Movie – Kissing Jessica Stein (2001)

The movie Kissing Jessica Stein asks the question, “Can a bi-curious, bohemian, arty woman and a neurotic, uptight, straight woman find love with each other in today’s world?”  The answer may or may not be “yes”, but either way it’s going to be a bumpy ride.  The film is a romantic comedy with some dramatic elements.  It features two appealing performances from the lead actresses, who also co-wrote the film.

Jennifer Westfeldt (Jessica Stein) and Heather Juergensen (Helen Cooper) decided that since they couldn’t get any great roles in other people’s productions they should write their own.  They first did a play titled Lipschtick and this ended up becoming the movie Kissing Jessica Stein.  At the time the film came out the two were celebrated as a female version of Ben Affleck and Matt Damon, who had famously done the same thing with Good Will Hunting.

While there was no mainstream Academy Award win for the two women, this film did win awards all across the Independent movie spectrum (GLAAD Media Award, Glitter Award, Los Angeles Film Festival, Louisville Jewish Film Festival, Miami Film Festival, Satellite Awards), as well as multiple Independent Spirit Award nominations.

In the film, Helen Cooper decides she is fed up with a string of quickie sex encounters with different men.  She decides she needs a change of pace and that the best way to accomplish that is to date a woman instead.  This pisses off her best friend, who is gay.  He feels that she is making light of who he is.  It’s done in a comedic way, though, so it doesn’t get preachy.  He eventually helps her craft the singles ad in the Women Seeking Women section of a newspaper.

Jessica Stein has not had a relationship in a year.  She is very frustrated with not being able to find anyone.  (Cue montage of bad dating experiences).  Her brother is getting married and this has brought out the worst in their mother (Tovah Feldshuh in a role written specifically for her).  Like pretty much every Jewish mother in a romantic comedy, every conversation she has with her daughter includes the question about when she is going to settle down and get married.

One of Jessica’s co-workers brings over the singles ad that Helen placed.  It has a quote by Jessica’s favorite author.  She’s intrigued, but then notices that it is in the Women Seeking Women section.  She tosses it out.  She can’t help thinking about it as the day goes on, and finally figuring what does she have to lose, she answers it.

Jessica and Helen meet at a hipster nightclub that Helen likes.  Needless to say, the buttoned down Jessica is out of her element.  Despite this the two of them click almost immediately.  The date ends with Helen surprising Jessica with a kiss.  Over the next few weeks they continue to date, with Jessica moving ever so slowly (waaaay too slowly for Helen’s liking) towards a relationship.

The uptight Jessica, who is never without a plan, decides the best thing to do is to research all about women being together.  She brings a bunch of books to their next date.  As she says to Helen, “I had no idea that lesbians had so many accessories” and she hands her a book.  Helen tries to convince her that they don’t need books; they should just do whatever feels comfortable.  Jessica finally agrees on a day when the two of them will “consummate” the relationship.

Things seem to keep interrupting them, though.  Jessica ends up bringing “her friend Helen” to her mother’s house for a weekend.  The mother, completely oblivious to any thought of her daughter being with another woman, has them sleep together in Jessica’s old room to allow other guests the bigger beds.  The room has been kept exactly like the teenage Jessica left it and Helen has a lot of fun looking through stuff.  When they go to bed both just lay there side by side very nervous.  Helen finally says, “I feel like if I try anything with you, your mother will ground me.”  Needless to say, they do finally take the next step.

Over the next several weeks Jessica is a lot happier.  Even her co-workers notice it.  One is her boss, who she dated several years ago.  This new Jessica suddenly is a lot more interesting to him than the old, uptight one.  While this is going on, Helen is frustrated that Jessica has not told anyone about their relationship.  Tensions start to run high between them.  Who will Jessica end up with?  The answer may surprise you.

A lot of humor is generated from the bringing together of the two very different women.  It’s literally an Odd Couple.  There are also a lot of laughs from the awkward little steps the two take towards becoming a couple. 

Here's your Don Draper ladies

Watch for a quick appearance by Westfeldt’s boyfriend Jon Hamm.  This was long before he was ever on Mad Men.  They had been dating for a few years so he flew in for a day to do a favor for her.  He had played Jessica’s boss in the original play.  He plays a blind date in the film.  By the way, the two are still together after 14 years.  Their relationship has lasted a lot longer than most Hollywood ones that involve two signatures on a piece of paper.  Also watch for Idina Menzel (Rent, Enchanted, Glee) in her first movie role as a bridesmaid.

Kissing Jessica Stein was quite successful, but unfortunately it didn’t translate into the kind of success for the two women that Good Will Hunting did for Affleck and Damon.  Both Westfeldt and Juergensen have worked regularly since, but they have not collaborated again.  Both have since written and directed their own movies – Juergensen with 2007’s The Suzy Prophecy and Westfeldt with 2012’s Friends With Kids.

Kissing Jessica Stein is a funny romantic comedy that may end up going in a direction that you do not expect.  Unless you find the concept offensive then I highly recommend this film.

Chip’s Rating: 4 out of 5 stars

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