Film / Kissing Jessica Stein

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
  • Big Applesauce
  • Bittersweet Ending: Jessica and Helen break up, but they remain friends, and it's implied that Jessica gets back together with Josh.
  • Camp Gay: Helen's co-workers include a gay couple who are very camp.
  • Deadpan Snarker: Meyers is like this, mostly due to bitterness caused by past events.
  • 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: "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.
  • Jewish Mother: Jessica's mother is a textbook example.
  • Jewish and Nerdy
  • 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.
  • 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.
  • 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.
  • 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.