughter Hebecca, in season 4, he goes from ranting about his bad night to screaming "What's wrong with my daughter?"
  • Parental Incest: Subverted but played for laughs. He deeply loves his daughter and isn't shy about saying it, but is very prone to moments of That Came Out Wrong that cause him to sound as if he is attracted to her.
  • Parental Substitute: He takes Nathaniel under his wing pretty soon after his arrival at the firm, and is one of the only people who can make him relax.
  • Plucky Comic Relief: While Darryl has his own problems, and the rest of the cast are all funny in their own ways, his conflicts tend to be resolved fairly easily, and he is otherwise around mostly as a source of humor.
  • Pointy-Haired Boss: He runs the office... interestingly. He once called a meeting just to announce to his staff that he was bisexual. He started an event called Weekend Tuesdays where everyone puts on fun hats and drinks on a Tuesday, although he doesn't seem to have thought the endeavor through:
    Bill: Um, since it's Weekend Tuesday, um, can we just go home?
    Darryl: See, it's Weekend Tuesday, but it's not the real weekend. Now, look, Bill, why don't you put on that sombrero and then head on back to work?
    Bill: ...Right.
  • Sensitive Guy and Manly Man: The Sensitive Guy to White Josh's Manly Man.
  • Sweet Tooth: Repeatedly shown to love candy, and has a complete meltdown when Nathaniel bans sweets from the office.
  • Unwitting Instigator of Doom: Rebecca calling a hit on Mona was indirectly caused by him allowing her to take hormones to get her eggs. Although, in his defense, Rebecca was the one to never ask for his doctor's advice and take hormones either way, knowing the effects it could cause.

    Heather Davis 

Heather Davis

Played by: Vella Lovell

https://static.tvtropes.org/pmwiki/pub/images/heatherdavis.jpg
"What time should I come over? Not to party or anything but just like…to watch you. I kinda think you’re fascinating actually. And I’m taking abnormal psych at the JC and I think you would make like a really good paper."

Heather Davis is a psychology student at the local Junior College and Rebecca's neighbor after she moved to West Covina. She likes to observe other people's behaviors and this is initially what drew her to Rebecca. She did an entire paper and presentation on Rebecca, calling her "bonkerballs," but eventually realized that she would rather befriend Rebecca than study her.

She eventually begins to date Greg Serrano during the Christmas episode, but breaks up with him when she realizes he has feelings for Rebecca.

Tropes:

  • Advertised Extra: In season 1, at least. While she is treated as a main cast member by the opening credits, she doesn't appear until the fourth episode of the series, has no major ties to the plot besides briefly dating Greg, frequently is absent from episodes entirely and in general only contributes about as much as supporting characters such as White Josh do. This is lessened in season 2, where she becomes Rebecca's roommate, though she is still generally much less of a presence than the rest of the main cast. She's since become more prominent in the cast and has a big part in Darryl's subplot in season 3.
  • Ambiguously Bi: Heather has dated guys, but she has also remarked that she finds Rebecca dressed in a lawyer outfit hot.
    Heather: Man, she looks hot in her little legal outfit, right? I'd pound that gavel.
  • Ambiguously Brown: Heather is biracial (with a white mom and a black dad), but she's seen as this in-universe, if Kevin trying to eke her ethnicity out of her in "Oh, Nathaniel, It's On!" is any indication. He guesses she's of Indian descent.
  • Brilliant, but Lazy: She doesn't really has the drive to do anything, despite her genuine skill and smarts at doing it, she'd much rather not do anything at all.
  • Brutal Honesty: Has no problem delivering crushing truths to Rebecca about her behavior.
  • Character Development: She seems at first to be a stereotypical slacker student, but in Season 2's "When Will Josh and his Friend Leave Me Alone?" it emerges that she still lives with her parents, who adore her and encourage her no matter what. When Heather almost inadvertently becomes the face of "Miss Douche", she realizes that her parents "reward failure", and she resolves to get her own place [[spoiler: with Rebecca as her roommate.
  • The Comically Serious: In her musical numbers. Notably in "The Moment Is Me", an hopeful song which she sings with no enthusiasm whatsoever.
  • The Cynic: She's pretty uninterested in everything around her.
  • Deadpan Snarker: Sarcasm is her go-to response to almost everything.
  • The Ditherer: This is implied to be the reason for her refusing to graduate despite having been in college for eight years and having taken all her university's courses — she is unsure of what to do with her life and has been sitting on this decision for a while.
  • Emotionless Girl: She barely displays any emotion at all. Even on a sugar rush.
    Heather: [absolutely deadpan]] I like you a lot, Greg.
    Greg: [smiling] That's—that's funny.
    Heather: [still absolutely deadpan] Yeah, no, I'm, like, excited about this. I have butterflies.
  • Fatal Flaw: She avoids actual responsibilities like the plague. In no small part due to her parents "rewarding failure", she learned she never needed to take anything to the end and avoids things when they get too hard. She grows out of it in season 3, adopting responsibilities as a manager in Home Base.
  • Happily Married: She and Hector get married in Season 4, on a whim, during her lunch break, so she could add him to her health insurance plan. Despite this total lack of planning, their marriage appears to be rock solid.
  • Hidden Depths: Heather is actually very observant and sensitive to the feelings of others.
  • Jerk with a Heart of Gold: Heather's sarcastic, blunt, and unemotional, and... actually pretty nice, once you get to know her.
  • Not So Stoic:
    • Heather breaks down and almost cries when she confronts Greg about rushing off to LA to admit his feelings to Rebecca. She's also visibly panicked when Rebecca nearly throws herself off a cliff at the end of season two.
    • When heavily pregnant and emotional about it in season three, Heather actually breaks down and cries openly. Hector is as stunned as the audience. She also cries tears of joy at her wedding to Hector in season four.
  • Out of Focus: She doesn't get written out so much as just not having much to do with the plot in the latter half of the first season. However, she comes back into focus in Season 2, with she and Rebecca becoming roommates.
  • Pet the Dog: She pretty much selflessly volunteers to bear Darryl's child, without even asking for money or anything. Subverted when she points out that she agreed to it on a whim, and later acknowledged that she did not think through all the implications first.
  • Shipper on Deck: By the end of the show she's solidly on team Nathaniel/Rebecca.
  • The Stoic: She rarely shows her emotions outwardly. In "Nathaniel and I Are Just Friends!" she admits she was stoic as a baby — she didn't even cry and her parents thought something was wrong with her.
    Heather: I was just a super chill baby!
  • Triumphant Reprise: Reprises Greg’s ode to self-loathing, “Settle For Me,” as an ode to self-love, “DON’T Settle For Me.”
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    Valencia Perez 

Valencia Maria Perez

Played by: Gabrielle Ruiz

https://static.tvtropes.org/pmwiki/pub/images/valenciavalderrama.jpg

Women gotta stick together
And tell each other the truth-
The truth is you're all fat sluts,
And that's called sisterhood.

Valencia Perez is Josh Chan's long-term girlfriend. They have been going out since high school, although they did have a small break when Josh went to summer camp (and dated Rebecca) ten years ago. Valencia is a yoga instructor and very vain. She doesn't like other women and she thinks ghosts are obsessed with her. While initially Rebecca befriended her, the friendship soured and Valencia came to dislike and distrust Rebecca.

Tropes:

  • A-Cup Angst: She's jealous of Rebecca's... talents, and even thought of getting implants at one point. Considering how proud she is of her looks, that says a lot.
  • Adorkable: Not often, but she has her moments. Her victory dance after Josh tells her he wants to propose definitely qualifies.
  • Alpha Bitch: She often acts like an adult version of a high school queen bee, especially in the first season. She has no Girl Posse to speak of as she can't help rivaling and intimidating other women. Josh's (mostly male) friends can barely put up with her.
  • Background Halo: When Valencia forgives Josh for kissing Rebecca, she stands up in front of a big picture of the Virgin Mary and, naturally enough, acquires one of these.
  • Betty and Veronica: Played with. While she's the strikingly beautiful ice queen in contrast to the pretty but less glamourous and friendly Rebecca, she is also Josh's childhood friend who has earnestly waited her entire life for him to propose to her, giving her traits of both a Veronica and a Betty.
  • Bi the Way: Revealed to be in a relationship with a woman in "Nathaniel and I Are Just Friends!". Said girlfriend, Beth, was a former client of hers.
  • Big Bad: Fairly brutally subverted. She's Rebecca's primary obstacle in wooing Josh, but her status as a villain is completely dependent on the assumption that Rebecca is "meant to be" with Josh, something that the show repeatedly addresses. She comes off as vain and controlling, but never actually does anything wrong. It gradually becomes obvious that, from Valencia's perspective, Rebecca is trying to manipulate and seduce her boyfriend, breaking up a 15 year relationship. In season 2, as she gets more screen time and development, her previous demeanor seems much more justified, and Rebecca's earlier actions feel increasingly awful.
  • Bitch in Sheep's Clothing: Used to be this before changing her ways. Combined with Selective Obliviousness, gives the following:
    Josh: [after the gang has been to a movie about a cancer patient] I totally relate to Chad, the sensitive jock who eats clean and journals hard.
    Hector: Yeah, and I'm so the bad-boy rich kid who sleeps with that hot girl in remission.
    Valencia: And I am so exactly like that caring nurse who donated her bone marrow.
    Greg: You didn't feel any connection to the vain yoga instructor?
    Valencia: [stony stare] She was fat.
  • Characterization Marches On: In the first season, she mentions that she "doesn't like humor." While she Took a Level in Kindness later, that part of her character was abandoned and forgotten almost immediately.
  • Childhood Friend Romance: She and Josh have been together since they were eleven, and have likely known each other for even longer.
  • Clingy Jealous Girl: Forbids Josh from having female friends due to a fear of having them try to steal him from her. She's actually not wrong, since that's exactly what Rebecca is trying to do.
  • Defrosting Ice Queen: Starting in Season 2, Episode 5, she starts bonding with Rebecca and she becomes friends with her and Heather.
  • Do Not Call Me "Paul": She changed her first name from Maria to Valencia.
  • Even the Girls Want Her: Rebecca can't help but acknowledge her beauty and sex appeal. It's one of the many reasons why she hates her.
  • Fallen Princess: As of her breakup with Josh at the end of season 1.
  • Female Misogynist: Valencia sees other women as competition who are just jealous of the attention she gets from men. "Women Gotta Stick Together" is almost nothing but her insulting or berating other women. She gets better.
  • The Friend Nobody Likes: Subverted. None of Josh's friends really like Valencia because they can see how self-centered she is. She in turn doesn't have female friends, because she feels threatened by them. By season 2, she has realized this about herself and is doggedly trying to become friends with Rebecca and Heather.
  • Happy Dance: After Josh tells her he's finally going to look for an engagement ring. Valencia does a good job at staying calm and subdued in her happiness... until Josh leaves the room. See for yourself.
  • Happily Married: with Beth, at the end.
  • Hate Sink: Deconstructed. Her unlikable personality makes it much easier for the audience to take Rebecca's side in their feud when, in reality, Rebecca is the sole person responsible for their feud existing at all. By season 2, she's mellowed out somewhat and has become much more sympathetic.
  • Heartbreak and Ice Cream: After her broken engagement with Josh she buries her pain in pastries. She gains a tiny amount of weight but for her that's a big deal.
  • Hidden Depths:
    • Is steadily revealed to genuinely love Josh, and, despite appearing to be the domineering one in their relationship, has actually been patiently allowing him to string her along for years out of a hidden desire to get married to him.
    • After breaking up with Josh she becomes lonely, depressed and binges (in a small way) on comfort food, and then is persuaded by Rebecca that they are both the victims of Josh's exploitation, whereupon she becomes friends with Rebecca.
    • The extent to which she put up with Josh's basic lack of care for her comes out in a throwaway remark in season 2, when she is disgusted to see that Josh has bought his new girlfriend flowers. She might have been rather pushy and controlling in season 1, but Josh was hardly a model romantic partner either.
      Valencia: The only time he got me flowers was prom night. Blue carnations from a gas station. From a bucket. In return, I gave him my virginity.
    • In the aftermath of Rebecca's suicide attempt in 3x05, it seems as though she's using her friend's misfortunes for her own attention-seeking agenda. However, as it turns out, it was her outlandish way of coping. At the end of the episode, after she, Paula, and Heather, all believed Rebecca had attempted suicide again when she wouldn't respond to them from behind a locked door (she had earphones on), Valencia had a full breakdown. She stated that she'd never had a real friend before and wanted Rebecca to promise she'd never do that again because she was so terrified of losing her first genuine friend.
    • In Season 4's "I'm Not The Person I Used To Be", Heather is delighted to learn that when Valencia was dating Josh in high school, she was secretly deeply in love with someone else the entire time, but nothing came of it. It turns out to have been the pre-priesthood Father Brah, who never got Valencia's love note because it was in his varsity jacket in the trunk of Hector's car. Father Brah and Valencia have a fond moment of closure, recognizing that they're both happy in their existing relationships: she with Beth, he with God.
  • I Am Not Pretty: After she's turned to baked goods in the aftermath of her breakup with Josh, she believes herself to have become grossly overweight. Immediately Lampshaded:
    Valencia: Okay, can you stop talking about my weight? I get it, I'm a ginormous 6, junior 5/7, so just shut up about it.
    Rebecca: Okay, fine. Just a fun fact, the national average size is actually a 12, so, you know, you're — you're very petite.
  • Inferiority Superiority Complex: It's clear that she's a lot more insecure than her haughty demeanor would indicate.
  • It's All About Me: Horrendously self-centered. She tried to get Josh to propose at his sister's wedding specifically to steal some of their thunder. Josh actually realizing how she never listens or cares about anyone else makes him break up with her.
  • Horror Hunger: In an early episode she reveals she has some kind of eating disorder as has felt like she's starving since it started in 1998. After breaking up with Josh she starts eating more and (probably not coincidentally) becomes much nicer as well.
  • Jerkass: Generally a mean-spirited and self-centered person who looks down on everyone, her boyfriend included. Her more humanizing moments make her actions more relatable, but no more sympathetic. Season Two is slowly phasing this out, making her pitiable and more three-dimensional.
  • Jerkass Has a Point:
    • For all of her horrible qualities, she's completely right to suspect Rebecca of wanting to steal Josh for herself.
    • She's also right that Josh's refusal to choose a direction for their relationship is pretty ridiculous considering how long they've been together. By the end of the first season, you sort of want to shake him and say, "Propose to her or break up with her, already!"
  • Jerk with a Heart of Gold: She becomes this from season 2 onward.
  • Lean and Mean: She's model thin in contrast to the noticeably curvy Rebecca. The show repeatedly emphasizes her smug sense of superiority about being thinner than other women as one of her many negative traits. She seems to have been taking Josh's breakup badly, given her return in Season 2's "When Will Josh and His Friend Leave Me Alone?": Rebecca is stunned to see Valencia buying a donut in public and stuffing it into her mouth. In mid-munch, she catches Rebecca's eye, and her "Oh, FFS" look is priceless.
  • Ms. Fanservice: Her gorgeous looks and fantastic body are constantly the center of attention, both due to her love of showing off and Rebecca's jealousy.
  • No Sense of Humor: When Rebecca makes a joke in an attempt to endear Valencia to her, Valencia is at first confused, then says "Oh, you were making a joke... Yeah, I think you did that once before. Sorry, I don't like humor."
  • Put on a Bus: Subverted. Although she moves to New York partway through Season 4, she only spends two episodes there before returning to West Covina for the rest of the series... of holidays. Despite the move, she still manages to appear in both of these episodes anyways; in the first, she video-chats with Rebecca and Heather, while in the second, Rebecca comes up to the Big Apple for Naomi's charity event and stays at Valencia's place.
  • The Rival: Passive aggressive competition becomes a common occurrence between her and Rebecca over time. Later subverted, as Rebecca realizes Valencia isn't the enemy, and the two bury the hatchet.
  • Secret Chaser: Gradually becomes more intent on exposing Rebecca's desire to have Josh for herself over the course of the first season.
  • Shameless Fanservice Girl: Provocatively struts around in a skimpy bikini for no reason beyond making Rebecca self-conscious.
  • Shipper on Deck: By the finale, she's a Greg/Rebecca shipper.
  • Sir Not-Appearing-in-This-Trailer: She's notably absent from the opening sequence of season one despite being one of the most important characters in the series, to the point of having two solo musical numbers all to herself. Justified in that she's the closest thing the show has to a consistent antagonist in season 1, and would thus be out of place as one of Rebecca's cartoon "new friends".
  • So Beautiful, It's a Curse: Valencia gets really sick of people making passes at her and actually feels hurt when Rebecca does it.
  • Social Media Before Reason: She obsesses with recording and streaming everything in season 3, which she later admits is out of insecurity.
  • Suddenly Sexuality: She gets together with her girlfriend Beth during a Time Skip, and her bisexuality was never mentioned before.
  • Teacher/Student Romance: She did "hand stuff" with her English teacher when she was in high school. She claims it was no big deal and it was apparently consensual, but Rebecca is understandably freaked out by this, and points out that this was not only not okay for her teacher to do, but also may have been statutory rape, depending on how old Valencia was at the time. She then asks if he was ever fired or if Valencia knows if he had relations with any other students. Valencia, for her part, honestly doesn't seem to get why Rebecca's making a fuss.
  • Took a Level in Kindness: Did she ever! She goes from being a rather bitchy and controlling girlfriend to Josh, and The Rival to Rebecca, to being a genuinely kind, thoughtful, and loving friend.
  • Villainy-Free Villain: From Rebecca and Paula's initial POV, she's presented as the Alpha Bitch, Romantic False Lead, and they feel justified trying undermine her and steal Josh away. The reality is that Rebecca hates her because she's good-looking and dating Josh, and that's pretty much it. While she is arrogant and frequently condescending, her actions toward Rebecca are 100% justified. Rebecca eventually realizes this, and they end up becoming friends. Ironically, her most questionable actions all come as a direct result of hanging out with Rebecca.
  • Visual Development: In season two she dials back on the bold makeup and skimpy clothes she was frequently seen wearing in season one, to reflect her being a friendlier and less intimidating character.

    "White Josh" Wilson 

Josh "White Josh" Wilson

Played By: David Hull

https://static.tvtropes.org/pmwiki/pub/images/whitejosh.png
"I didn't come out of the closet until I was twelve. Those were some tough years."

One of Josh's friends. So named because he looks like Josh, except he's white. Oh, and his name is also Josh. He works at a gym, walks around shirtless a lot, and is gay.

Tropes:

  • Age-Gap Romance: With Darryl. White Josh is 26 and Darryl is in his forties. Season 2 shows that he's just generally got a thing for older men, with most of his ex-boyfriends being Darryl's age or older.
  • Amicable Exes: Although he and Darryl are initially awkward around each other after they break up, they quickly realize that both of them still want to be friends.
  • Ascended Extra: Initially just another one of Josh and Greg's interchangeable bro friends, but goes on to be a major supporting character and Darryl's primary love interest. He has been promoted to the main cast starting in season 3.
  • Beta Couple: He and Darryl become one, as their relationship is far healthier and more stable than any other relationship on the show.
  • Brainless Beauty: Subverted. He initially comes off as a good-looking space cadet (very much like Josh Chan, hence the nickname). But he's quickly revealed to be one of the more perceptive and self-aware characters in the show.
  • Bunny-Ears Lawyer: His obsessions with working out and eating protein are somewhat questionable, but he remains one of the most competent characters on the show despite them.
  • Closet Key: He makes Darryl realize his bisexuality.
  • Fatal Flaw: Despite all his good qualities, he tends to be too laid-back and unambitious (much like the rest of his friends). He spent 2 years working on a recipe for nutrition bars made from ant protein, and still didn't have a clear plan for what to do with it. Darryl created a brand and a mascot and start marketing it in an afternoon because he was bored.
  • Formerly Fat: He was a fat kid growing up before resolving to get in shape. An exaggerated example, as he made the decision to get in shape when he was only seven years old.
  • Gym Bunny: Obsessed with fitness, and at first, was almost always in the middle of working out.
  • Hidden Depths: Comes off as nothing more than a muscle-headed surfer bro initially, but is steadily revealed to be a mature, intelligent and empathetic guy, as well as the show's primary Only Sane Man.
  • Has a Type: His exes are all somewhat similar to Darryl, being older and with facial hair.
  • Inelegant Blubbering: In his duet with Nathaniel, "Fit Hot Guys Have Problems Too", both break down crying, stating that they'll ugly cry and it's really not pretty at all.
  • Insecure Love Interest: For Darryl, as it turns out in season 2. He starts becoming afraid of being a boy toy for Darryl's mid-life crisis and blooming sexuality. He is specially upset of the fact Darryl seems to never so much as mentions him to Madison. Though it turns out that Darryl was trying to not push him into something serious.
  • In-Series Nickname: "White Josh" itself is one. In season 2, he begins going by "Whijo" as well.
  • Likes Older Men: His exes are all middle aged-ish and he's in his 20s.
  • Mellow Fellow: He's chill at all times and acts with calm nonchalance during even the most stressful situations.
  • Mr. Fanservice: He's in great shape and is constantly shirtless. Ironically, despite looking very similar to Josh, Rebecca finds his body unsightly.
  • Nice Guy: He's not a walkover, but he's friendly and kind, and he gently warns Rebecca about the potential danger of getting too involved with Greg.
  • Not So Above It All: White Josh rolls his eyes at all the messy romantic drama surrounding him, but partakes in it by the show's end — he suggests the three suitors' Bachelor-esque final dates with Rebecca because it amused him and escalates the betting pool. In "Love's Not a Game":
    "Love is what unites me and you and him and her and him and him and me as well
    JK LOL
    Let's do this!"
  • One Steve Limit: The aversion of this trope is the source of his nickname.
  • Only Known by Their Nickname: Since he has the same name as Josh, everyone calls him "White Josh."
  • Only Sane Man: Much more so than even Greg. He's generally a friendly, mature sensible and caring guy, but he also isn't the slightest bit afraid to call out even his closest friends when they're in the wrong. He is guaranteed to serve as the voice of reason to anyone he is sharing a scene with.
  • Rightly Self-Righteous: He's genuinely a lot more together and clear-headed than most of the other characters. His only character flaw is that he's a little too aware of that at times.
  • Straight Gay: All his friends know he's gay, though, so he doesn't feel the need to tell anyone.
  • Walking Shirtless Scene: He's shirtless a lot in the early episodes.

     Nathaniel Plimpton III  

Nathaniel Plimpton III

Played by: Scott Michael Foster

https://static.tvtropes.org/pmwiki/pub/images/crazy_ex_girlfriend_scott_michael_foster_nathaniel_1.jpg

"Come on, let's quickly
have intercourse...
(Let's quickly have intercourse)
So I can move on
with my life..."

Nathaniel is the new boss at Whitefeather and Associates in season 2. He's a ruthless and money-minded lawyer who reminds Rebecca of all she tried to escape in New York.

Tropes

  • Abusive Parents: He lives in terror of his father who can reduce the usually confident and haughty Nathaniel to an emotional wreck in seconds.
  • Amoral Attorney: Has no qualms with destroying people's lives if he gets something out of it.
  • Beauty Is Bad: Nathaniel is attractive, suave, and possibly a sharkier lawyer than the ones in New York. Lampshaded heavily; Paula remarks that "a man with a face that perfectly symmetrical has no soul", and Maya describes him as "suspiciously good looking in ways that normal people are not!"
  • Belligerent Sexual Tension: With Rebecca, whom he's always clashing with — but there's an obvious undercurrent of mutual attraction. They act on it in the second episode of season three.
  • Broken Ace: A handsome Stanford graduate who is already in charge of his own law firm in his twenties... and has a crippling fear of letting his father down.
    Nathaniel: It's over. Get out of the pool, wash off the chlorine, and apologize to your father!"
  • Card-Carrying Villain: Downplayed. Is proud to call himself a Slytherin (see Closet Geek), who are villainous more than not.
  • Character Development: He goes from a haughty Amoral Attorney to a genuinely nice guy. Rebecca breaking up with him, seemingly for the final time, because of how toxic they become with each other in season 4 is the biggest catalyst; after this event he actively tries to be a nice person.
  • Closet Geek: He admits to having read all the Harry Potter books in one week and regards them as modern classics.
  • Cyborg: Played for laughs, in that he has a glucose monitor embedded into the soft flesh of his abdomen. A very impressed Darryl remarks:
    Darryl: You're a machine.
  • Daddy Issues: As much as he'd like to pretend otherwise, his father had exceedingly high standards and constantly pushed Nathaniel to meet him. Daddy Issues is in fact one of the reasons for his sympathy for Rebecca, who has a deadbeat dad.
  • Deadpan Snarker: Often though his quips tend to be crueler.
  • Defrosting Ice Queen: He starts to warm up after meeting Rebecca, and even makes friend with George, the employee who he fired twice.
  • Even Bad Men Love Their Mamas: Nathaniel genuinely loves his mother and wants closure when he believes she tried to commit suicide when he was 10.
  • Freudian Excuse: Much of Nathaniel's Jerkass behavior is clearly rooted in his very unhealthy upbringing. His father despises both "weakness" and "unpleasantness", meaning that Nathaniel lives in fear of his constant disapproval and can never address anything that hurts or upsets him. This extends to his mother's suicide attempt when he was ten years old. Nathaniel found her unconscious, she went away for a month, and 20 years later his parents still refuse to admit that anything happened.
  • Freudian Slip: When he and Rebecca talk about their affair, Rebecca mentions to love their current relationship, which almost prompts him to ask if she loves him.
  • Good Feels Good: Although his initial attempts at being nicer were inspired by his lingering feelings for Rebecca and a tough heart-to-heart with Heather, he quickly discovers that he actually enjoys what it feels like to help others.
  • Inelegant Blubbering: In his duet with White Josh, "Fit Hot Guys Have Problems Too", both break down crying, stating that they'll ugly cry and it's really not pretty at all.
  • Ivy League for Everyone: went to Stanford- which while not an Ivy League - still continues the trend of successful characters going to very prestigious universities.
  • Jerkass: Nathaniel he generally acts condescending towards everyone he speaks to and doesn't bother remembering the names of anyone who he considers below him. He also regularly mocks Josh for looking like a water cooler for no other reason than to mess with Rebecca.
  • Jerk with a Heart of Gold: However, he does have some humanizing moments, mostly centered around the impossibly-high standards he holds himself to in order to make his father proud.
    • The biggest moment is probably when he flies Rebecca's dad in on his private jet for her wedding to Josh.
    • Taken further when he gets Heather to take him on a road trip to the beach, but won't tell her why he's clutching a padded envelope. It turns out to contain the ashes of his beloved Austrian nanny, Heidi, who'd recently died and to whose family he promised he would scatter her ashes in the ocean because she and he used to have fun there.
  • Ladykiller in Love: The beginning of season three makes it very clear that his sexual feelings for Rebecca have turned into romantic ones.
  • Manchild: He may act the manly man, but deep down he only wants to take naps, read Harry Potter and go to the zoo. More seriously, he's very emotionally immature, as his struggles with his feelings for Rebecca show.
  • Mr. Fanservice: He's very fit and muscular, even getting a song all about the subject.
  • Never My Fault: After spending some time with Rebecca, he realizes that a lot of his behavior is appalling, but justifies it because they were both raised by bad parents. They have a duet, literally titled "Nothing is Ever Anyone's Fault".
  • Not So Above It All: He's nowhere near as masculine and sensible as he'd like to appear.
  • Odd Friendship: Develops this with Heather after going on a road trip with her.
  • Only Sane Man: Frequently lampshades how cartoonish the rest of the firm are, though subverted as he can be as crazy as the rest.
  • Pet the Dog: Rebecca was the only person he showed affection towards. Later he gets a friendship with George.
    • When Rebecca is going to get married he helps her dad get there using his private jet. Though this is soured somewhat as in the next episode he goes around bragging about how nice it was for him to do that.
    • One of his early musical numbers reveals that he loves to spend time at the zoo and sometimes even bottle feeds the baby pandas, which is almost a literal Pet the Dog moment.
    • A huge one in season four, when he gets an entire episode about his plans to win Rebecca back. At the end of the episode, he has the very painful realization that she's moved on, and he needs to let her go and be happy for her.
  • Preppy Name: "Nathaniel Plimpton III" is about as preppy as they come.
  • Pursue the Dream Job: In the end, he quits law to work at the zoo.
  • Rated M for Manly: He tries very, very hard to give off this vibe but he just comes across as overcompensating and it's clear none of the other characters see him as being very impressive or have much respect for him.
  • Real Men Hate Sugar: He's a believer in this as he bans sweets from the office and refuses to eat any himself, freaking out after he eats some chocolate.
  • Rich Bastard: Comes from a wealthy family and is a pretty big dick. He's starting to get better.
  • Token Evil Teammate: While most of the characters have their quirks, Nathaniel was perfectly willing to kill someone. He does mentions in season 3 finale he probably wouldn't go all the way with it, but still.
  • Token Minority: Inverted. In his first episode, the other characters sing about how they can't be expected to care about some "straight white male" - of which he is indeed the only one among the major characters at that point.
  • Took a Level in Kindness: Begins to do this after opening up to Heather about his upbringing. Subverts it somewhat by continually pointing out to people "I'm nice now", until Greg advises him to stop saying it out loud.
  • Tyrant Takes the Helm: At first, he's the firm's ruthless new boss. He mellows out as time goes on.
  • Weight Woe: He's obsessed with his appearance and freaks out if he eats any unhealthy food or gains weight.
  • "Well Done, Son!" Guy: Nathaniel's family is highly successful (known as the 'perfect Plimptons') and it's obvious he's under a lot of pressure from his dad to live up to their reputation.
  • Your Cheating Heart: After starting a relationship with a former Stanford friend, he begins an affair with Rebecca that goes on for 8 months. Mona reveals to know about it much later, and that she was hoping he'd try for real a relationship with her.

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