Kissing Jessica Stein (2001)

movie_35784I was very fascinated by this when it came out back in early 2002, so when it finally came on, I was very anxious. What I got was a rather tender movie. This girl struggles with the dating scene and constantly experiences loser after loser in the first half with a hilarious sequence that shows her on many dates with these odd men, one of whom has her pay the entire bill for the dinner. Jessica Stein is a lonely girl who works at a newspaper. She’s constantly set-up by her mother with a lot of men, but the dates are never successful. Frustrated, she answers an alternative lifestyle personal ad in hopes of making friends with a girl.

Inadvertently, the girls helps her to explore the alternative lifestyle in which she’ll discover herself and her own happiness. Jessica, (Jennifer Westfeldt) is a very timid and meek character who is very likeable. She’s often giggling throughout the flick which makes her an enjoyable character. She does tend to lose all hope and explores lesbianism with a rather promiscuous man-eater Helen who is instantly flirting with Jessica throughout the movie. I thought she was a very interesting character symbolizing the complete opposite persona of Jessica’s character.

The movie has a lot of humorous moments, including one when the extremely tight knit Jessica, before having sex with Helen, makes her read a pamphlet about lesbian sex. Each of the lead characters are very funny and have great chemistry with each other keeping me interested all the way through. “Kissing Jessica Stein” unfortunately never truly knows what it wants to be. It tries to be a romance then a drama then a comedy but just drops flat on all spectrals. I thought Jessica, herself was not quite a truly likeable character and kind of annoyed me at times. I was very angry with the ending of this film.

In the end, Jessica, now fully set with her life, makes yet another decision and decides, she’s not lesbian after all. That was a complete let-down and utterly annoying. I thought the movie was good so far with the life-altering decision she makes throughout the film, but the climax tends to take all that happened from the previous and just flushes it down the drain. After watching the end a lot of people will feel that the entire movie was for nothing because of her decision. Mostly a flick that will translate towards the female audience, this is an enjoyable love story with great characters, but tends to fail in the climax, ruining the entire movie.