Kissing Jessica Stein (2001) is one of my favorite romantic comedies. It stars Jennifer Westfeldt and Heather Juergensen (who both also wrote this movie based on their play Lipschtick), and Scott Cohen and Tovah Feldshuh. It was directed by Charles Herman-Wurmfeld.
Jessica Stein (Westfeldt) is a neurotic, hopelessly single, 28-year-old, Jewish professional who works as a copy writer for a newspaper. She used to be an artist, but never felt that her paintings were good enough for her impossibly high standards, and neither are the men she keeps meeting. Her boss, Josh Meyer (Cohen), was Jessica‘s brother’s best friend in college and he dated Jessica for a year. He had dreams of becoming a writer, but fear of failing forced him into a life of mediocrity at the newspaper. Now, he’s just bitter, and tortured, because he’s still in love with Jessica, but, he doesn’t know it yet. Helen Cooper (Juergensen) is a free-spirit with a voracious appetite for sex, with men. She works at an art gallery with her two best male friends, a hysterical gay couple. Helen is unsatisfied with all the meaningless sex she’s been having with men, so she decides to try a woman. And, with the help of her friends, she places an ad, containing a quote from the poet Rilke, in the paper looking for woman. Now, Rilke happens to be Jessica Stein‘s favorite poet, and, having never met anyone who shared her same interests, she, on a whim, responds to Helen‘s ad. And, so, these two women, who’ve never been with other women, find that love isn’t just to be shared just between a man and a woman.
Kissing Jessica Stein is an amazing and beautifully heartfelt movie, and, I loved it when I first saw it back when it was released on DVD. The performances are brilliant, especially Scott Cohen as Josh. I love the scene where, at a dinner party, he tells Jessica what her problem really is, that maybe it’s not the men she’s dating but the impossibly high standards she sets for everything in her life. It’s a great scene, and well-written.
Another great scene is the heartfelt talk Jessica‘s mother (Feldshuh) has with her. Jessica is afraid to tell her family that she’s in a relationship with a woman, and they know Helen only as her friend. Her mother confronts her and tells this beautiful story about when Jessica was little and her high standards. She tells her that everything doesn’t have to be perfect if it’s something she loves. Then, she looks at Jessica, and begins to say something, but her voice cracks, she pauses, almost shedding a tear, then says, “Helen seems very nice,” and you know that she knows and that she accepts their relationship. It’s a brilliantly tender moment, and, very well done by Feldshuh.
Best line: Jessica keeps postponing their initial intimate moment, so, sex-hungry Helen complains to her gay friends, and says, in frustration: “Who do you have to blow to get some pussy around here?!”
Jessica is intrigued by Helen because she used the word “marinate” in a sentence that wasn’t about food. That’s funny because recently a friend used the word “co-sign” in regards to someone sharing the same opinion as me, and now I want to use that all the time!
Anyway, in the end, Jessica, due to Helen‘s influence, gets back into painting, and Helen displays her art at a showing. Josh shows up and is so taken by her work, that he becomes inspired, too. He goes home and begins writing through the night. He realizes then that the only person he wants to share his excitement with is Jessica, but, sadly, he learns that she’s with Helen.
Kissing Jessica Stein, apparently, caused some controversy in the lesbian community when it was released. Some argued that it wasn’t about real lesbians. Well, that’s true. It’s not. Jessica and Helen are not lesbians. Each, for different reasons, has had difficulty finding love in a straight relationship, and, each thinks that they’ll find what they’re looking for in a gay relationship. However, what they find is that gay relationships are just as difficult as straight relationships. The truth is that we’re all the same, gay or straight. We’re human.
Anyway, watch the trailer here: