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Kissing Jessica Stein (A Movie Review)

Updated: May 13, 2020

Kissing Jessica Stein on Blu-ray

Kissing Jessica Stein on Blu-ray


Starring Jennifer Westfeldt, Heather Juergensen, Tovah Feldshuh, Scott Cohen, Jackie Hoffman Martin, Carson Elrod, David Aaron Baker, Tibor Feldman, Michael Showalter, Michael Ealy, Christopher Berger, Hayden Adams, Kevin Sussman, Jim J. Bullock, Idina Menzel and Jon Hamm.

Screenplay by Heather Juergensen and Jennifer Westfeldt.

Directed by Charles Herman-Wurmfeld.

Distributed by 20th Century Fox Home Entertainment.  94 minutes.  Rated PG-13.

It goes to show how much the world has changed in the twelve years since Kissing Jessica Stein was released to remember how edgy and different it was considered when it came out.

The idea of a romantic comedy in which a neurotic, totally straight heroine tires of a series of calamitous relationships with men and finds herself falling into an affair with an arty and wild bisexual woman seems almost tame now, but at the time it was rather scandalous.

However, the fact that it is the story of two women in love is not Kissing Jessica Stein’s biggest selling point, though it was undoubtedly the film’s calling card when it became a cult favorite at the time.

The fact of the matter is Kissing Jessica Stein is an abnormally good romantic comedy, no matter what the gender of the lead couple may have been.  This is not just a good lesbian love story, this is a good love story, period.

Kissing Jessica Stein was written by its two stars, Jennifer Westfeldt and Heather Juergensen, and was based on their play Lipschtick.  (Thankfully they changed that puntastically awful title for the film version, or no one would have ever seen it.)

Westfeldt has since gone on to write and direct the good-but-overlooked 2012 film Friends With Kids, was nominated for a Tony for the play Wonderful Town in 2004 and has starred in TV series like Notes From the Underbelly and an arc on Grey’s Anatomy.  She is also well-known as Mad Men star Jon Hamm’s longtime live-in lover.  (And yes, a then mostly-unknown Hamm does show up here in a small role as a dream fix-up date who turns out to be not quite as unattached as their mutual friends had thought.)

Juergensen, on the other hand, has pretty much disappeared since this role.  Well, okay, she was the romantic lead in Adam Carolla’s straight-to-video indie boxing film The Hammer, had a relatively big role in Simon Tamar Hoffs’ barely-seen Red Roses & Petrol and had a very small part in the 2003 film version of the Disneyland ride The Haunted Mansion.

On the evidence of Kissing Jessica Stein, both should have had even more success over the years.

Westfeldt plays the title character, an uptight but charming magazine copy-editor who had moved to the big city New York after a well-off childhood in the tony suburb Scarsdale.  Despite the fact that her mother (the always wonderful Tovah Feldshuh) is constantly trying to fix her up, Jessica hasn’t had a real serious relationship since college.  That was with Josh (Scott Cohen), who is now her boss and whose near constant snipes may or may not hide deeper feelings.

One day, on a whim, she decides to answer a personal ad in the “Women Seeking Women” section of their magazine, entirely because it used a favorite quote of hers by poet Rainer Maria Rilke.

Through the ad, she meets Helen (Juergensen), a completely comfortable in her skin manager of an art gallery.  Helen isn’t lesbian either, she’s an adventurous and easily bored bisexual who has always tended more towards men – in fact she is juggling four of them when she meets Jessica – but is looking for a change of pace.

Jessica has second thoughts, but they become friends and slowly feelings start to emerge.  This brings up a whole set of complications, including family, friends and work.  Of course, they are both hip New York women, so it’s not shocking they’d have been a bit ahead of the curve.

Whether they end up together for the long haul is hardly the point.  The ups and downs of the relationship – and how much it is like every relationship at the same time as it is wonderfully unique to itself – this is what turns this little romance into a quirky, sweet treat.

And it is nice to note that twelve years down the line, the sexuality of the characters feels like an afterthought.

Jay S. Jacobs

Copyright ©2014 All rights reserved. Posted: June 14, 2014.

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