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I wanted to but couldn't!

This is one of the few movies I've ever seen where the whole audience broke into spontaneous, loud applause a third of the way in.

It's the kind of movie you'll want to see a second time with someone who hasn't seen it yet, to remember what it was like to watch it for the first time.

I didn’t really have many expectations going into the movie (good or bad), but I actually really enjoyed it. I really liked the characters and the banter between them.

This movie is already over 15 years old and I am surprised I never saw it or heard about it because it was pretty good. It is about a woman that has no luck with men and answers an ad of another woman that she finds interesting. While being straight this starts to develop into a relationship.The acting in the movie is really good. The main characters also wrote it. Surprised not to see much acting on Heather Juergensen's IMDb as she was really good, but I guess she stayed in writing.And it is because of the writing that I liked the movie so much. The dialogues are great. I loved the argument they had when Jessica didn't invite Helen to brother's wedding. The talk Helen had with her gay friends. The conversation Jessica had with her mother. There was a lot of good writing.There are many small characters that are also a delight and adding a lot in the few scenes where they appear. I loved Grandma Esther, and this is the only acting credit of Esther Wurmfeld! Kevin Sussman also made me laugh a lot in his dating scene.The ending doesn't seem to be a typical happy ending but I loved them nonetheless. They break up because after all Jessica isn't gay and sex doesn't work. But they are best friends so this doesn't go away. Helen finds a woman to be happy with and Jessica meets Josh again and now that she found out more about herself and being happy it may even work out.A very creative and outstanding rom com.

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.

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.

This charming, lightweight comedy about sexual orientation and experimentation stars the adorable, funny Jennifer Westfeldt as a good Jewish girl who decides that maybe the whole heterosexual dating thing isn't working for her, so she's going to play for the other team for a while. She begins a timid "romance" with a girl in much the same boat, with the exception that Westfeldt never really takes to lesbianism and the other girl does. Though the lesson she learns -- the problem in connecting with men lies in her own inability to sustain an intimate connection with another human being, not in any hidden homosexual tendencies -- is obvious, it's well told, and the director manages to keep the film from seeming glib or trendy. Westfeldt is a lovable actress, and she navigates the iffy terrain between cute and annoying very well.Grade: B+