Kissing Jessica Stein is a 2001 American independent romantic comedy film, written and co-produced by the film's stars, Jennifer Westfeldt and Heather Juergensen. The film also stars Tovah Feldshuh and is directed by Charles Herman-Wurmfeld. It is one of the earlier film appearances of actors Jon Hamm and Michael Showalter. The film is based on a scene from the 1997 off-Broadway play by Westfeldt and Juergensen called Lipschtick.

Jennifer Westfeldt is an American actress, screenwriter, and producer. She is best known for co-writing, co-producing, and starring in the 2002 indie film Kissing Jessica Stein, for which she received an Independent Spirit Award nomination for Best First Screenplay and a Golden Satellite Award for Best Actress - Comedy or Musical. She is also known for writing, producing, starring in, and making her directorial debut in the 2012 indie film, Friends with Kids, which was included on New York Magazine's Top Ten Movies of 2012 list, as well as NPR's Top 12 of 2012.