Kissing Jessica Stein Movie Review

Filled with situational comedic anecdotes revolving around the currently popular quandary of same-sex romances (a la Jeffrey, Trick, and Go Fish), Kissing Jessica Stein is a trite and conventional 90 minutes of fluff imbued with sappy lessons about faith and following one’s dreams.

In the latest iteration of the gay romantic comedy genre, Kissing Jessica Stein explores the world of bisexuality and centers on the various topics of telling your Jewish mother that you enjoy the taste of women and how to mix three shades of lipstick properly to the land the perfect girl.

Jessica Stein (Jennifer Westfeldt) is a middle-class and neurotic twentysomething Jewish girl, a strange mix of Lisa Kudrow’s character Phoebe from Friends and Woody Allen circa the 1970s, stuck with major insecurity issues concerning the opposite sex and her abilities as an artist. After a number of disastrous dates, including one with the infamous JM J. Bullock of Hollywood Squares fame, Ms. Stein gives up… until a quote in a women-seeking-women ad in a local rag perks her interest.

On the other end of the ad is Helen Cooper (Heather Juergensen), a woman with too many men bugging her for late-night booty calls. Helen wants honesty, compassion, and integrity – all elements that seem to be nonexistent in her recent selection of male partners. With the persuasion of a very cute gay male couple, Helen decides her only choice for happiness must then lie in the arms of a supple female.

After the novelty of two straight women deciding the do the mystery mambo wears off, the audience is treated to a silly documentation of two straight women swinging for the fences of sexual intimacy. But it's little beyond your typical high-school-movie-date with the nerdy girl who jumps at the slightest brush of another’s hand. Most of the remaining scenes are simply sitcom-esque constructions (family sleepovers, Jewish dinner rituals) built to inject humor but really just dragging things down further. The straw that broke this critic's back is the insulting subplot of Jessica’s former lover Josh (Scott Cohen), who serves as the obvious safety net when Jessica's experiment goes awry.

Aside from decent acting from a virtually unknown group of performers, Kissing Jessica Stein has nothing to redeem it. It's a trite and forgettable comedic parable, starring stock characters captured by a shaky handheld camera… and when it isn't focused on the leads, we get enough establishing shots of Manhattan to make the Woodman puke.

The Jessica DVD features a boatload of extras, including about 30 minutes of outtakes and deleted scenes (all with commentary from the starlets), not to mention two full feature-length commentaries (one from cast, one from crew). It's enough schmaltz to make you totally sick.

Who wouldn't kiss her?