Before tonight, I have never even heard of this movie. I also don't normally watch romantic comedies because many times, they are very corny and just don't work. Now, while this movie isn't perfect (and believe me, it is VERY far from perfect), it is interesting in both premise and title.Kissing Jessica Stein actually starts off on a promising note. While the 2 love interests (Jessica and Helen) have very different beginnings, their chemistry as a couple is really believable. Because of that, I am on board for a lesbian love story. Throughout the movie, I kept rooting for their relationship to grow and for a while, it does. Jessica and Helen I think are a really cute couple and when they're in love, they are very likable as characters. As Jessica and Helen make out, it gives a sexy vibe to the movie.But, giving this indie film a chance, my praise ends as I leave that last paragraph. See, this film could have been much more, but instead, we get a totally watered-down, rushed plot that is really just a cöcktease and past the make outs, the film never really goes anywhere and instead plays it safe. In a film about lesbian relationships, it would have been a better move to show a few scenes of nudity since it stated the 2 girls have sex, and as an indie film about a lesbian relationship, this probably would have benefited more as an NC-17 film rather than an R.The transitioning is so fast that it becomes haphazard really quick. As a result, the plot has no flesh, no development, and many times throughout the movie, I am left wondering what happened. It isn't all like this because obviously the heart-to- heart Jessica and her mother have has time to be in the movie, but many scenes (a make up scene between Jessica and Helen is most definitely one of those scenes) could have used a few more minutes time given to the scene so that I could understand the happenings of the film a little more.Speaking of which, the ending where Jessica and Helen break up for good and become just friends really defeats the purpose of the film and so it squanders a chance to really be something special. Once again, how this all happens is rushed to oblivion and it really doesn't work. It would have done better to let the 2 girls grow in love with one another and end in their own wedding. Instead, it becomes a clichéd guy gets a girl ending that just doesn't fit in at all.One last thing, the soundtrack is atrocious. Good songs are ruined by bad covers, and the songs I haven't heard before ruin the mood of the movie. The only thing these songs add to anything about the movie is how safe this movie plays.So with everything said, I welcome gay relationships in movies. Brokeback Mountain and Boys Don't Cry do this very well. But in the case of this movie, it could have been a great movie, yet it didn't want to take risks and instead went for a rushed, safe plot.

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.

That's the line uttered by a an unbearably obnoxious female (?) character who just discovered that her friend is a lesbian. I think that sums up what's wrong with this movie.Even more ridiculously, the friend says the sex is great, and the obnoxious supposedly-female character asks, "really?", to which the friend affirms.That was so implausible and so stupid, I was in tears of laughter. Because if I one day I discover that my best ostensibly-straight friend is gay, the first thing I'll ask is "Wow you're gay Bob? So how's the sex?" Bob: "Oh it's great!" Me: "Really?" Bob: "Oh yeah absolutely! You should come watch us some time! Man I'm so glad you're so cool about this!" The movie has its smart and funny moments, but come on, it jumped the shark right there.

The summary refers to the series of Broadway plays that the two stars Jennifer Westfeldt and Heather Juergensen created that spawned this movie. I bring it up because this unique story of love and sex between and among smart,attractive and neurotic New Yorkers has the feel of a collection of dialogs and vignettes. To some,that might be bothersome or boring,but not to me.The title character(Westfeldt)is an attractive magazine editor and aspiring painter in her late twenties. While she seems okay with herself,she's not okay with her love life. Between being fixed up on dates with successful but less-than-enthralling nice Jewish men by her well-meaning but somewhat intrusive mother(Tovah Feldshuh) and the lack of men who seem to "do it" for her. On a whim,she answers a personal ad in a New York paper,only this time the ad is from a woman. That woman,Helen(Juergensen) is almost everything Jessica isn't: fresh,open-minded,outwardly affectionate,completely satisfied with who she is and patient. The two totter through a handful of dates on the verge of "going all the way"(and one guess as to just who is holding back here!)before they finally take the plunge on a full physical relationship. And even though they are perfect for each other,Jessica still somehow cannot reconcile herself with this relationship and lifestyle which she mantras as being "not her".Directed by Charles Herman Wurmfeld as well as adapted by co-writers Westfeldt and Juergensen,this definitely has a Woody Allen sensibility to it,from the layer dialog and pathos-riddled characters to even the sly usage of music to context the NYC backdrop. Strong support is lent by the supporting cast,most notably Scott Cohen(as Jessica's acid-tongued ex and co-worker),Jackie Hoffman(as her closest friend at work),Feldshuh,Michael Maestro and Carson Elrod(as Helen's gay friends,who are both impressed and put off by her limbo-esquire bi-or-lesbian relationship). While the whole story and some of the characters may drive even someone who genuinely enjoyed the movie(like myself)to a sense of frustration,I still found this movie a pleasant romantic comedy alternative to what much of Hollywood(and,granted,I understand WHY Hollywood would be quite reluctant to try themes like this,but still...)sends out.