Kissing Jessica Stein (2002)



Critic Consensus: A trite but refreshing and comical spin on nature of love.

Movie Info

A woman searching for the perfect man instead discovers the perfect woman in this romantic comedy. Jessica Stein (Jennifer Westfeldt) is a woman with a solid career as a copy editor, but her love life isn't much to write home about; she's been through a long series of disastrous first dates that refuse to evolve into second dates, and the well-intended advice of her best friend Joan (Jackie Hoffman) and former boyfriend Josh (Scott Cohen) isn't helping a bit. One day, Jessica is scanning … More

Rating: R (for sexual content and language)
Genre: Comedy, Romance
Directed By: ,
Written By: Heather Juergensen, Jennifer Westfeldt
In Theaters:
On DVD: Sep 17, 2002
Box Office: $7.0M
Fox Searchlight Pictures - Official Site


as Jessica Stein

as Helen Cooper

as Judy Stein

as Josh Myers

as Grandma Esther

as Sebastian

as Himself

as Sidney Stein

as Dan Stein

as Rachel, Dan's Fiance...

as Larry

as Malaprops Guy

as Weird Smooth Guy

as Calculator Guy

as Not-Yet-Out Gay Guy

as Schuller Gallery Art...

as Seductive Woman At G...

as Charles

as Josh's Date

as Cheesy Pick-up Guy N...

as Cheesy Pick-up Guy N...

as Cab Driver

as Cab Driver

as Stanley

as Bridesmaid

as Grandma Interrogatin...

as Bookstore Saleswoman

as Helen's New Girlfrie...
Show More Cast

News & Interviews for Kissing Jessica Stein

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Critic Reviews for Kissing Jessica Stein

All Critics (123) | Top Critics (32)

The cast is wonderful and the story is commendably free of the sectarian us-versus-them tone of many romantic gay movies.

Full Review… | February 3, 2009
Chicago Reader
Top Critic

Director Charles Herman-Wurmfeld's movie knows what it wants, what its limits are, and delivers its delights accordingly.

Full Review… | August 18, 2008
Top Critic

Pure pleasure.

Full Review… | July 25, 2008
Top Critic

Westfeldt and Juergensen's wordy script tries for both mainstream and offbeat, but gets lost in between.

Full Review… | February 9, 2006
Time Out
Top Critic

Westfeldt and Juergensen are both appealing actresses.

Full Review… | July 21, 2005
Houston Chronicle
Top Critic

Venturesome yet unthreatening, this movie is box-office smart enough to seem cutting-edge without ever drawing blood.

Full Review… | November 5, 2002
Atlanta Journal-Constitution
Top Critic

Audience Reviews for Kissing Jessica Stein


I have a girl crush on Jennifer Westfeldt (which seems appropriate for this movie about a buttoned-up Jewess trying on lesbianism to find her [7] true love[s]). Too bad she's all in a committed long-term relationship with hunk-o-man Jon Hamm.

Westfeldt as Jessica is so adorably neurotic and girl-next-door-pretty. My perennial favorite, Scott Cohen, is mean and tough but also sweetly anguished. Jessica and Helen's romance blossoms awkwardly and hilariously at first, but the moment Jessica comes over to take care of Helen when she's sick is a nice turning point. The movie debates homosexual politics a bit, but it doesn't end with a clear message about whether one should be with her own sex or the other. It also doesn't cheapen Jessica's lesbian relationship as a dalliance.

I also love how the script sneaks in bunches of word-nerd humor and suffering artist philosophy. Judy's monologue about how Jessica quitting the school play because she thought her costar wasn't good enough - and only really hurting herself - is a metaphor for her dating life is eloquent and insightful. Josh's realization at his happiness for Jessica's painting and his own novel writing is a necessary reminder for all creative artists. Blech.

Alice Shen

Super Reviewer


Just a really inspirational movie. It's all worth it for the single scene where Helen is sick.

Letitia Lew
Letitia Lew

Super Reviewer

I thought this movie was supposed to be more of a comedy (just my perception, not a misleading trailer as often happens). So I got over that easily and enjoyed it.

Megan S

Super Reviewer

Kissing Jessica Stein Quotes

– Submitted by Letitia L (3 years ago)
– Submitted by Catherine M (3 years ago)

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