2024 Entry #011 01-07-24 “Kissing Jessica Stein” is a 2001 American independent romantic comedy film, written and co-produced by the film’s stars, Jennifer Westfeldt and Heather Juergensen; directed by Charles Herman-Wurmfeld (“Fanci’s Persuasion”, “Legally Blonde 2: Red, White & Blonde”, . The film also features openly gay John Edward Cariani (“The Good Wife”), Ben Weber (“Sex and the City”, “The Broken Hearts Club: A Romantic Comedy”) Tovah Feldshuh (“Friends & Family”, “Ugly Betty”, “The Good Wife”), Scott Cohen (“Oz”, “Gia”), Jackie Hoffman (“Queer Duck: The Movie”, “The New Normal”, “The Good Wife”, “Glass Onion: A Knives Out Mystery”), Brian Stepanek (“Six Feet Under”, “Green Book”), Jon Hamm (“Ally McBeal”, “Mad Men”, “A Single Man”, “Howl”, “Absolutely Fabulous: The Movie”, “Mean Girls”) & Michael Showalter (“Wet Hot American Summer”). The film is based on a scene from the 1997 off-Broadway play by Westfeldt and Juergensen called “Lipschtick”.
The story follows the title character, a Jewish copy editor living and working in New York City, who is plagued by failed blind dates with men, and decides to answer a newspaper’s personal advertisement, placed by a thirtysomething art gallerist, a ‘lesbian-curious’ woman. I had seen this movie once before, when I purchased it for my collection, when it was relatively new – so close to 22 years ago. Of that viewing, I remembered a powerful scene between Jessica (Jennifer Westfeldt) and her mother Judy (Tovah Feldshuh) on a swing, in which Judy reveals that she is supportive of Jessica’s relationship with Helen (Heather Juergensen), the gallerist; I cried both times that I saw it. The other scene I remembered was the breakup between the two women and the reasons for it. Otherwise, I remembered nothing; not even that it was set in NYC.
This movie is a bit of a mixed bag for me. I enjoy it, but I could have loved it and I didn’t. I think there are a few really successful ideas here about relationships and what constitutes a healthy one; how people can inspire us to be better than we were before – and can simply inspire us to do our best, our most creative work, which isn’t the same thing. But I think the tone of this piece is a little too “safe” and is so hellbent on being fluffy and fun that it often does a disservice to the strength of these messages. And I think that this silly romantic comedy occasionally gets out of its own way and allows for depth and honesty.
And then there’s the other problem, which may be more problematic for some than others: I’m not certain there are any lesbian characters in this supposedly lesbian themed film. I think if the film stood its ground more often and didn’t pull its punches this would be less annoying, because there is something to be said for the experiences of women who have relationships with women beyond lesbianism, but because it plays everything as frothy and weightless, that subject matter is presented as nearly devoid of anything of worth, and it didn’t have to be that way. But because of that, I wish the film had just allowed these characters to be lesbians. A fun lesbian comedy would be both easier to convey and a more welcome story to discover, as finding lesbian films which actually feature lesbian characters, who aren’t there only for decoration or flavor seems to be shockingly rare. Though I do give the movie some props for one of the bisexual women ending up with a woman, as her ending up with a man would have been so obnoxious as to spoil the film altogether.
Overall, this IS a silly romantic comedy, but every now and again there is something of greater value to be found here, which suggests this story could have been something much better.