With his solo directorial effort, "If Lucy Fell" (1996), Schaeffer attempted to reinvent the romantic comedy for the 1990s with his tale of two friends who have agreed to a suicide pact if neither has married by the time they are thirty. In addition to co-producing and acting in the film, which co-starred Sarah Jessica Parker (in a role prefiguring her "Sex and the City" character) and Elle Macpherson, he wrote a screenplay representing a quantum leap from his debut, but the picture met with a mixed reception at the box office, despite its more cohesive style and narrative. He fared even worse with "Fall" (1997), a sexually obsessive reworking of the beauty and the beast myth starring Schaeffer (again as a cab driver) opposite Amanda De Cadenet as a married fashion model. Largely dismissed by critics and ignored by audiences, the character study of two people trying to create and maintain a serious relationship displayed Schaeffer's gifted ear for dialogue, though De Cadenet's model came across as unsympathetic.During the late 90s, Schaeffer began turning up more frequently as an actor-for-hire. After essaying the part of Gwynne in "Gunshy" (1998, which premiered on Cinemax before its video release), he landed a regular role as the twice-divorced doctor son of Jeffrey Tambor and Jill Clayburgh in the short-lived NBC sitcom "Everything's Relative" (1999) and later starred in the DreamWorks-produced CBS sitcom pilot "Legal Aid" (lensed 1999), playing one of an assortment of lawyers in a NYC public defender's office. He returned as an actor-writer-director with "Wirey Spindell" (1999), a teen sex comedy for the grown-up art-house crowd that employed four actors to portray the titular character at different ages. Its story of a sexually preoccupied man on the eve of his marriage to a woman for whom he has lost his sexual desire was not without its rough spots, but Schaeffer's quirky view of life helped put the sexy film across. He then acted in Harold Zwart's "One Night at McCool's" (2001), which starred Michael Douglas, Matt Dillon and Liv Tyler.