Kissing Jessica Stein (2002)
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as Jessica Stein
as Helen Cooper
as Judy Stein
as Josh Myers
as Grandma Esther
as Sidney Stein
as Dan Stein
as Rachel, Dan's Fiancee
as Malaprops Guy
as Weird Smooth Guy
as Calculator Guy
as Not-Yet-Out Gay Guy
as Schuller Gallery Artist
as Seductive Woman At Gallery
as Josh's Date
as Cheesy Pick-up Guy No.1
as Cheesy Pick-up Guy No. 2
as Cab Driver
as Cab Driver
as Grandma Interrogating Helen
as Bookstore Saleswoman
as Helen's New Girlfriend
Critic Reviews for Kissing Jessica Stein
The cast is wonderful and the story is commendably free of the sectarian us-versus-them tone of many romantic gay movies.
Director Charles Herman-Wurmfeld's movie knows what it wants, what its limits are, and delivers its delights accordingly.
Westfeldt and Juergensen's wordy script tries for both mainstream and offbeat, but gets lost in between.
Westfeldt and Juergensen are both appealing actresses.
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  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.
Just a really inspirational movie. It's all worth it for the single scene where Helen is sick.
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.
Kissing Jessica Stein Quotes
|Judy Stein:||And you came home after the first day of rehearsal and said to me, "Mommy, I'm not gonna do it. I quit." And I said, "Jessie, my love, why?" And you said, "Because my co-star isn't good enough. And if my co-star isn't good enough, then the play won't be good enough. And I don't want to be part of any play that isn't good enough." And I thought to myself, oy. This child will suffer.|
|Judy Stein:||And you came home after the first day of rehearsal and said to me, 'Mommy, I'm not gonna do it. I quit.' And I said, 'Jessie, my love, why?' And you said, 'Because my co-star isn't good enough. And if my co-star isn't good enough, then the play won't be good enough. And I don't want to be part of any play that isn't good enough.' And I thought to myself, oy. This child will suffer.|
|Helen Cooper:||What'd you do to be happy?|
|Jessica Stein:||Nothing. I'm not.|
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