Kissing Jessica Stein

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 actor Jon Hamm. The film is based on a scene from the 1997 off-Broadway play by Westfeldt and Juergensen called Lipschtick.

Plot
Twenty-eight-year-old Jessica Stein is a copy editor at a New York paper. Her brother has just gotten engaged, her best friend Joan is about to start a family and her Jewish mother is worried that she will end up alone. Having endured a lot of awful blind dates searching for Mr Right, Jessica's interest is piqued by a personal ad in the paper from a woman seeking another woman for friendship and more, and which includes her favorite quote about relationships by Rilke. The ad was placed by Helen Cooper, who works at an Art gallery. Dissatisfied with casual sex with men, Helen is looking to try something different.

On a whim Jessica replies to the ad, but gets cold feet when they meet up, apologizes and rushes out. Helen chases after her and persuades her to stay for one drink. They find out that they have a lot in common, get along well and go for dinner. Helen challenges Jessica's assumptions about what will make her happy and then kisses her goodnight. The two start going out on dates and making out on the couch afterwards. This becomes frustrating for Helen who has fallen in love with Jessica and wants things to move faster. However, the usually uptight Jessica is now happy, confident and carefree. This is noticed at her work and attracts interest, especially from her boss Josh, but Jessica insists that she has not found a boyfriend.

Jessica's mother invites her and Helen to dinner at their holiday house, at which she tries to set them both up with an IBM executive and Josh respectively. Helen sleeps over in Jessica's old bed, and Jessica initiates the first time they have sex. The two of them are happy together, but when Jessica refuses to reveal their relationship to her family and friends, Helen says she can't accept this and leaves. Jessica goes to see her mother who tells her that she is a perfectionist who always quit things if they aren't just right and that she shouldn't let this ruin her chance at happiness with Helen, who seems like a nice girl. Jessica goes around to Helen's and invites her to be her date for her brother's wedding. Helen is a hit at the wedding and when Josh tells Jessica that he likes her, she explains that she has been seeing Helen and is very happy.

A few months later, Jessica and Helen are living together in an apartment. Helen starts an argument because they haven't had sex for a month. Jessica says she loves Helen, they are great friends & roommates, are intimate, and she's perfectly happy with that. Helen says that isn't enough for her, she wants passion and to be with someone who wants to tear her clothes off, so she breaks up with Jessica.

Later again, Helen is living with another woman. Jessica is putting up fliers to find a new roommate in a bookstore. She misses the flirtatious interest of the pretty store owner, but spots Josh, whom she has not seen since she left the paper to focus on her painting. They catch up and she tells him that Helen dumped her, which was tough. She gives Josh a flyer with her email on it. Later Jessica meets her friend Helen for coffee and tells her that she is going on a date with Josh.

Cast

 * Jennifer Westfeldt as Jessica Stein
 * Heather Juergensen as Helen Cooper
 * Scott Cohen as Josh Myers
 * Jackie Hoffman as Joan
 * Tovah Feldshuh as Judy Stein
 * Brian Stepanek as Peter
 * John Cariani as Chuck
 * Michael Mastro as Martin
 * Carson Elrod as Sebastian
 * David Aaron Baker as Dan Stein
 * Jon Hamm as Charles
 * Esther Wurmfeld as Grandma Esther
 * Michael Ealy as Greg
 * Michael Showalter as Stephen
 * Idina Menzel as Bridesmaid

Festival screenings
The film premiered at the Los Angeles Film Festival on April 21, 2001, receiving the Audience Award for Best Feature Film and a Critics' Special Jury Award.

The film was next shown at the Toronto International Film Festival, with screenings scheduled the day before and the day after the 9/11 attacks. According to the DVD commentary track by Westfeldt and Juergensen, both screenings took place, with the second screening on September 12 producing audible gasps among audience members at the sight of the World Trade Center. The two filmmakers decided to eliminate the nine or ten scenes featuring the Twin Towers because they weren't integral to the story, and distracted from it.

Critical reception
The film was hailed by critics upon release; it withstood some criticism from the LGBT community for not dealing in depth with the difficulties of being openly gay, but even among these criticisms, it was praised for portraying a same-sex relationship in a positive light. The website AfterEllen.com, which tracks the portrayal of lesbian and bisexual women in the media, reviewed the film positively. On Rotten Tomatoes, the film has an 83% "fresh" rating based on 120 reviews, with an average rating of 7.01/10.