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Tear Jerker / You're the Worst

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  • Gretchen's struggle with clinical depression throughout Season 2 is heartbreakingly familiar to anyone who has a similar condition or loves someone who lives with it. It's all the more sad to watch because despite the fact that she tells Jimmy not to try to fix her, he doesn't understand and is painfully insensitive at times.
    Jimmy: I am asking you to let me vent.
    Gretchen: I can't.
    Jimmy: You mean you won't.
    • It's even worse because when Lindsay realizes what's going on and asks if Gretchen is going to tell Jimmy, Gretchen responds, "I can't tell him my brain is broken." Feeling broken or defective is very, very common among mental illness sufferers.
  • Mixed with heartwarming, Jimmy's interactions with his father when his sisters aren't around in "A Right Proper Story". Despite their obvious differences, his dad is trying to communicate, and Jimmy is speechless for a moment when his father tells Nina to read Jimmy's book. Jimmy, who spent most of "Equally Dead Inside" upset and angry with his father because he never heard anything back after sending a copy, actually tears up.
    • The end of "Fix Me, Dummy" makes this so much more tragic with the reveal that Ronald Overly died shortly after that visit. It seems entirely possible that he was trying to reconcile with his only son because he knew he didn't have much time left. And Jimmy still cut off all contact with his family after they left.
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    • Driving it in even harder is the end of "Bad News: Dude's Dead," when Jimmy calls his father, not knowing he's dead, supposedly to unleash all his anger at him, but then:
      Jimmy: Hey, Ronnie! It's your son! You're probably in the pub, passed out in a stall over a half-eaten Scotch egg in lard sauce, but I just wanted to let you know... (tenses up, ready to unleash his emotions, then, almost child-like) I sold a book, Daddy!
  • A subtle one through all of "LCD Soundsystem". Gretchen, in the throes of a feeling of emptiness due to her depression, has taken to watching a married couple that lives nearby from the shadows. They appear to have everything figured out; a pair of healthy functioning adults who've settled into domestic bliss after a fun youth. But this fantasy of wanting to have what they have is shattered when she sees that they have just as many hang-ups and insecurities and regrets of their own too (the husband especially, who misses his carefree bachelor days and admits as much to Gretchen). The final shot of the episode is of Gretchen crying as she leaves their house with Jimmy not even noticing.
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  • "Twenty-Two" is a very difficult episode to watch as it follows Edgar struggling to get through his day without medication to relieve the symptoms of his PTSD. Jimmy's sheer ungratefulness for everything he does suddenly takes on a completely different light. And the whole scene in the Veteran Affairs office where he's denied a new experimental treatment due to discontinuing his medical regimen captures every bit of his frustration.
  • "You Knew It Was A Snake" has all the underlying issues of the show's three main couples (Jimmy and Gretchen, Paul and Lindsay, Dorothy and Edgar) brought to light, and both parties confronting each other with them throughout the whole episode. It is by far the most raw and emotional episode of the show so far.
    • Edgar isn't happy with Dorothy's lack of support for his newfound career as a writer for Doug Benson, which is not helped when she makes an insensitive remark about him only being hired for his race. He goes on to accuse her of only liking him when he's low and struggling, and she tearfully reveals that she's actually jealous of how far he's gotten in such a short amount of time while she's been working in comedy for years struggling to get a break and has nothing to show for it, and is completely certain that she's never going to succeed, especially at her age.
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    • Paul, having just found out that Lindsay secretly got an abortion and has been planning to leave him, finally has gained the courage to call Lindsay out on all her crap and has a hard emotional breakdown as he realizes the magnitude of how wrong she was for him. Lindsay then sadly but simply retorts, "You knew it was a snake when you picked it up," claiming that he has no one to blame for all he went through with her but himself because he let his shallow attraction to her and consuming desire for a family blind him to the very obvious signs that they were not right for each other. Paul does walk out with the last word when Lindsay asks for him to get rid of their prenups: "You stabbed me, you cuckolded me, and you ruined my life. Better lawyer up, bitch."
    • While Gretchen and Jimmy discuss the "cons" they shared with each other in the previous episode, they attempt to eavesdrop on the other arguing couples, after which they come to terms with how dysfunctional they are themselves. By the end, their conversation has reached the point where they wonder if their relationship, such as it is, could be considered a success or a failure. Gretchen does get encouraged a bit as Jimmy admits that the central story of his "erotic tales" book was inspired by her, though they do admit at the end that they haven't really addressed the state of their relationship at all throughout the day and despite everything they've said to each other.
  • "No Longer Just Us," the season 3 finale:
    • Dorothy leaves Edgar in spite of him debating on whether to advance his career even if it looks like he's leaving her behind in the process. He takes the job anyway, knowing that it wouldn't help him, and by extension her, to compromise this big opportunity for her sake, but she takes the decision away from him and is planning to move back home to Jacksonville, saying that he never should have even considered that an issue if they were really in love.
      • To a lesser extent, there's the fact that Dorothy's decision to leave is heavily motivated by her sad acceptance of the fact that her dream of being a successful actress is dead. Her line about how "Not everybody gets their dream" can hit hard for anyone who can relate to that, especially if they, like Dorothy herself, tried but still failed.
    • Paul and his lawyer discuss the terms of his divorce from Lindsay. The proceedings are interrupted by Becca and Vernon, along with their newborn daughter, and Paul sadly looks on as Vernon brushes him off regarding their plans to move to Mexico, and Becca savagely insults him and bluntly says he's not part of their family anymore. After Paul leaves, Lindsay and Becca have a serious conversation where Becca admits to being jealous of Lindsay for her regained freedom, and laments all the dreams she feels she traded in exchange for becoming a wife and mother, and how she can't indulge herself anymore for the next 18 years.
      • A Fridge Tearjerker when you really think on it: poor baby Tallulah has Becca and Vernon as her parents. This season especially has really hammered in just how miserable Becca and Vernon are in their marriage and the only thing keeping Vernon from going Screw This, I'm Outta Here! is because he loves his daughter and does not want her to get screwed up by Becca too much.
    • Gretchen is intrigued by the story of a murder that happened near Jimmy's place, and he agrees to follow her as she tracks the story down. In the evening, they arrive at the scene of the crime, only for Jimmy to reveal that he made the whole thing up... after which he gets down on his knees and proposes to her. She gladly accepts, and Jimmy puts the ring on her hand, but when Gretchen happily declares that they can be a family together, Jimmy freaks out and drives away, leaving Gretchen alone on the hill.
  • The first episode of Season 4 picks up three months after the events of "No Longer Just Us" and it's not pretty.
    • Jimmy, out of guilt, has fled Los Angeles and holed himself up in a desert retirement community, living out of a mobile home and completely off the grid. No one knows why he's here, and his only "friend" there is a 71 year old grouch of a man with a hot rod who barely tolerates him. He's finally pushed to go back when seeing the barrage of text messages, voicemails and missed calls, and realizing said "friend" could very well be his future.
    • Gretchen meanwhile has undergone full-on Sanity Slippage, living with Lindsay in her new studio apartment, and has holed herself up there for the whole three months that went by. She's utterly distraught by Jimmy's sudden abandonment and it's not hard to see why especially since she has no means of being able to contacting him.
  • "Odysseus"
    • As happy as he is to see that Jimmy's back, Edgar's anger as he describes how worried sick he was by Jimmy suddenly disappearing and going completely silent on all communications for three whole months (to the point of wondering if he was dead), as well as how devastated Gretchen has been during this time is very heartrending.
    • Jimmy chases after Gretchen, and he apologizes to her, admitting he did wrong by her and was a coward... but then messes that up when he explains how her saying they could become a family was what made him leave her on that hilltop. Gretchen walks off, making it clear Jimmy is not so easily forgiven.
  • "Not a Great Bet". Just... everything about it, especially the ending.
  • "A Bunch of Hornballs": Lindsay, at Gretchen's behest, decides to throw herself a party celebrating her now finalized divorce with Paul and invites her coworkers to the festivities. However, she finds out from the office Butt-Monkey Carl that not a single one of them likes her. Then Becca drunkenly insults Lindsay through the party, and it's all capped off with Paul crashing the party to tell Lindsay that she has no one to blame but herself for being a failure at life. Even if the jerks have a point, it's still pretty sad to see Lindsay get shot down like this, especially as she has made some progress.
  • "Worldstar!": While Becca and Lindsay's mother Faye comes to visit them, the two immediately get to competing for her attention. It becomes pretty obvious that Faye's terrible negligence of her daughters (and her blatant lack of really caring for them) is what led to them being so utterly messed up. It's all capped off with Becca breaking down sobbing as she admits how miserable she is in her marriage to Vernon and her life is a sham, especially because all she wanted to do was show Faye that she had her life all sorted out.
  • "From The Beginning, I Was Screwed": Lindsay has to help Paul out of a jam, and since he's drunk, he needs to lay down. She sets him on her bed, and for the first time since their split, they have a genuinely heartfelt conversation as Paul laments missed opportunities regarding having a family, showing Lindsay one of the video journals he made for their baby. Even Lindsay is moved to tears.
  • "Like People": At the start of the episode, Gretchen wakes up in an empty hotel room, furious and hurt that Jimmy might have left again. It turns out that he was just getting breakfast, but she still doesn't trust that Jimmy won't just up and leave at the first sign of trouble. Jimmy, who simply wanted to show her a good day, can't understand why she's treating him like this. Both Sides Have a Point, yes, but neither can see the other's perspective.
  • "We Were Having Such A Nice Day"
    • The nasty argument Gretchen has with her mother, Vanessa. After Vanessa hijacks her and Lindsay's day plans, Gretchen finally explodes at her, demanding to know why she has always been so dismissive of her chaotic behavior. All Vanessa could say is how miserable she is with her own life and how she conceals her true emotions. Even after she reveals her suicidal thoughts, Gretchen's mother just tells her revealing such things would drive people away. You could feel the utter hatred Gretchen has towards her mother.
    Vanessa: Life is good, Gretchen. I don't know why you have to make it so difficult for yourself.
    Gretchen: (somberly) I don't make it difficult it is difficult.
    • Edgar plans Jimmy a thoughtful "day before the wedding" that he ends up enjoying thoroughly, even acknowledging, after all these years, how good of a friend Edgar has been to him. This finally encourages Edgar to speak his mind and be honest as well... he begs Jimmy not to go through with the wedding, as he's paid attention through the years just how badly the two could end up destroying each other. Jimmy (on the verge of tears) is furious at this and tells the man he just called his best friend that he never wants to see him again.
    Edgar: You love each other, but that's not the same as being good for each other!
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