Do you think that Nancy would have been happier in Boston if Jonathan had gone with her?
Honestly? Not really. Boston was never feasible, not the way it was introduced or pushed; it was always kind of a fantasy, even the way they talk about it. It always represented greater conflict to me.
Jonathan would not have been happy in Boston--at least not the way the show went about it--and so I think that would have put strain on the relationship, just like he worries about. Maybe if Jonathan is in a better place and in a position to pursue his own goals by her side, on even footing, things are fine. Especially with the Nancy we see in S4, confident in her goals and sure of herself. But even aside from being away from Jonathan, Nancy seems to be in an abysmal place emotionally by the end of the series, and who can blame her? It was going to be a very difficult period of her life no matter what.
Boston, by that point, becomes a way to hide, to run away from her problems. I know, I know, "independence", "real world", sure, fine, whatever. But that's still a kind of bubble, you know? And throwing herself to the wolves all alone and making things as hard as possible just feels like she's punishing herself and ignoring what she just went through. She's not running toward a future she wants but away from a past that has devastated and taken so much from her. She's trying to prove something. With Jonathan there, she has someone who understands and knows, but she tends toward insularity, you know? She has an ally and clings fiercely to that and doesn't necessarily branch out; she just pushes forward. So maybe he's a tempering force for that instinct, or maybe he's not; I can see an argument to be made either way.
Anyway, my greater point is that Boston represented a life that Nancy isn't sure she wants anymore and Jonathan's tendency toward self-abnegation. It never represented growth or happiness, and Jonathan still wouldn't have been happy because as much as he loves Nancy, he can't shape his whole life around her goals; that's not healthy or sustainable for either of them. And the reality of that dream isn't compatible with the place Nancy finds herself emotionally by then. Too much has changed. Jonathan's presence might have made it bearable, or he might have helped her see she was unhappy and make a change, or maybe it's a Band-Aid.
