Stillman wrote the screenplay for "Metropolitan" between 1984 and 1988 while running an illustration agency in New York, and financed the film by selling the insider rights to his apartment (for $50,000) and with the contributions of friends and relatives. Loosely based on Stillman's Manhattan days, with his divorced mother during the week of Christmas break 1969 during his first year at Harvard, "Metropolitan" tells the story of the alienated Princetonian Tom Townsend's introduction to the "Sally Fowler Rat Pack" (SFRP), a small group of preppy, Upper East Side Manhattanites making the rounds at debutante balls during Christmas break of their first year in college. Though he is a socialist deeply skeptical of the SFRP's upper-class values, Tom (Edward Clements) grows increasingly attached to the cynical Nick (Chris Eigeman) and plays an important part, of which he is largely unaware, in the life of Audrey (Carolyn Farina), a young debutante. Many of the exclusive interior locations were lent to Stillman by family friends and relatives.