Hav Plenty (1998)

A romantic comedy about a super-broke would-be novelist and sometimes homeless person who has been living on the streets of New York and off his friends while waiting for his fate to change. One of those friends is the beautiful, wealthy Havilland Savage, who invites Lee to a small gathering at her family's Washington D.C. home for New Year's Eve. Lee finds himself readily accepted and in several cases pursued by the rest of Hav's friends and family: Hav's high maintenance, high-octane best friend Caroline, Hav's newlywed and still uncertain sister Leigh, Hav's old prep-school pal Bobby, and Hav's mysteriously prescient grandmother. Lee journeys through it all not wanting anything, except to leave. Or does he? What if Lee were to own up to the fact that he wants Hav? Would Hav have him, if he has less than plenty?