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Kissing Jessica Stein (2001)

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A woman searching for the perfect man instead discovers the perfect woman.
8 wins & 3 nominations. See more awards »



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Cast overview, first billed only:
Esther Wurmfeld ...
Grandma Esther
Hillel Friedman ...
Ben Feldman ...
Robert Ari ...
Sidney Stein
Rachel - Dan's Fiancée
Nick Corley ...
Christopher Berger ...
Malaprops Guy


Jessica Stein is a single, straight, successful, journalist, part of a bonded Jewish family living in New York City, who finds herself not as straight as she thought when Jessica meets and begins an intense friendship with career woman Helen Cooper which ultimately leads to romance. Written by Anonymous

Plot Summary | Plot Synopsis


When it comes to love, sometimes she just can't think straight.


Comedy | Drama | Romance

Motion Picture Rating (MPAA)

Rated R for sexual content and language | See all certifications »

Parents Guide:





Release Date:

5 April 2002 (USA)  »

Also Known As:

Seeking Same  »

Filming Locations:



Box Office


$1,000,000 (estimated)

Opening Weekend USA:

$346,999, 17 March 2002, Limited Release

Gross USA:

$7,022,940, 7 July 2002
See more on IMDbPro »

Company Credits

Show more on  »

Technical Specs


Sound Mix:


Aspect Ratio:

1.85 : 1
See  »

Did You Know?


Future Broadway and Disney megastar Idina Menzel (RENT, Wicked, Frozen) has a small role in this movie. See more »


When Jessica and her mother are getting their bridesmaids dresses fitted, Helen is upset to learn that Jessica never mentioned her brother's upcoming wedding. But the wedding would surely have been discussed at the Shabbat dinner at the Steins' that Helen attended three months prior. See more »


[Josh is confronting Jessica after she made a private phone call]
Josh: You a little jumpy today Stein?
Jessica: No.
Josh: You got a hot date?
Jessica: No.
Josh: Yeah. Who's the guy?
Jessica: There's no guy.
Josh: Oh come on, you're a terrible, terrible liar.
Jessica: Trust me, there's no guy.
See more »

Crazy Credits

For our parents. See more »


Featured in Totally Gay! (2003) See more »


Devil May Care
Written by Bob Dorough & Terrell P. Kirk Jr.
Performed by Diana Krall
Courtesy of Sincere Music (BMI) all rights administered by Irving Music, Inc. (BMI) US and Canada; Rondor International administrates for the world excluding US and Canada and Verve Records
Through arrangement with Universal Film & TV Licensing
See more »

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User Reviews

"Kissing Jessica Stein" is the best kind of romantic comedy
22 June 2010 | by See all my reviews

At the beginning of "Kissing Jessica Stein" we meet Jessica (Jennifer Westfeldt) sitting in synagogue between her mother and grandmother discussing the lack of Jessica's love life. Jessica interrupts and says "Shut up mother, I'm atoning." This sums up and sets the tone for the greatness of this film - Jessica is authentic and very funny.

I connected instantly with Jessica as I am sure many single or recently single women can (and I'm not even Jewish). I usually hate making film comparisons to Woody Allen because a)its being done way too often and b)its just not Woody Allen who is still making great films for us. But in this case, part of my connection to Jessica is that writer and star Jennifer Westfeldt, like me, has probably seen "Annie Hall" one hundred times, and a great deal of Diane Keaton's Annie shines through in Jessica.

"Kissing Jessica Stein" is a romantic comedy about a girl who basically just doesn't know what she wants, but its better than that statement. The film is very well written and very funny. The relationships explored are real and three-dimensional and every element that moves the story forward is done with subtlety and humour. There is one mistake in the writing, and the writers make it obvious that they are writers, but it doesn't matter because the film is just that good. When they start getting too far from the audience with a character philosophizing about his current stance in life, they pull us right back in with a great line "You got dark." It also helps that Westfeldt is married to Jon Hamm and is friends with some of the best comedians in the business.

After you finish watching "Kissing Jessica Stein" (which, believe me, you have to), find Westfeldt's next foray into her version of romantic comedies "Ira and Abby" (2006). Oh, and if for some reason you haven't yet, see Woody Allen's "Annie Hall" (1977) first.

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