Taglines: When it comes to love, sometimes she just can’t think straight.
Jessica Stein (Jennifer Westfeldt) is a 28-year-old sensitive, but neurotic, New York journalist who is at the end of her emotional rope. Her brother Dan (David Aaron Baker), is engaged. Her best friend and co-worker Joan (Jackie Hoffman) is pregnant. On top of that, Jessica hasn’t dated in a year, and she can’t sleep. After an optimistic but nightmarish dating spree, which Jessica was inspired to set up by her overbearing and meddlesome mother Judy (Tovah Feldshuh), Jessica decides she needs a change in her life.
Helen Cooper (Heather Juergensen) is a 30-something, fairly successful art gallery manager who is fed up with having quicky sex with various men, including her delivery guy, in various times and places. Confused about her sexual orientation, as if she thinks she may be a lesbian in denial, Helen puts a personal ad in a local newspaper asking for a date with someone.
The following day, Jessica happens to read the intriguing personal ad, whose only drawback is that it’s in the women seeking women section. On a daring whim, Jessica decides to answer it. She meets the hipster Helen at a local bar for drinks and, to her surprise, they click instantly. After going for an evening of banter, connection and heated debate about Jessica’s personal life and her desire for happiness, the discussion culminates in a kiss that Helen gives which confounds and intrigues the reluctant Jessica.
Over the next few weeks, the two women proceed to muddle through an earnest, but hilarious courtship, making up the rules as they go along with private make-out sessions to casual dates to the local cinema. Jessica doesn’t really know how to think through this new situation. Meanwhile, everyone at Jessica’s office notices that she is walking on cloud nine and is very happy. Josh Myers (Scott Cohen), her boss (whom she dated for a while in college) also notices and starts to feel strange that he’s not a part of this new, happier Jessica.
On another dinner date, Jessica and Helen go out, they nearly get picked up by two sleazy guys at a local bar, and then proceed to return to Helen’s apartment for another make-out session, which gets interupted by one of Helen’s boyfriends. Helen asks him to leave, but after he does so, Helen comes down with a mild cold which puts off her and Jessica’s further make-out session.
One weekend, Jessica is invited to her mother’s country house on Long Island and she takes Helen with her to help her face off against her mother, and thus cancels hers and Helen’s plans to go to a hotel. After having dinner, Jessica then proceeds to consummate her romance with Helen that very night in her bedroom.
Some months later. A happy and improved Jessica flaunts her happiness in and out of the office, as her romance with Helen kicks into full swing. But Helen becomes more frustrated that Jessica wants to keep their romance a secret at any cost. One day, a very pregnant Jackie runs into Jessica and Helen while food shopping, and after catching Jessica in a lie about her and Helen, Jackie becomes privy to Jessica’s romance with Helen.
Kissing Jessica Stein (2002)
Directed by: Charles Herman-Wurmfeld
Starring: Jennifer Westfeldt, Heather Juergensen, Tovah Feldshuh, Esther Wurmfeld, Jennifer Carta, Jackie Hoffman, David Aaron Baker, Christopher Berger, Scott Cohen
Screenplay by: Heather Juergensen, Jennifer Westfeldt
Production Design by: Charlotte Bourke
Cinematography by: Lawrence Sher
Film Editing by: Kristy Jacobs Maslin, Greg Tillman
Costume Design by: Melissa Bruning
Art Direction by: Tema L. Staig
Music by: Marcelo Zarvos
MPAA Rating: R for sexual content and language.
Distributed by: Fox Searchlight Pictures
Release Date: March 13, 2002
Visits: 128
