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. Plot 28-year-old Jessica Stein is an attractive, Jewish, neurotic copy editor at a New York City newspaper. Her brother Dan has just gotten engaged, her best friend Joan is about to start a family, and her mother Judy is worried that Jessica will end up alone. Having endured several awful blind dates searching for Mr. Right, Jessica's interest is piqued by a personal ad that includes her favorite quote about relationships by Rilke. Jessica discovers it is in the "Women Seeking Women" section of the newspaper. The ad was placed by Helen Cooper, who works at an art gallery. Dissatisfied with unfulfilling sex with men, Helen is looking to try something different and decides to experiment with dating women at the encouragement of her gay friends. Jessica replies to the ad, but she becomes apprehensive when she meets Helen, then apologizes and exits. Helen chases after her and persuades her to stay for one drink. The two discover they get along well and have a lot in common; they have dinner. Helen challenges Jessica's assumptions about what will make her happy and passionately kisses her goodnight. Jessica and Helen start dating and awkwardly make out on Helen's sofa afterwards. The usually uptight Jessica gradually becomes more happy, confident, and carefree; this is noticed at her workplace and attracts interest from her boss, Josh. Jessica evasively says that she has not found a boyfriend. Helen, meanwhile, is falling in love with Jessica and grows frustrated that their relationship is not moving faster. Judy invites Jessica and Helen to dinner at their holiday house, where she tries to set them each up with a computer executive and Josh, respectively. A thunderstorm causes Helen to sleep over in Jessica's old bed, where she and Jessica have sex for the first time. The two of them are happy together, but Jessica stays closeted about her new relationship, refusing to bring Helen as her date to Dan's wedding for fear of what others will think. Devastated, Helen