After having several people recommend this movie to me, I finally decided to give it a try when I saw it on cable. I'm glad that I did, but I definitely found fault in some areas. The film is about Jessica Stein, a woman who is fed up with the dating scene and therefore decides to reluctantly approach a relationship with another woman, Heather, after reading her personal ad in the paper.

*Possible Spoilers*

This is another in a series of films where the characters are impossibly beautiful, smart and charming but cannot find anyone suitable to date. Admittedly, an excuse is made for Jessica in that she is a perfectionist and therefore cannot be happy until she `lets loose a little.' She also has an incredible apartment and the corresponding accoutrements that go along with having a fabulous existence in New York. I bring these material details up because they are just the beginning of several circumstances that just seem to happen too quickly and easily. The most glaring is when Jessica's mother just happens to know that she is dating a woman, and in the very next scene, Jessica's brother's wedding, suddenly the entire party is abuzz with this news and sitting around the table adoringly asking questions of `the lesbians'. Realizing that this is supposed to be a comedy, I tried not to look too deeply into this, but I felt about as put off by this display as I did by the entire film `Chasing Amy', only this time the lesbian was not `reformed' - it is hinted that Jessica may not indeed be a lesbian at all.

Having said these things, I did enjoy the film on some levels. I thought the acting was very natural and the dialogue was generally clever. I also think the filmmakers were right in not having a lot of character development because the basis of the movie was this one relationship, and therefore any expansion of supporting characters would have been unnecessary. I also like the evolution of Jessica's character, one who starts out like a 21st century Annie Hall and ends up being more comfortable in her own skin despite the fact that everything doesn't work out as one may expect. I found the ending to be very satisfactory because it cemented the conclusions that I came to earlier in the film - which is a welcome surprise because it usually does not end up that way for me; I am usually disappointed when things are wrapped up too neatly.

I know that this film was largely embraced by the gay community, and while I can understand that, despite its independent production, the relationship was very much `Hollywood-ized' in my opinion. However, having `marinated' the film, it is quite clear to me that it was not just about being a lesbian, but more in `finding oneself', as cliché as that term is. Overall, I consider it to be an enjoyable film as long as you do not turn too critical an eye to it.

--Shelly

At the beginning of "Kissing Jessica Stein" we meet Jessica (Jennifer Westfeldt) sitting in synagogue between her mother and grandmother discussing the lack of Jessica's love life. Jessica interrupts and says "Shut up mother, I'm atoning." This sums up and sets the tone for the greatness of this film - Jessica is authentic and very funny.

I connected instantly with Jessica as I am sure many single or recently single women can (and I'm not even Jewish). I usually hate making film comparisons to Woody Allen because a)its being done way too often and b)its just not Woody Allen who is still making great films for us. But in this case, part of my connection to Jessica is that writer and star Jennifer Westfeldt, like me, has probably seen "Annie Hall" one hundred times, and a great deal of Diane Keaton's Annie shines through in Jessica.

"Kissing Jessica Stein" is a romantic comedy about a girl who basically just doesn't know what she wants, but its better than that statement. The film is very well written and very funny. The relationships explored are real and three-dimensional and every element that moves the story forward is done with subtlety and humour. There is one mistake in the writing, and the writers make it obvious that they are writers, but it doesn't matter because the film is just that good. When they start getting too far from the audience with a character philosophizing about his current stance in life, they pull us right back in with a great line "You got dark." It also helps that Westfeldt is married to Jon Hamm and is friends with some of the best comedians in the business.

After you finish watching "Kissing Jessica Stein" (which, believe me, you have to),find Westfeldt's next foray into her version of romantic comedies "Ira and Abby" (2006). Oh, and if for some reason you haven't yet, see Woody Allen's "Annie Hall" (1977) first.

Jessica Stein (Jennifer Westfeldt) is a hopelessly single gal in the city. Her Jewish mother Judy (Tovah Feldshuh) is very concern. Everybody is getting married and moving on. She has nothing but bad dates. She thinks she's getting set up with Charles (Jon Hamm) but he's actually taken. At the group diner date, co-worker Josh Meyers (Scott Cohen) insults her with biting insights and cruelty. Helen Cooper (Heather Juergensen) is a bisexual art gallery assistant who places an intriguing personal ad. Jessica decides to answer it.

Westfeldt is playing the neurotic city girl. It's her goto move. It's cute. It's awkward. It has some fun. It's not particularly profound. It feels like a straight person's vision of a gay relationship. Everybody's life is different. I can buy into this relationship. It just pushes too hard with too many cute moments with cute awkward Westfeldt. It feels too light weight when the material keeps begging to be darker. It feels too much like a TV sitcom for too long.