- Edgar being the Shipper on Deck for Jimmy and Gretchen. Even though their being together goes against all of their natural instincts, Edgar knows that despite their reluctance to go for it, they would be better off for it. He's even willing to put Jimmy in a headlock to get that through his head:Edgar: I'm sorry I have to do this. Now, I don't mind you being jerky with me because I know you care.Jimmy: What the... No, I don't.Edgar: Yes, you do.Jimmy: You're just an animal living in my house.Edgar: But Gretchen stayed, okay? You say she forced you, but we both know there's not a person on this planet that's ever had a good outcome trying to force you to do anything. She stayed, man. And that means something, whether you want to admit it or not. [beat] I'm gonna let you go now.
- Aya Cash's portrayal of Gretchen's struggle with depression is seriously underrated. This is best exemplified in how two simple words at the end of "Other Things You Could Be Doing" is enough to make up the most heartwarming scene of the series so far:Gretchen: You stayed?
- Leading into the above, Jimmy bailing on Nina after Gretchen essentially tells him to go have fun because he doesn't deserve to be stuck with her. He instead builds a pillow fort around Gretchen and lies in it with her.
- At Becca's baby-gender-reveal party, Jimmy gets "absolutely snozzled". Level 4 "Jimmy Drunk" is him being extremely sad and sentimental, leading into a slightly incoherent but very cute statement about Gretchen just as she's about to leave the party.Jimmy: I'm used to being the complicated one. Like with Becca. Becca's like a Monday crossword. Gretchen... Sunday. Takes all day, but so worth it.
- Another one at the end of "The Heart is a Dumb Dumb."Gretchen: You said something to me that was pretty dark.
Jimmy: Don't tell me.
Gretchen: Okay. I won't. [beat] I love you too.
- In "Try Real Hard", when Jimmy admits he's not comfortable saying "I love you" because he associates it with a promise/verbal contract that he's not ready to make. Gretchen's response doesn't sound all that comforting out of context, but it's perfect for them.Gretchen: If "I love you" is a promise, it's just a promise to, like, try real hard. Doesn't mean you can't fail.
Jimmy: It... doesn't?
Gretchen: Have you met me?! The only way I can stomach any of this is knowing I can bail at any time.
Jimmy: We can just... bail.
Gretchen: Yeah. I always have one foot out the door, in everything. Especially with us.
Jimmy: So you could just bounce.
Gretchen: Any minute.
Jimmy: ... I love you.
- "Twenty-Two": After the downright tearjerking way the episode (A Day in the Limelight episode for Edgar struggling to get through his day without medication to help his PTSD) had gone, there's the ending, where Edgar encounters another former veteran who gives Edgar some practical advice for how to help himself as he can't and shouldn't wait for anyone else to do that for him, as well as the student filmmakers getting Edgar to play the main character in their little silent film project.
- "No Longer Just Us" has Jimmy creating a fake local murder story to pique Gretchen's morbid curiosity, which was all a setup for him to propose to her. His abrupt exit afterward kind of dampens the mood, though.
- "Fog of War, Bro": For all of their loudmouthed chastising of her, Sam and Shitstain show they do care for Gretchen at the end of the day when she tells them about how Jimmy left her on that hill and how it screwed her up. They hug her and then call Jimmy out for his horrible actions.
- "It's Always Been This Way": After spending the day hanging out and getting ready to say their goodbyes before heading their separate ways, Jimmy realizes he can't make the same mistake again. He bursts into Boone's house and shows that he's willing to fight for Gretchen. He really steps up to the plate and deeply apologizes to her for abandoning her on that hilltop, admitting his issues and that he truly does love her and she deserves to be loved. This moves Gretchen to ultimately choose him. Sure, part of her choice is also based on the fact that she knows she has the power to destroy him (as does he, for that matter), but it just proves they belong together..
- It was looking rough for a while, but "Pancakes" turned out to be full of them. After 5 seasons together, numerous breakdowns, and bailing on their own wedding, Jimmy and Gretchen stay together with a relationship that works for them. Every day from now on, they'll choose to love or not love each other. And as we see in the epilogue, they have a daughter, having chosen to love each other every day for years.
- Throughout the fifth season, we're treated to ominous flashforwards into the future, indicating the worst will come to pass. These consist of: Jimmy selling the house with a somber look on his face, Gretchen checking into a hotel alone, and later agreeing to a drink with a random guy she meets, Jimmy picking up the florist he cheated on Gretchen with and driving away, and Edgar running for dear life. No matter how the wedding goes, things look bleak indeed... Nope, every single one of them is a Red Herring. Jimmy and Gretchen are moving to a safer house for children, leaving Gretchen to stay in a hotel for a while (and prove she can still get a guy's number), the florist is their nurse and Edgar's just playing with their daughter, Felicity, at Paul and Lindsay's second wedding. Turns out it was just an ordinary day in their lives.
Heartwarming / You're the Worst