“Kissing Jessica Stein” Is a Classic of Queer Jewish Anxiety

In Lost Movie Reviews From the Autostraddle Archives we revisit past lesbian, bisexual, and queer classics that we hadn’t reviewed before, but you shouldn’t miss. 

Shanah Tovah.

I hope those of you who celebrate had a relatively joyous Rosh Hashanah. And now please join me in the High Holy Day of revisiting Jewish queer woman classic Kissing Jessica Stein, directed by Charles Herman-Wurmfeld, written by Heather Juergensen and Jennifer Westfeldt, and starring Juergensen, Westfeldt, and legend of stage and screen Tovah Feldshuh.

I’ve often wondered the cause of so many Jewish clichés — the anxiety, the indecision, the exact way a Jewish mother can critique you with a compliment. I’ve wondered how widespread it is — how class, race, location, and sect impact these behaviors. I can’t generalize about an entire religion, but I can speak to my own experience. For me, Judaism is about questioning. I suppose some people turn to religion for answers, but I don’t see the appeal. I love the not knowing, the curiosity, the constant push to better understand ourselves and our world. It’s a lifelong journey and the only one I know. It can be really fucking miserable.

I think Jewish guilt is more about Jewish obligation, Jewish uncertainty. Sure, the Torah is a guide to living a meaningful life, but the further you get from taking it as a strict rulebook, the less clear its instructions become. It’s simple enough to say that helping others is a tenet of Judaism. But does this mean a life dedicated to activism? A commitment to Jewish community? A commitment to individual community? An obligation to family? If you try too hard to live for others, a meaningful life won’t have much meaning. You can become stuck in a state of anxiety, so desperate to do right that you do nothing at all.

To say that 2001 romcom Kissing Jessica Stein begins with these questions might seem silly except that it literally starts in a synagogue on Yom Kippur. Jessica is sitting between her grandma and her mom Judy and Judy is trying to matchmaker matchmaker make Jessica a match right in the middle of service. Is marrying a random man before you turn 30 to make your mom happy the key to a meaningful life? What about having the impossibly high standards of your grandmother? Jessica finally snaps. “Mom, would you shut up? I’m atoning!”

The fact is Jessica is trying to follow the path best suited for her family. She’s stopped painting except as a hobby — opting instead for a stable job at a newspaper. She goes on miserable date after miserable date desperate to get married and have kids and do everything she’s expected to do. But the thing about Jessica is she’s too smart or too stubborn or too something to ignore herself altogether. She simply cannot settle in love how she’s settled in her career. Something is pushing her to want more.

Enter Helen. Helen is not Jewish. Helen is not anxious. But Helen is also questioning. She takes out a woman-seeking-woman personal ad in the paper in pursuit of her first queer experience. When Jessica makes the out of character choice of responding to the ad — a Rilke quote will do that to you — Helen is totally smitten. Even as Jessica tries to flee the date and call it a mistake and make every excuse she can imagine, Helen waits patiently. This starts to seem like more than an experiment for her. This other woman feels worth the wait.

On their first date, Jessica makes a snide remark about a group of Hare Krishnas. Helen pushes back. “Some people smoke pot, some people bungee jump, some people chant,” Helen says. “What do you do to be happy?”

“Nothing,” Jessica shoots back. “I’m not.”

Jessica says it doesn’t matter if she’s happy. She has a job. She’s accomplishing something in the world. What exactly is she accomplishing? Well, she’s being a grown-up. Helen thinks seeking personal enlightenment is actually less selfish — or at least more productive — than being miserable all the time. “Are you saying that my life has no value?” Jessica asks defeated.

“No, I’m saying that maybe underneath all the neurosis, you have a profound capacity for happiness that you’re not allowing to exist.”

Jessica protests once again. She knows herself too well. She knows her limits. She knows how she’ll react to everything. Then Helen kisses her. And, well, turns out having a hot woman’s tongue in your mouth actually does approach something like profound happiness.

Helen and Jessica start to date and it works. Jessica is suddenly much happier — confusing everyone especially her boss/ex Josh Meyers. But Jessica still can’t quite live for herself. She makes Helen move comically slow and on the day they’re finally supposed to have sex she accepts her mother’s invitation to Shabbat. Even when they settle into the groove of a relationship, Jessica keeps it a secret. She doesn’t even tell her therapist. “I’m a Jew from Scarsdale,” Jessica panics. “This has to stop.”

If you talked to my parents they would tell you I’ve always done exactly what I wanted to do. They would say I’ve always been stubborn, never planned to stay in my hometown, always wanted to be an artist, and never felt anything like social or familial obligation. They would be wrong. It’s true that I’ve always been someone incapable of lying to anyone except myself, but I spent the first 23 years of my life trying to both live truthfully and appease my family, my friends, my teachers, and society the best that I could. The same way Jessica rejects men but continues to panic about finding a man, I rejected my family’s expectations while still carrying an immense amount of guilt. The panic, the guilt, it didn’t do anything except send a message to my parents that my defiant choices were making me miserable.

Then I came out.

We think of coming out as an embrace of our gender or sexuality or both. But coming out freed me in ways that go beyond this base understanding. Suddenly, doing what I was supposed to do became so far out of reach that it ceased to exist. My whole life I felt like I was failing to follow the rules but all of a sudden I found myself playing a new game. I learned how to set boundaries, I learned how to let go of my guilt, I learned how to focus on myself. These changes didn’t make me more selfish — they did the opposite. All of my relationships — familial, romantic, friendships, societal — became deeper and more authentic.

The best moment in Kissing Jessica Stein is when Judy talks to Jessica on her porch. It’s the day before Jessica’s brother’s wedding and Helen has just ended their relationship. Jessica wouldn’t come out and Helen was tired of being a secret and now Jessica is alone and wondering if she’ll always be. Jessica’s eyes glisten with tears. “You’re my love, you know that? My beloved.” Judy says. “But sometimes I worry for you.”

“I worry for me too,” Jessica cries.

Judy tells an anecdote. When Jessica was in 5th grade she was cast as the lead in the school play. She was thrilled. But after the first day of rehearsal she quit because her costar wasn’t good enough and if the show wasn’t going to be good enough she wanted no part in it. Jessica’s replacement turned out to be terrible and her costar turned out to be excellent and Judy suggests Jessica could’ve been so much happier if she’d just done the play — if she’d taken that risk. “I think,” Judy’s voice cracks and she pauses finding a smile. “I think she’s a very nice girl.”

Jessica’s head flips around. Her mom knows about Helen. Her mom approves. It was never about controlling the direction of Jessica’s life — it was just about wanting her daughter to be happy. Judy just assumed happiness meant marrying the shul’s latest eligible bachelor. But when she’s shown an alternative? When she sees her daughter finding happiness in her own way? She’s happy too. This scene is wish fulfillment for many a queer, but it works because at its core is a painful truth: heteronormativity, and even homophobia, can come from a place of love. Judy is probably the reason 5th grade Jessica quit the play — Jessica’s perfectionism comes from somewhere — but that wasn’t her intention. It’s taken Jessica’s queerness to reveal the fact that Judy just wants her to be happy whatever that ends up meaning.

Of course, Jessica’s queerness is itself debatable and this brings us to the film’s controversial end. Jessica and Helen reunite and start a real relationship and months pass and then it’s over. Helen ends it, because Jessica doesn’t seem that interested in her sexually. More months pass. Now Jessica is working full time as a painter, she’s stopped straightening her Jewish curls, and she’s developed a friendship with Helen who has a new girlfriend. She runs into Josh Meyers and this gay romcom seems to have a straight happy ending.

I used to hate this ending. I related deeply to Jessica and her rejection of queerness felt like a betrayal. But the years have passed, and as my own queerness has changed my relationship to my family and myself, I’ve realized I’m really more of a Helen anyway. The fact is queerness freed Jessica from the confines of an expected life and whether she wants to date another woman or settle down with Josh Meyers that will always be true. That’s the power of a queer identity — no matter how short-lived.

It’s true that living for others is a tenet of Judaism. But the only way to live for others is to live for yourself enough that you know which others you want to live for. Queerness gave that to me. I’m still an anxious Jew. I’m writing this on Rosh Hashanah. Ruth Bader Ginsberg just died. We’re a month and a half away from an election I have no faith in during a pandemic that seems to have no end. I feel more uncertain about my actions than I have in years. Writing this review of delightful romcom Kissing Jessica Stein feels like an absurd thing to do given the circumstances. But what I know is my queerness has given me a clarity to approach even the toughest moments in a way I couldn’t before. It guides me and my Judaism guides me and even if I still don’t have all the answers I’ve accepted that I’ll never have all the answers. That’s kind of the whole point. Happy new year everyone.

You can watch Kissing Jessica Stein for $3.99 on Amazon Prime. 

Want more movies? Check out Autostraddle’s 200 Best Lesbian Movies of All Time.