Ahem…this is going to be controversial. But what follows is a brief list of romantic comedies and dramas in which the “wrong choice” love interest is far more deserving than the “right choice” one.
Perhaps the originator of this trope, Elsa was right to stay with Victor, but Rick is Rick, and you know she’ll always wonder.
The Sound of Music (1965)
What can I say except McSweeney’s convinced me: Captain Von Trapp would have been happy married to Baroness Schrader.
Pretty in Pink (1986)
Let me say I think the “she should have ended up with Duckie” stuff is overplayed (see Jon Cryer thoughtfully arguing against that here), but I don’t think there’s any doubt Duckie is a better realized character than Blane. I’ve always wondered if twenty years later, Duckie and Andie might make a go of it.
You’ve Got Mail (1998)
I always pretend this movie is centered on Patricia (Parker Posey) and that after her boyfriend (Tom Hanks) dumps her to pursue the children’s bookstore owner (Meg Ryan) whose business he destroyed, Patricia goes on to take over New York publishing and find love with someone worthy of her.
At the level of satire, this movie works for me. At the level of romance…no, definitely not. Idina Menzel’s Nancy in particular deserves much better than she gets. The idea that driven career women secretly want to become princesses? No, not so much.
Letters to Juliet (2010)
This film could make the list twice, first because the B-plot (the romance between Vanessa Redgrave and Franco Nero) is infinitely more interesting and charming than the A-plot, but also because Gael Garcia Bernal is a metric ton more attractive/beguiling than Christopher Egan.
ETA: I deliberately omitted Twilight not wanting to reopen Edward vs. Jacob…but yeah, Team Jacob. All the way.