Millennial Queer Girl Reviews ‘Kissing Jessica Stein’ & Why Didn’t Anyone Warn Me?!

Uh, is this considered a “lesbian” movie?

I have a confession to make: before starting this column, I had only seen about 2 classic lesbian films. I know, I’m a bad queer. When I admitted this to my fellow GO coworkers, they were appalled. Two of them quickly listed off at least 10 films I needed to watch right away. I rapidly wrote down the titles (for research, obviously).

I want to take you all along with me in my quest to review all of the lesbian classics through my Millennial queer lens. Last week, I reviewed the emotional and hella long “Claire Of The Moon.”

This week, I watched “Kissing Jessica Stein” and I’m not even sure if it’s a lesbian film. 


I hate to say this y’all, but at this point in my experiment of watching all the lesbian classics, I’m getting a little annoyed. I’m not annoyed at the steamy make outs or the queer representation on the big screen. But I’m SO annoyed by the majority of lesbian films centering around cis, straight men.

But I’m hanging onto hope this week with “Kissing Jessica Stein.” At the first scene, we meet a charismatic and ambitious 28-year-old Jessica Stein, a journalist living in New York City. She’s helplessly single and everyone seems super stressed about it like she’s running out of time.

As Jessica goes on a plethora of boring AF dates with men, we meet a new character: a brazenly sexual woman who is running a sexy art gallery, Helen Cooper. She’s hanging out with her gay men BFFs when she admits she wants to explore her sexuality through placing a newspaper ad. While Helen has previously explored loving women, she admits to not taking it seriously before and has never been out. She puts in the ad because she’s ready to take her desires more seriously now. (Side note: who knew that people put cruising ads in the newspaper back in the day?! Juicy.)

Of course, Jessica sees the ad when she picks up a copy of the newspaper because Helen quotes her favorite author and it seems like fate. After the worst dinner set up ever, where her boss (who she used to date) is a total misogynistic pig, Jessica decides to call Helen to meet up.

As Jessica walks into the bar, she blurts out to Helen that “this isn’t really me” — “this” obviously meaning lesbian things. In her most charming of ways, Helen convinces Jessica to give it a shot anyway and they get to talking over wine. As the women share a cab to their dinner date, Jessica asks Helen what kind of lipstick she’s wearing and the women share the sexiest exchange of talking about different shades of lipstick. I love femmes dating other femmes.

As Jessica opens up about her fears around dating women, Helen responds that she dates both men and women. “I just find a lot of different things sexy,” Helen says.

At this point, I’m getting kind of annoyed at Jessica. She’s like so basic and stuck in her ways as she judges the tambourine playing Buddhist’s at Union Square for “not taking life seriously enough.” I am totally falling for Helen, though. She’s bold and courageous and expansive. As the two women come to odds at the end of their date, Helen goes in for a kiss to prove to Jessica that she needs to go out of her comfort zone sometimes.

Jessica decides to give it another shot.

“Whatever I’ve thought about lesbianism in the past, I’ve always thought ‘ew’ but I had such a wonderful time with you the other night,” Jessica says before she delves into copious amounts of research on lesbian sex.

The movie cuts to a montage of the women making out but not going any further. Helen seems very frustrated with Jessica’s desire to take it super slow because she is craving something more and Jessica is being incredibly clinical about her desires. They keep spending time together and it starts to get more intimate when Helen is sick and Jessica steps in to take care of her.

Just as the women are about to have a date to finally have sex, they get roped into a family dinner at Jessica’s house where there is an obvious setup with a boring AF man. And her awful boss/ ex-boyfriend finds himself there, too. The blessed gendered bedrooms during sleepovers because Jessica and Helen end up in bed together.

After the first night they f*ck, the film fast forwards three months. While the couple seems fabulously in love, they’re both struggling with being closeted in their relationship. While Helen is fighting with her gay BFFs about not being out — Jessica comes out to her coworker and friend Joan.

Photo by Kissing Jessica Stein

Jessica finds herself drowning in a sea of lies about her relationship. “It makes me feel like you’re ashamed of me!” Helen screams on the street when she finds out that Jessica didn’t tell her about her brother’s wedding. They break up when Jessica refuses to take Helen to the wedding as her date.

The sweetest moment happens when Jessica is sitting with her mom after the rehearsal dinner and her mom turns to her and says “Jessie, I think she’s a very nice girl.” My heart just filled because she didn’t even have to say anything — her mom just knew and accepted her. After this moment, she goes home to get Helen and bring her to the wedding. From there, her coming out just explodes and her entire family knows.

It starts to get creepy as her boss/ex Josh begins to get suspicious and investigate into her life. I’m not sure if it’s because he’s going to be homophobic AF or wants to be supportive. But at this point, I’m not hopeful. He shows up to the wedding and pulls her outside to “check out the view.”

Ugh, bad feeling alert. It’s not that he’s homophobic AF or that he wants to support her — it’s that he wants to use her as his creative crutch, his muse for his writing. God, when are men going to stop turning women into props? I really didn’t want another lesbian film focused around a dude. But alas, here we are.

The movie progresses and the couple gets extra cute and moves in together. But then things start to fall apart because they’re not having sex. Jessica feels like they have the best relationship ever with amazing communication, but Helen wants someone who craves her. And I mean, who doesn’t?! TBH, I don’t see what Helen sees in Jessica… She’s pretty boring. Of course, they break up and become *best friends* because Jessica discovers she’s really not all that gay after all! Barf.

Then, months after their relationship has ended, Jessica runs into Josh at a bookstore. And they’re flirty. Ew, gross. There is this implication that they’re going to go on a date and blah, blah, blah. Then the film fades to black.

F*CK. THAT!

My frustration about this film doesn’t come from the fact that Jessica might be bisexual or not LGBTQ at all by the end of the film — it’s that this is one of the largest budget lesbian films of its time (the early 2000s) and it got a ton of press back then. But it’s such a dangerous narrative to put out there for young queer girls who watch this movie and then believe it when people tell them they’re “probably just going through a phase.”

It’s not only unfortunate that the majority of mainstream representation queer, bisexual and lesbian women get is centered around their relationships with cis, straight men — it’s actually harmful to young LGBTQ people who look to media for how to inform their lives. I’m bored of this narrative. We deserve so much better. We deserve to have nuanced queer relationships with empowering role models.

Why didn’t anyone warn me about this movie?!

Okay, bye. Next week I’m definitely researching beforehand, spoilers be damned! I’m not watching another film centering around boring AF cis, straight men.