If Lucy Fell (1996)

Synopsis
This vanity project from writer, director, and star Eric Schaeffer is a romantic comedy about a pair of New Yorkers with a suicide pact. Joe MacGonaughgill (Schaeffer) is a painter and teacher who has been spying for years on Jane (Elle MacPherson), the gorgeous woman who lives across the alley, where she can be secretly observed undressing. Joe lives with Lucy Ackerman (Sarah Jessica Parker), a psychotherapist who's also his best friend. Suffering from her own relationship troubles with her boyfriend Dick (William Sage), Lucy is reminded of a long-ago pact she made with Joe: if neither is involved in a serious relationship by her rapidly approaching 30th birthday, they will commit suicide by jumping together off the Brooklyn Bridge. Then Jane comes to a show of Joe's artwork and he musters up the courage to ask her out, while Lucy begins dating Bwick Elias (Ben Stiller), an oddball artist who paints with his body parts. Only after Jane and Bwick turn out to be major disappointments do Joe and Lucy realize that they're perfect together -- and not in the platonic sense. Struggling independent filmmaker Schaeffer convinced Parker to take the female lead in If Lucy Fell when she hailed the cab he was driving. ~ Karl Williams, All Movie Guide