Culture Magazine

Movie Review – Kissing Jessica Stein (2001)

By Manofyesterday

Director: Charles Herman-Wurmfeld

Stars: Jennifer Westfeldt, Heather Juergensen, Scott Cohen, Jackie Hoffman

Jessica (Westfeldt) is a successful journalist but unsuccessful in her romantic life. Filled with quirks and hang-ups, she enters a new world when she finds herself involved with the owner of an art gallery, Helen, but this new relationship is fraught with uncertainty as she hides the true nature of her affection from everyone she knows.

People have different opinions about fluid sexuality. It’s not always handled with the most care in films, but in this one the lesbianism isn’t played gratuitously and the relationship does feel like a genuine one. The two people involved are different in many ways. Helen is a free spirit and has a string of lovers that satisfy different needs, while Jennifer is continually shooting people down for sometimes shallow reasons.

And this contrast is at the heart of the film. As their relationship develops Helen gets more frustrated with Jennifer, and the central message of the story is that sometimes it’s not enough to find someone else to fix you. Jennifer is constantly unable to accept certain parts of her personality, and because of this she isn’t capable of having a stable relationship. I’ve been single for a while as well, and I recognized a lot of the frustrations of the dating world, but knowing yourself before getting into a relationship is definitely something that’s good advice.

The film moves along briskly although the last part feels crammed with changes that could have been dealt out more gradually, but overall I enjoyed it. The actors were likeable and it’s a pretty decent film.


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