Template:Infobox Film Kissing Jessica Stein (2001) is a U.S. 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. The movie is based on a scene from the 1997 off-Broadway play by Westfeldt and Juergensen called Lipschtick.
Template:Spoiler Twenty-eight-year-old Jessica Stein (Westfeldt), a Jewish heterosexual copyeditor living and working in New York City, is plagued by failed blind dates with men, and decides to answer a newspaper's personal advertisement containing a quote from Rilke that she had read and admired earlier. The advertisement has been placed by 'lesbian-curious' Helen Cooper (Juergensen), a thirtysomething art gallerist who is dissatisfied by her meaningless sex with men.
Given some of the men Jessica is shown to be test-dating at the start of the film, ranging from borderline gay to nerd, some would probably say that it's no surprise she'd want to fan out her prospects a little. As nervous as Jessica is about dating Helen, she realizes after a surprise kiss that even a different experience can be good.
Through the early part of their relationship, Jessica finds in Helen everything she'd dreamed of finding in a man. They are compatible, they like many of the same things, and they are caring for one another. Even when Helen gets sick — which she says earlier in the film never happens to her — Jessica is there to care for her.
The only predicament for the relationship is Jessica's reluctance towards same-sex intimacy. Over the early weeks of their relationship, she and Helen slowly work on building up her confidence in this area by gradually extended make-out sessions. Eventually, they graduate to full intimacy, though Jessica is clearly uneasy about the same-gender sex.
In spite of Jessica's happiness with Helen, she keeps the relationship secret. Jessica's secrecy means that she has to endure scenes that would not happen had she been open about the two of them. One example occurs during a dinner to celebrate her brother's engagement. Her mother (Tovah Feldshuh) had invited an IBM executive in hopes of setting him up with Jessica.
Helen and Jessica later get into a quarrel about Jessica's refusal to inform her family of their relationship, resulting in an apparent breakup. It isn't until later, as her brother's wedding approaches, that her mother figures out that they are dating and lets Jessica know by simply saying Helen "seems like a nice girl."
This acceptance on her mother's part gives Jessica the confidence to come out in the open with her relationship with Helen, and invites her as her guest to her brother's wedding. Helen becomes an immediate curiosity of the other women at the reception. It is there that Jessica gets a kiss, this one from ex-beau and current boss Josh (Scott Cohen), who confesses that recently she has been the object of his fascination.
Jessica and Helen move in together, but their relationship, while good in all other ways, suffers from a lack of sexual intimacy. It becomes clear that Jessica is still uneasy with the sexual facet of the relationship and loves Helen as a friend, and not a lover. The relationship ends amidst Jessica's tears and Helen's realization that she wants more than Jessica is willing to offer. After moving beyond the heart-break, Helen and Jessica remain best friends, and Jessica starts to show renewed interest in Josh at the end of the film, after both have left the newspaper they both previously worked for. Template:Endspoiler
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 12th 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 served to distract from it because of the attacks.
Kissing Jessica Stein was hailed by critics upon release and was generally applauded for being suitable for heterosexuals and homosexuals alike. It withstood some criticism from the homosexual crowd for refraining from dealing in depth with the difficulties of homosexuality in a heterosexual society, but even among these criticisms, it was praised for portraying a same-sex relationship in a positive light. Rotten Tomatoes lists the movie's cumulative rating as an impressive 91%. 
- Kissing Jessica Stein at Fox Searchlight Pictures
- Kissing Jessica Stein at the Internet Movie Database
- Template:Metacritic film
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