What can I say? Mrs. Salad looooves Kevin Kline. It's OK, because it usually works out, as here. This movie wasn't too popular with the critics or even the IMDB raters, but I found it slightly better than OK.
The primary character is Louis, played by Paul Dano. He sees himself as a character in a Fitzgerald novel—complete with a Nick Carraway-like narrator. He's also slightly confused about his sexuality, as he has an occasional compulsion to wear ladies' underthings. This doesn't go over well at the prep school where's he's teaching, so he sets out for Manhattan where things are somewhat looser. By chance he answers a roommate ad from Henry Harrison, Kline's character. Henry is outspoken and (seemingly) full of tall tales about his past glories. His current primary profession seems to be the escorting of elderly rich women to social events. But he's at the edge of destitution: if an occasion calls for him to wear black socks, he resorts to coloring his ankles with black shoe polish. And (of course) Louis gets caught up in all this; one funny sequence involves them sneaking into the opera.
I'm pretty fond of screwball comedies, but this is more of an oddball comedy. The humor, as such, involves the interaction between eccentricities. It worked for me, although a lot of air goes out of the goings-on when Kevin Kline is absent.