After a brief unsuccessful stint at the University of South Florida, Boosler worked as doorman at The Improvisation comedy club in New York for three years, and it was there that she met comedian Andy Kaufman, a regular at the club, who convinced her she should do standup comedy. The two dated for three years and remained friends until Kaufman's death. Boosler credits Kaufman for her "comedy education" as well as her other peers at the time which included Freddie Prinze, Jay Leno, Larry David, Richard Lewis, Richard Belzer, Jimmie Walker and Ed Bluestone.