''Kissing Jessica Stein'' is a 2001 RomanticComedy 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:
* AnguishedDeclarationOfLove
* BigApplesauce
* BittersweetEnding: [[spoiler:Jessica and Helen break up, but they remain friends, and it's implied that Jessica gets back together with Josh]].
* CampGay: Helen's co-workers include a gay couple who are very camp.
* DeadpanSnarker: Meyers is like this, mostly due to bitterness caused by past events.
* DepravedBisexual: Helen is a minor example. ''"Who do you have to blow to get some fucking pussy around here?"''
* DidYouJustHaveSex: 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.
* ExactWords: "Trust me. There is no guy."
* GirlOnGirlIsHot: It is lampshaded in a hilarious scene. What makes it hilarious? [[spoiler:Helen stroking Jessica's thigh under the table, and the fact that the guys to whom they are talking are completely oblivious to it.]]
* JewishMother: Jessica's mother is a textbook example.
* JewishAndNerdy
* IronicEcho: 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.
* NaughtyUnderTheTable: 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.
* NoBisexuals: 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.
* PostKissCatatonia: 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'')
* TheReasonYouSuckSpeech: Josh gives Jessica a truly brutal one in front of her friends.
* TerribleIntervieweesMontage: Jessica encounters "Malaprops Guy", "Weird Smooth Guy", "Calculator Guy", and "Not-Yet-Out-Gay Guy" (as per the credits).
* RomanticTwoGirlFriendship: [[spoiler:Jessica and Helen's relationship ultimately turns out to be this]].