I actually prefer “Made For Each Other”, which is on YouTube, but kind of an unknown gem, while many know “Annie Hall”, which is just as great.
Are you looking for recommendations of similar films?
There’s more than one “Made for Each Other”
Highly-educated protagonists who overthink their way into and out of a romance? Try Cameron Crowe’s SINGLES (1992). Shlubby-but-likable protagonist who pursues a woman who’s out of his league? KNOCKED UP (2007). What exactly are the distinctive elements of ANNIE HALL that you like so much?
Or just see other movies in which the couple get together, but in the end they don’t stay together. For instance, there’s Play It Again, Sam, which is my favorite film ever.
I once decided to call such films “anti-romantic comedies”, although that’s not a perfect name, I admit. Woody Allen was playing off of Casablanca in that film. That’s another movie in which the main couple get together but don’t stay together, although it’s not a comedy. Love does not triumph over all in such films. Another example is Shakespeare in Love. Tell us more about what you want in a movie.
The Sterile Cuckoo is a good movie for this theme, with an upbeat Liza Minelli whose underlying loneliness is heartbreaking toward the end.
Plus it’s got a wonderful theme song.
I loved the Bogart alter-ego (or conscious).