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Film / Kissing Jessica Stein

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Kissing Jessica Stein is a 2001 Romantic Comedy film about a Jewish woman named Jessica (Jennifer Westfeldt) whose life is changed when she meets a bisexual woman named Helen (Heather Juergensen). It was written by its stars and directed by Charles Herman-Wurmfeld.


Kissing Jessica Stein provides examples of:

  • Anguished Declaration of Love: Josh delivers one to Jessica right before kissing her.
  • Big Applesauce: The film's setting takes place in New York.
  • Bittersweet Ending: Jessica and Helen break up, but they remain friends, and it's implied that Jessica gets back together with Josh.
  • Bi the Way: Helen, who dates both guys and girls.
  • Camp Gay: Helen's co-workers include a gay couple who are very camp.
  • Closet Key: Helen for Jessica.
  • Deadpan Snarker: Meyers is like this, mostly due to bitterness caused by past events.
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  • Depraved Bisexual: Helen is a minor example. "Who do you have to blow to get some fucking pussy around here?"
  • Did You Just Have Sex?: After she has been with Helen for a few months, Jessica comes to work practically dancing. Immediately one of her friends asks Jessica whether she's been seeing someone.
  • Exact Words: Jessica to Josh when he asks if she's seeing a new guy. "Trust me. There is no guy."
  • Girl-on-Girl Is Hot: It is lampshaded in a hilarious scene. What makes it hilarious? Helen stroking Jessica's thigh under the table, and the fact that the guys to whom they are talking are completely oblivious to it.
    • The taxi cab honking loudly as it drives past the scene where Helen kisses Jessica can be seen as this.
  • Jewish Mother: Jessica's mother is a textbook example.
  • Jewish and Nerdy: Jessica.
  • Ironic Echo: Early in the movie, Helen says that she does not get sick, and Jessica repeats it to her when Helen is in bed with a cold.
  • Lipstick Lesbian: Jessica and Helen.
  • Love Triangle: Josh/Jessica/Helen.
  • Naughty Under the Table: Two guys who try to chat up Helen and Jessica at the bar, join them at a table and they start discussing sex. The guys say they love the idea of lesbian couples. Helen asks them what men find so fascinating about lesbians and lesbian couples, so the guys expound on their philosophy awkwardly and at length. Meanwhile, the scene is intercut with a view under the table of Helen feeling up Jessica's thigh. This naturally causes still-very-shy-at-this-point Jessica to squirm in her seat (uncrossing her legs and recrossing them in Helen's direction) and desperately try to not make a sound, while trying and failing to ask Helen just what she thinks she's playing at. Until Helen's hand disappears under the bottom of Jessica's dress, at which point Jessica can't help but give a sudden gasp of arousal. This is passed off as a leg cramp by Jessica, and Helen makes excuses of "You don't look well, I should get you home and into bed", and they leave to make love at Helen's place immediately. Just after getting through the front door however, they're interrupted by Helen's ex-boyfriend.
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  • No Bisexuals: This seems to be the attitude of the characters. The word "bisexual" is never used. Two characters even argue about how you can't just "switch" back and forth.
    Helen: It's just like kissing a guy.
    Joan: No, it's not!
    Helen: No, it's not.
  • Post-Kiss Catatonia: Jessica goes through this:
    Helen: So you know how you'll react to anything?
    Jessica: Pretty much, yes.
    (Helen kisses Jessica and watches her become stunned and silent)
  • "The Reason You Suck" Speech: Josh gives Jessica a truly brutal one in front of her friends.
  • Terrible Interviewees Montage: Jessica encounters "Malaprops Guy", "Weird Smooth Guy", "Calculator Guy", and "Not-Yet-Out-Gay Guy" (as per the credits).
  • Romantic Two-Girl Friendship: Jessica and Helen's relationship ultimately turns out to be this.
  • Transparent Closet: Jessica finally finds the courage to tell her mother about Helen, only the mother knows already and approves of Helen.


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