- Adorkable: Jimmy. It pops up when he's really enthusiastic about something. Specifically, his Halloween costume in "Spooky Sunday Funday", and his cheesy ragtime performance at the speakeasy in "The Last Sunday Funday".
- Awesome Moments:
"Wow. I'm screwed up because I watched my friends die. You're screwed up because you're just really lame."
- "Sunday Funday": Edgar has to deal with some hipster and his crew hijacking his Sunday Funday itinerary. When Edgar calls him out on it, the hipster breaks down and says he's stressed out from trying to impress his shallow friends every weekend. Edgar's reply is possibly his finest moment:
- "You Knew It Was a Snake": Paul telling Lindsay that she "better lawyer up" because she stabbed him, cheated on him, and ruined his life and he's going to make her suffer in their divorce.
- Base-Breaking Character: Lindsay. While it is generally agreed upon that she's the funniest character on the show, there is a split in the fandom between those who find her naive stupidity endearing and those who think she's an annoying and dangerous idiot and a borderline Poisonous Friend. Those in the latter camp are especially heavily critical of how shockingly easily she was let off for raping an aspiring screenwriter while the latter was drunk in Season 1 and for stabbing Paul in Season 3. It does lessen significantly after she makes great strides in her Character Development through Season 4.
- Broken Base: The Season 5 premier was quite polarizing, mainly due to focusing on two newly-introduced characters that had nothing to do with the main plot, only to reveal halfway through the episode that it was all a fake story that Jimmy and Gretchen came up with to troll their wedding planner. Some fans found it an inspired decon-recon switch of modern love stories, while others felt their patience was tested with little to gain from it.
- Expectation Lowerer: Jimmy, Gretchen and Lindsay for jerkiness, Lindsay for stupidity and Edgar and Paul for inability to stand up for themselves.
- "Funny Aneurysm" Moment:
- One of Jimmy's disparaging comments about his family in season 2 mentions "congenital lead aggression". In "Fix Me, Dummy", Jimmy's sisters send him a newspaper clipping of their father's obituary, and a Freeze-Frame Bonus reveals that he died of a lung condition resulting from working in lead mines for most of his life.
- During her breakdown in "There is Currently Not a Problem", Gretchen delivers The Reason You Suck Speeches towards the other cast members, with her speech to Dorothy being that Dorothy is "not hot enough to be the lead and not fat enough to be the funny friend" in a Hollywood movie. Along comes "You Knew It Was a Snake", and Dorothy admits her dream of being a successful comedy actress is basically dead in the water because of that reason.
- Growing the Beard: The first season was well-liked for being a subversive take on the romantic comedy genre, but the second season upped the ante by its earnest and heartrending depiction of Gretchen's struggles with clinical depression and continued its growth in the third season's exploration of the characters and their relationships.
- Hilarious in Hindsight:
- Kether Donohue used to be a voice actress in Pokémon: Diamond and Pearl. Chris Geere would later play a major character in Pokémon Detective Pikachu.
- Both Chris Geere and Aya Cash have appeared in Modern Family.
- Cash would also go on to star in season two of The Boys (2019) as Stormfront, a character who really is the worst.
- Hollywood Pudgy: Lindsay has been referred to as "Fat Lindsay," as well as "the fat best friend."
- Jerkass Woobie:
- Jimmy, albeit he leans towards being a Jerkass. As unapologetic and rude he is, his family (little sister Lily excluded) constantly mocks and insults him, and he's acknowledged to be a talented writer but is commercially unsuccessful and frustrated by the trivial side projects he has to do. Plus the reason for his Jade-Colored Glasses when it comes to relationships: he proposed to Becca and she immediately dumped him. And now his dad's dead, which he learns directly after leaving an emotional voicemail on his dad's phone.
- Gretchen. While she does mean well (for the most part), she is often shown to be extremely uncivil, self-centered, and destructive. However, she also has clinical depression, severe self-worth issues fueled by said depression, and parents who intimidate and bully her to the point that they know almost nothing true about her life.
- Lindsay as well. Similar to Gretchen, she's also incredibly self-absorbed, immature, and petty... but it's clearly shown that she has a pretty low view of herself and barely knows how to survive or take care of herself, not to mention her mother constantly neglecting her as a child and Becca's constant emotional abuse towards her. Her Character Development involves a lot of her growing up and getting out of this.
- Branching off from Lindsay, Becca becomes one in "Worldstar!" when her and Lindsay's aforementioned negligent mother is introduced, which definitely goes a long way towards explaining her behaviors. It's capped off when Becca has a breakdown, admits that she's miserable in her marriage, and her life is a sham.
- Memetic Mutation: "Sunday Funday" and "new phone who dis" are the most virulent. Sunday Funday got so popular that when the creators were asked if it would return in Season 3, they said that they should probably hang up the joke now that it's on a T-shirt at Forever 21 (and indeed, the Sunday Funday episode of Season 3 was titled "The Last Sunday Funday").
- The Scrappy: Becca. While all the other characters are jerks to some degree, they all still get some Pet the Dog moments or at least a moment of genuine humanization showing the kinder sides underneath their rougher exteriors. Becca, however, is just plain unpleasant, self-absorbed, and downright callous, with no visible redeeming feature whatsoever. She was ultimately Rescued from the Scrappy Heap for the most part in the final season when she actually built legitimate relationships with Vernon and Paul.
- Seasonal Rot: While it is acknowledged to have plenty of good points, many fans and reviewers felt that Season 4 was generally shaky and uneven compared to the strength of the seasons before and after it.
- Some Anvils Need to Be Dropped: The show does not shy away from harsh topics with regards to mental health, relationships and growing up in general. Specifically:
- Edgar's struggles with PTSD and adjusting to regular life after the war, as well as the problems he has with the bureaucracy of the Veteran's Assistance programs, are a harsh critique of how the US, for all its "support the troops" rhetoric, does not really give the troops the support they actually need.
- Therapy and treatment may sound scary and difficult, but it's what's necessary to be a functioning person if you have a mental illness like depression.
- Marriage is a very serious commitment. Just simply "liking" one another (like in Paul and Lindsay's case) is not a solid enough foundation to build off of. And for that matter, marrying someone for the sake of appearances or because society expects you to (like in the case of Becca and Vernon) will only end in misery for everyone involved.
- Arguably the thesis for the whole show: Accepting who someone is, be they a friend or a romantic partner, is not an excuse to overlook and dismiss incompatibilities, issues, and flaws that need to be addressed and fixed.
Jimmy: I have gone years successfully never picturing your penis, and now... (disgusted noise) there it is!
- In-Universe in "Try Real Hard". Jimmy is horrified when Edgar tries to talk to him about the "bedroom problems" caused by his PTSD meds.
Nina: Skiing is rough on feet!
- Also Jimmy in "Other Things You Could Be Doing", in which the state of Nina's feet is squicky enough to immediately halt an impending sexual encounter.
Jimmy: Skiing?! These things look like they got caught in the gears of a clock!
- In "Fix Me, Dummy", there is a truly nauseating scene in which Lindsey has to remove and replace Paul's bandages, complete with pulling the blood-soaked cotton out of the puncture wound.
- The very idea of Lindsay putting Paul's used condom in a freezer, heating it up in a microwave, using a turkey baster to attempt to impregnate herself with it afterward, then scalding herself painfully and trying to use a popsicle to soothe the burn is extremely cringe-worthy, even if you're a man.
- Why Would Anyone Take Him Back?: If there's one arguable imperfection in the finale that people can agree on, it's that Paul should not have remarried Lindsay, the woman who literally stabbed him in the back the last time they were together.
- The Woobie:
- Edgar plays it straightest, being an Iraq veteran who was homeless for a time and is a Nice Guy struggling with PTSD. The abuse he puts up with from Jimmy also certainly adds to it.
- Jimmy's little sister, Lily. While he got away from his batshit family, poor Lily has not. She wanted to go to university but was told that university was "a place wankers go to study poetry and fist themselves", has been working at a strip club, and is subject to constant verbal abuse and being bossed around by her sisters.
- Killian. Jimmy forgets him at the bookstore in "Insouciance". His parents separate in season 2 and his mom moves out to live with her new boyfriend, after which his dad cries all the time. In "Bad News: Dude's Dead", he reveals that his dad recently abandoned him and he's living alone in his house. He's twelve. A couple of episodes later in the season also have him begging Edgar and Jimmy for food.
- Paul. His family neglected him and Lindsay only married him for his money (and to beat her own sister to the altar), not to mention how she stabbed him. He becomes more of a Jerkass Woobie in Season 4 due to becoming incredibly spiteful and mistrusting of women in general, but considering all the crap he's gone through, it's pretty understandable.
YMMV / You're the Worst