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). To her surprise (since before she only dated men), Jessica falls for Helen. They begin dating, but the relationship becomes difficult as a result of Jessica wanting to keep it a secret from everyone. It was written by its stars and directed by Charles Herman-Wurmfeld.
Kissing Jessica Stein provides examples of:
- Alcohol-Induced Bisexuality: This is the final straw that ends Jessica's sexual relationship with Helen, who notes that Jessica never seems open to having sex with her when she's sober.
- Anguished Declaration of Love: Josh delivers one to Jessica right before kissing her.
- Bad Liar: Jessica is a terrible liar, and Helen sees through it instantly when she tries, saying it's one of her best qualities.
- 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.
- Camp Gay: Helen's co-workers include a gay couple who are very camp.
- Closet Gay: Jessica, who dates Helen in secret and struggles to keep her bisexuality hidden from others.
- Closet Key: Jessica realizes she's attracted to women by meeting (later dating) Helen.
- Coming-Out Story: After a kiss with Helen, Jessica struggles to come out to her mother as bisexual (she does tell a friend, who finds it surprising but is excitedly approving). Fortunately, her mother knows and approves.
- Deadpan Snarker: Meyers is like this, mostly due to bitterness caused by past events.
- 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 guys they talk with say it's because one woman may be sexy, but two is double sexy.
- The taxi cab honking loudly as it drives past the scene where Helen kisses Jessica can be seen as this.
- Grammar Nazi: Jessica finds it a deal-breaker with one date that the guy lacked proper diction.
- Jewish Mother: Jessica's mother is a textbook example. She's very emotional, nags her adult kids to do what she feels is best and pushes for "good matches" with other people whether they want these or not (often annoying them).
- Jewish and Nerdy: Jessica, who's a neurotic Grammar Nazi, instantly recognizes a quote from Rilke and is Jewish.
- 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 (lipstick bisexuals actually). They dress and act femme, with a plot point being that both love lipstick (discussing what kind is good).
- Lying by Omission: When Jessica's mother asks why she's so happy lately, Jessica replies that there's no boy involved. She's actually dating 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.
- 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.
- Open-Minded Parent: Jessica's Jewish mother, who tries to fix Jessica up with a nice guy, surprisingly supports her daughter after she comes out to her.
- 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)
- Really Gets Around: Before dating Jessica, Helen casually mentions she was having sex with three men at once (but breaks off those arrangements for her).
- "The Reason You Suck" Speech: Josh gives Jessica a truly brutal one in front of her friends.
- Secret Relationship: What Jessica tries to have with Helen, keeping their affection with each other from the public. Helen finds this increasingly annoying, and eventually insists on them being public about it, with Jessica acceding.
- "Shaggy Dog" Story: The whole movie is about Jessica breaking out of a string of relationships with the wrong man and discovering her own bisexuality through a relationship with Helen. The movie ends with their happy relationship eventually breaking down to the point that they split up and Jessica then hooks up with the nice guy who's been doggedly chasing her for the entire length of the movie. For anyone expecting a bisexual girl-girl romance flick, the ending makes the movie come off as this trope.
- Stalking is Love: Jessica ends up with Josh who quite obsessively went through her personal files (including letters) at work. Apparently, because he was motivated by jealousy from their past relationship, this is fine.
- Terrible Interviewees Montage: Jessica encounters "Malaprops Guy", "Weird Smooth Guy", "Calculator Guy", and "Not-Yet-Out-Gay Guy" (as per the credits).
- Too Much Information: Helen says this after her gay friends briefly discuss their sex life in front of her.
- Transparent Closet: Jessica finally finds the courage to tell her mother about Helen, only the mother knows already and approves of Helen.
