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.