Oh. Very interesting question, anon.
I think for a large part of the finale, Nick projects his biggest fears and insecurities about himself on Jess. And then when he point blank asks Jess if she’s scared he’s too much of a mess, she says yes, thus confirming what he thought all along - that he’s not good enough and that they could never work.
That’s why he tries to push her away towards the end. He tells her she’s probably right about her fears (after all, they’re his fears, too). Then he deliberately plays their relationship down, says it’s not like they’re in love or anything. He tries to make it hurt less for both of them. Except they’re only hurting more.
I think Winston made him realize one crucial thing: he doesn’t need to act the way everyone expects him to, including himself. He doesn’t have to run away, that’s not all he is. He’s more and he needs to take action.
When Jess finally tells him that she doesn’t wanna give up on him and begs him to “un-call it”, I think that’s when he finally understands that yes, Jess might think he’s a mess and yes, she’s scared that that’s gonna get in their way, but it doesn’t matter to her. His flaws don’t matter to her, she wants to be with him because of who he is. She doesn’t want him to change. You can see the relief on his face after he realizes that.
One other thing: IMO, Nick didn’t try to change for Jess (like Schmidt implied). While Nick is certainly open to doing silly things, he certainly would never do anything to hurt someone close to him in the process. He said it himself: “How could you think I would do this at your best friend’s wedding?” Well, he wouldn’t have done that to her in season 1, either. He would never have embarrassed Jess like that, under no circumstances. Couple or no couple.
To sum up: I think Nick realized that maybe the circumstances don’t have to be ideal in order for him and Jess to try and maybe even succeed. And he now knows that Jess doesn’t expect anything of him aside from him being himself.
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