A bit overrated, but still an amazing film

Instead, you get a movie that's enjoyable enough, but leaves you feeling like it could have been much, much more.

This is a must-see and one of the best documentaries - and films - of this year.

A great movie, one of the best of this year. There was a bit of confusion at one point in the plot, but nothing serious.

When I first saw this movie back in 2000 something, I was a confused 11 year old who just started noticing that I might be into other girls. It aired on late night TV one day, and I remember seeing the summary for the movie and feeling a sort of tense excitement at the thought there might be actual people like me represented in a movie. So I stayed up and watched the whole thing (way past my bedtime, too) and that experience has never quite left me. I'm still looking for my Helen to this day.The movie explores its subject matter in a clever and humorous way and doesn't feel overly cheesy, despite not differing much from your typical romcom other than the main characters' sexuality. Overall, very charming and worth watching if you're interested in LGBT cinema.

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.

KJS was directed by Charles Herman-Wurmfeld, but written by Heather Juergensen & Jennifer Westfeldt, who star in the film as New Yorkers Jessica Stein & Helen Cooper. Despite the lesbianism there is little T&A- the leads are rather frumpy, but not unattractive, women. The story is every lesbian's fantasy- seducing a clueless straight girl fed up with the male sex. This banal premise goes nowhere. Jessica's hetero-frustration is portrayed in a montage of bad dates that could only occur in films, so right away emotional realism is tossed, & sets the film up for a failure to connect on anything but a superficial level. Helen is a bisexual fed up with men's shallowness & places 1 of those 'bi-curious' personal ads. Jessica reads it, is intrigued by a quote from Rilke (she is a copy editor & bookworm), & answers. Even though the ad claims to seek 'friendship or more' any person over the age of 20 (especially a copy editor) would know this is adspeak for a lesbian relationship. The 30+ Jessica is clueless, & spends the whole film never even attempting to get with it. That Jessica, as portrayed before meeting Helen, could ever be attracted to such a duplicitous & shallow sort as Helen- even if a man- undercuts the whole point of her dates-from-hell montage. Also, it's supposed to be funny that she approaches her 1st lesbian experience with a slew of 'how to' books. Yes, this is a comedy, but it's not too much to ask the characters & writing to show some maturity & developmental stability.

Seeing the trailer, I really did not think this was going to be a favorite. I thought it's gonna be a feel-good flick about "coming out" or maybe "sexual identity confusion" which would eventually be another romantic I-saw-that-already. Though admittedly there were some clichés and bad acting left noticed, what caught me sticking was the intensity in most scenes and dialogues--delivered naturally and wickedly satirical and funny! Also, I think that the way the cinematography payed attention to the small details around a particular character is exquisite (e.g. like how Jessica, for all her intellect, still has a dumb side -- maybe because her facial features are quite of a blonde's? Well, she's a Jew so I don't know ^_^ )