Very few romantic comedies are willing to step past the boundaries of traditional societal norms when it comes to the main relationship of the film. Kissing Jessica Stein is one of those great ones that recognizes the diversity of relationships that exist and embraces them wholeheartedly; it examines the advantages, disadvantages, consequences, and possible eventualities. Kissing Jessica Stein is an open-minded look into the world of culturally dubbed "alternate lifestyles". The plot is superb, the acting relatively above-par, and overall the movie plays well despite a few flaws.
Jessica Stein (Jennifer Westfeldt) is a girl with standards set too high and consequently single; her friends try to set her up but with the much expected failures she becomes frustrated and exasperated with even trying. Is there no hope for Jessica? Enter the newspaper personal ads. Helen Cooper (Heather Juergensen), one of the city's cultural and artistic elite, is looking for another woman to balance her out and commit to an eventual long-term relationship. At first Jessica is appalled at the idea of hooking up via personal ads under the impression that such things lead to nothing. Upon replying to Helen's ad, with great reluctance and secrecy, she sets up the first date and the movie moves on from there.
The ever-cautious and overly scrupulous Jessica must find a way to push through her sexual insecurities before losing the interest of Helen through frustration and exasperation. For every foot that Helen gains on the sexual front Jessica puts another one in its place; it's not that Jessica doesn't want it, it's just that she doesn't know if she can do it. On top of that, Jessica has kept her relationship (or at least the truth about her relationship) with Helen a complete secret from not only her ex-boyfriend Josh (Scott Cohen) and co-workers, but her own family (who has met her countless times without ever catching on) as well. All this secrecy has finally caught up with Jessica and Helen won't tolerate it anymore; Helen demands that their relationship be unveiled and that Jessica finally accept her feelings not only privately but publicly too.
Kissing Jessica Stein is a candid and very accurate portrayal of relationships and all their nitty-gritty details and for that we ought to applaud. The truths passed onto the general public through Kissing remind us that relationships are a universal factor of human life no matter what road you walk down. No matter what your lifestyle the fact of the matter is Kissing Jessica Stein will in some way mirror some of the emotions or thoughts that occur to all lovebirds.
Unfortunately universal truths aren't enough to completely salvage a movie. The acting is good at best. Some of the dialogue becomes stilted and stodgy in its deliverance and towards the end when they oh so bluntly deliver the "moral of the story" it starts to sound a little preachy; after awhile you never want to hear the universal truth ever again no matter what kind of relevance it may have.
Jennifer Westfeldt does well but her performance is nothing special. She goes in, plays the character, and gets out. There's no feeling that the character will stay with you. You may even be able to relate to Helen since Jessica is portrayed as a rich whiny girl who can't make up her mind. This act gets tiresome very fast. Heather Juergensen is the better side of the couple as her acting seems to fit better with the story and she tends to have some of the better lines during the one-on-one scenes with Jessica. Even though I said, Heather played the better act in the relationship that still doesn't make it a phenomenal performance in any way. Helen is also rather forced as a character and not much can be said for the complexity of the character.
Though maybe that's not the fault of the actresses. It could be said that as insightful as the movie is, it spends too much time on this insight and not enough on developing the characters themselves. We get so annoyed with Jessica and the movie never does enough to show us a side of her that redeems her from the land of the irritating. Helen also fails to leave the realm of the two-dimensional and simply plays her counterweight without ever really showing us some of the deeper sides of her artistic personality.
While romantic comedy fanatics will find this movie quite enjoyable, the majority will find it a bit slow. The choice is yours.
"Kissing Jessica Stein" opens March 13, 2002 and is rated R. Comedy, Romance. Directed by Charles Herman Wurmfeld. Written by Heather Juergensen and Jennifer Westfeldt. Starring Heather Juergensen, Jennifer Westfeldt, Tova Feldshuh.