30 Days of Pride: Kissing Jessica Stein

This is not the representation we deserve ladies and is offensive to the LGBT+ community. I am furious. For the second movie of pride month, I decided to watch Kissing Jessica Stein and it was a huge disappointment and a waste of my time.

Kissing Jessica Stein (2001) follows Jessica, a Jewish copy editor living and working in New York City as she struggles to find ‘The One’ in a pile of failed blind dates with men. As you do, she decides to answer a newspaper’s personal advertisement by lesbian curious Helen Cooper, an art gallerist. The film then follows their relationship and eventual demise because come on, no one is ever happy at the end of LGBT movies.

Kissing Jessica Stein is a romantic comedy that rarely made me laugh out loud and did not make me smile in the slightest. If anything, I was frowning by the end. An ending which was downright despicable. We’ll get to that though.

The first thing that is wrong with this film is how stereotypical it is. It is no wonder bisexuality has the reputation it has with the media representing it as it has here. That scene where Helen attempts to get close to Jessica by yawning and putting her arm over her shoulder…the classic heterosexual move was totally unnecessary. This film takes a lesbian couple and makes it fit the heterosexual norm. That guy that asks Helen if she’s twelve was me this entire movie. The girls put on squeakier voices, Helen is experimenting rather than actually being represented as a legitimate bisexual and overall portrays bisexuals as fickle and in the most crudest way a player who sleeps around.

As for the ending, of course early 2000s society couldn’t handle two women in a successful relationship. The ending sees Jessica return to a relationship with previous lover and colleague Josh Myers. Audience’s watch as she reunites with Helen to giggle like school kids over whether he likeeees her or not and do they have pooootential? No. It’s unfortunate the film concludes with some good ol’ hetero normalcy. To sum it up, a woman who has 0 compatibility with men falls in love with a woman only to go back to men at the end of the movie.

Jennifer Westfeldt as Jess gives a painful performance, probably highlighted more when alongside a bright and breezy Heather Juergensen (who is the only believable character in the whole film). Not smart. Not funny. Not fresh. Honestly, there were times during this movie where I wasn’t sure if they were deliberately stereotyping and being homophobic to make a point or whether the film makers genuinely believed that being gay was a lesser experience than being straight.