Kissing Jessica Stein
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“You’re not getting any younger, you know.”

“You should meet my cousin Larry. You’d be perfect for each other.”

“Maybe you’re just too picky.”

Every single woman, at some time in the course of her single-girl-hood, has most likely heard one (or all) of those lines.

Repeatedly.

Jessica Stein (Jennifer Westfeldt) definitely has. She’s a twenty-eight-year-old New York copy editor—and an artist on the side. Everyone around her is either engaged or pregnant. She’s been on an endless stream of horrible dates with all the wrong men. And her mother is becoming very vocal about her fears that Jessica will be single forever.

Meanwhile, in another part of New York City, Helen Cooper (Heather Juergensen), an art gallery director, is tired of the way her life is going. Sure, she’s got a man for every occasion, but none of them really make her happy. So she decides that her friends’ alternative lifestyle might work for her, too, so she puts out an ad in a local paper—in search of another woman.

  
 
After being set up with a great guy who’s already in a relationship, Jessica stumbles upon Helen’s ad and talks herself into giving this girl thing a shot. But no matter how well she and Helen get along, Jessica is embarrassed, nervous, and neurotic—but she’s also the happiest she’s been in ages. Her friends and family start begging to meet this new guy—and her boss/ex-boyfriend starts to get jealous. But Jessica has no intention of telling everyone that this wonderful new guy’s name is Helen.

I’m not going to beat around the bush here. This is quite possibly the best movie I’ve seen in a long time. I mean, really. Let’s face it. How many of you, somewhere in the course of singlehood, ever joked about altogether giving up on men and switching to women? I know I did. Kissing Jessica Stein just takes that one step further.

But this isn’t just a girl-meets-girl movie. It’s a movie about discovering who you really are. Sure, it’s about love and friendship, but, more importantly, it’s also about figuring out who you really are—and doing what makes you happy (even if it’s a little unconventional and risky). And not only is it inspirational and all that deep and meaningful stuff, but it’s light and funny, too. Though Jessica annoyed me a bit with her extreme neuroses and wishy-washy-ness, I have to admit that her nervousness was a major source of humor in the movie. I laughed almost to the point of tears when, on her second date with Helen, she arrived with a collection of books and pamphlets about lesbianism to peruse and discuss.

Kissing Jessica Stein is an excellent movie for any woman who’s ever woken up and decided that she wasn’t happy with her life—and that she needed to make a change. And if you’re one of those women (and really—who isn’t?) who’s gone on one too many bad dates, you’ll like it, too. Give yourself a manicure, get yourself a pint chocolate ice cream and a spoon, and watch this movie—you deserve it.

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