Best I've seen in the subgenre are Kicking And Screaming & Metropolitan.
The latest winner I've found is 5 years old and completely off all major reviewers' radar. It's so off radar, despite the fact that it won the Best Screenplay award at the Los Angeles Independent Film Festival. How does this happen?!? What determines what films get widely reviewed? Kathy, Alan?
Strangely enough, I concur completely with the only user review at imdb:
When I saw the description and cast list for this movie, I didn't hold out much hope as to its quality. I expected either some ridiculous Zalman King -esque soft-porn thing or the cinematic equivalent of a sitcom. I was pleased to discover that I was wrong; this is a well-made, entertaining movie with engaging characters and great dialogue. The film focuses on the rather complicated romances of seven people living in an unnamed university town. All of the characters are interesting, but I was most fascinated by the neurotic, talkative Amy, played very convincingly by the charismatic Carla Gugino. On the whole, I found this to be a very clever, enjoyable film.What are your favorite character/dialogue films in approximately this subgenre? "Approximately", I say! Let's stretch it at least to include these passion-searching gems: Dream For An Insomniac, Splendor, and SubUrbia.