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, and directed by Charles Herman-Wurmfeld. The film also stars Scott Cohen, Jackie Hoffman, and Tovah Feldshuh. 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 Lipschtick by Westfeldt and Juergensen. It was released in 2001 by Fox Searchlight Pictures.