Kissing Jessica Stein

A cute 28-year old professional in New York City can’t seem to find the “right guy” in her life. After several failed attempts at relationships, the neurotic woman decides to give her own sex a shot, and the next thing you know, she’s making out with another woman and liking it? Lesbianism, comedy and Jewish families…ensue.

A cutesy romantic tale with a twist, I found myself enjoying this film more and more as it went along, especially since I could relate to its lead character, who didn’t seem to be able to connect with that special someone and who was probably too “perfectionist” for her own good. That is until she ultimately decides to play tonsil hockey with the home team and sparks begin to re-appear in her life (mental note to myself). What I liked most about this movie was that it really managed to convey a real sense of…well, confusion in its lead character. Played softly by co-screenwriter Jennifer Westfeldt, Jessica came off as a real woman caught up in this real sense of desperation, with her ex-boyfriend shooting her down, her family giving her static and her friends all wanting to hook her up. The connection between her and her eventual “girlfriend”, Heather Juergensen, also worked (and it’s no wonder, Juergensen is the other screenwriter of this movie and they both starred in the play together before this), and it was nice to see both characters going through the same shite that most hetero couples go through as well (you mean…we’re all the same deep down inside??) Needless to say, the message behind the script, the pitfalls of their relationships as well as the joys, are all easily relatable by anyone in the heterosexual community. In fact, I thought the whole premise of this girl actually “trying” to become a lesbian was quite entertaining, in that quirky, perverted way (an alternative title for the film could have been: “How to Become a Lesbian”).

On the downside, the film didn’t necessarily break any new ground in the relationship department, other than the whole “gay” angle, and I really didn’t like how Jessica kept alternating her feelings about the whole “lesbian” thing so quickly (even three months into it, she’s still willing to drop it all because she feels that it’s “icky”-I don’t know). The last half hour of the film was probably where I got most interested as the fluffy comedic vibe to that point, was suddenly elevated to a more serious tone, with a handful of dramatic scenes coming through and bringing home some of the feelings behind the jokes. The scene between Jessica and her mother outside her house was particularly touching, as was Josh’s eventual confession. I also liked how they concluded things, although I could see how some in the gay community might see it as a “sell-out”, but for what it was in the context of the story, it made sense to me. Girl Confused / Girl Experiment / Girl Find Herself. The songs in the movie were also charming, as well as the beautiful shots of New York (a little Woody Allen shows up in most romantic comedies set in New York) and the montage scenario of Jessica’s unsuccessful dates was a gas. On the downside, I think the two gay men in the film were sadly over-caricaturized and Josh’s character, while eventually turning sympathetic and three-dimensional, started off as a complete heel and made a strange transition. Now even though many people who watch either/or “Friends”, “Sex in the City” or “Will & Grace” pretty regularly will likely shrug their shoulders at most of this stuff, there is enough in the film to make up for its sitcom feel, especially in the depth of its two lead characters and the ultimate message of the story. Now who’s gonna kiss me??

(c) 2021 Berge Garabedian