Sunday, September 27, 2020

Cinema Sunday: Kissing Jessica Stein


Today, Cinema Sunday takes a look at Kissing Jessica Stein, a 2001 romantic comedy film, written and co-produced by the film's stars, Jennifer Westfeldt and Heather Juergensen. 

We've covered the whole "experienced lesbian meets cute with a woman new to this whole lesbian thing" before but this film represents a bit of a change from those movies I've discussed here before. 

Kissing Jessica Stein is not set in the 1950s. 

And both women are new to this whole lesbian thing. Still, one is a bit more open to the idea and the other is very neurotic about it.  



The neurotic one is twenty-eight-year-old Jessica Stein, an attractive copy editor at a New York City newspaper. She is the prototype for literally hundreds if not thousands of hetero romantic comedies, the super busy career woman who wants to find love but damn it, she has standards and her career keeps her so super busy. 






Her brother Dan has just gotten engaged.

Her best friend Joan is pregnant. 

Her mother Judy is worried that Jessica will end up alone. 

Jessica's dating life is not giving us a lot of hope. A montage of some really awful dates shows the dating hell that Jessica is up against. (Including a really young, pre-Big Bang Theory Kevin Sussman.) 

Then Jessica's interest is piqued by a personal ad that includes her favorite quote about relationships.

The ad is in the "Women Seeking Women" section of the newspaper.

Jessica Stein answers the ad and meets Helen Cooper. 

Helen works at an art gallery. Dissatisfied with unfulfilling sex with men, Helen's gay friends encourage her to try dating women. 

Jessica shows up for the date but is very apprehensive. 

Helen persuades her not to leave and the two bond over drinks and dinner, discovering they get along well and have a lot in common. 

The first date ends when Helen passionately kisses Jessica goodnight.

Jessica and Helen start dating. Awkward make out sessions ensue.  Jessica brought manuals and catalogs which she thinks might help. Helen's not really sure they need manuals and all that equipment.   

Judy invites Helen to accompany Jessica home for dinner with the family. Forced to stay overnight because of a bad thunderstorm, Helen and Jessica sleep together in Jessica's old bed where they have sex for the first time.  

Jessica and Helen are happy together but Jessica is as neurotic as ever, keeping her new lesbian relationship a secret, fearing what others may think.  

Helen refuses to be treated as a shameful secret and breaks up with Jessica.  

With her brother's wedding approaching, Jessica is in a deep funk and goes to her mom. Judy tells her two very important things: 

1) Jessica is perfectionist who always quits things if they are not perfect, even if they make her happy. 

2) Jessica should not let this ruin her chances at happiness with Helen, who seems like "a lovely girl". 

Whoa! Mom knew about Jessica and Helen this whole time and she's OK with it? That is so cool! 

Jessica apologizes to Helen and invites her to be her date for Dan's wedding. Helen is a hit at the event and warmly welcomed into the family.

The end.

OK, no, sadly, not the end. 

A few months later, Jessica and Helen are living together in Helen's apartment and  their sexual relationship begins to fade. Helen realizes that Jessica views her as a best friend and roommate more than a lover. Jessica is OK with that but Helen needs more. After a bad fight, the two split up for good. 

More months go by and we find Helen is happily living with another woman. Jessica is a more calm and content version of her former self, having taken the positive things she learned from her time with Helen and applied them to her own life. She meets up with Josh, her editor at the paper; she has not seen him since she left to focus on her painting. 

Jessica meets up with Helen; the two women now solidly friends. Jessica tells Helen she is going on a date with Josh.


Kissing Jessica Stein got dinged by the LGBT community for not dealing in depth with the difficulties of being openly gay, but  was praised for portraying a same-sex relationship in a positive light. 

The Advocate magazine listed the film as an essential film for LGBT viewers, stating that "By no means is it a model lesbian movie — in fact, the film is a more honest look at bisexuality and sexual fluidity — but it is certainly a movie that encourages exploration and self-awareness."

Beyond the ground breaking same sex relationship, Kissing Jessica Stein also upends the tropes of romantic comedies. What usually happens is the featured couple goes through hell together but they will end up on the other side still together, happy and in love. This is not the fate for Jessica and Helen which is a shame but it is sadly realistic. Both women were in the rush of something new for both of them; unfortunately, relationships built on that kind of energy do not last as that kind of energy will change. 

Still, it is good that Jessica and Helen do end the movie still friends and better people for their experience. Nonetheless, it remains heart breaking when two have that big fight and break up for real. 

Kissing Jessica Stein is any many ways a standard take on the romantic comedy with the quirky, neurotic girl struggling to find love in the big city. It goes beyond that standard with a message of acceptance and challenging our expectations. 




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