History TearJerker / YoureTheWorst

** 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 [[{{Jerkass}} Becca]] and [[ManChild Vernon]] as her parents. This season especially has really hammered in just how [[AwfulWeddedLife miserable]] Becca and Vernon are in their marriage and the only thing keeping Vernon from going ScrewThisImOuttaHere is because he loves his daughter and does not want her to get screwed up by Becca too much.

* "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 genuine 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.

** [[spoiler: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 [[DeathEqualsRedemption he knew he didn't have much time left]]. And Jimmy ''still'' cut off all contact with his family after they left]].
** [[spoiler: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''': [[spoiler: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!]]

* "Twenty-Two" is a very difficult episode to watch as it follows Edgar [[spoiler: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 [[spoiler: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.