Just in time for the release of Jennifer Westfeldt’s newest film Friends with Kids, here’s Bri Lafond with another look at Westfeldt’s breakout indie. In it, Lafond is confronted by the divisive comments of her fellow movie-watching friends, outdated tropes left over from the 1990s, and an unfortunate dearth of Jon Hamm.

The first time I watched Kissing Jessica Stein, I loved it. I fell for cute-as-a-button Jennifer Westfeldt, and I thought the movie was a clever twist on the standard romantic comedy. I dug it so much after having it recommended and lent to me by a friend, I went out and bought my own copy, watching it several more times over the next few years. I identified with Westfeldt’s chronically neurotic Jessica; I yearned to be as cool as Helen — played by Westfeldt’s co-writer, Heather Juergensen. This was the kind of movie I sat through the directors’ commentary on, I was so into it.

My revisitation of Kissing Jessica Stein was emphatically more fraught and downright divisive than I thought it was going to be. I sat down to re-watch the movie with two friends of mine: James and Missa. From the first few minutes of the movie, it was clear that they weren’t as charmed by the world of Jessica Stein as I first was almost ten years ago. There was a lot of eye-rolling and playing with cell phones throughout the movie’s first half and an authentic frustrated walkout during the second. Could I have been so wrong about Kissing Jessica Stein?

In a word: no. However, I do understand my friends’ frustrations with the movie. We sat down after the movie was over to discuss it, and they each brought up some salient criticisms. James’ primary gripe with the movie was the material’s theatrical air. Kissing Jessica Stein started out as part of a stage play written by Westfeldt and Juergensen called Lipschtick, and its theatrical roots definitely come through in the movie version. The dialogue has just a little too much polish, the characters are just a little too clever, some of the cast’s mannerisms are just a little too rehearsed. This aspect of the movie doesn’t bother this old drama club kid any, but I can understand how others would be bothered by it. The theatrical refinement led to another problem for James; as he put it, the movie is “too smart to exhibit any real emotion.” For him, any time the characters get close to an authentic emotion, they pull back in favor of getting the laugh line. For example, during what is arguably the film’s emotional climax — when Jessica and her mother (played by the fabulously theatrical Law & Order mainstay, Tovah Feldshuh) have a tearful discussion talking around Jessica’s desire for Helen, the two don’t confront the issue of Helen directly; they launch into an elaborate story about a play Jessica was in as a child that she didn’t want to perform in unless it was going to be perfect. Hello, metaphor! I have to admit — and I don’t know how much this was colored by my re-viewing company — some of these moments that I thought were clever ten years ago did end up coming across a little too pat. So many times on this watch, I thought of Internet movie reviewer Film Brain’s catchphrase: “SYMBOLISM!!!” (http://www.youtube.com/watch?v=JMNuDKd5XfM).

Missa’s problem was a little more ideological, but it did run up against some of what James was complaining about. Missa found herself offended by the movie’s “temporary lesbianism” conceit. What I saw as a willingness to reject a set gender identity in order to experiment, she saw as a typical 90s pop culture trope: “There was this idea in so many 90s movies and television shows that someone could suddenly ‘turn lesbian,’ rejecting everything that had come before. Joss Whedon did it with Willow. Kevin Smith did it with Chasing Amy. Frankly, it’s insulting.” I have to agree with Missa to some extent here; this idea definitely popped up quite a bit in the late 90s when Kissing Jessica Stein was first coming together as a stage play. For some reason, it never particularly offended me that Jessica “turns lesbian” because, in fact, she doesn’t: Jessica merely experiments with the idea, lets her guard down, opens herself up to a relationship with Helen, and doesn’t try to identify with lesbianism as an identity. Helen’s character arc is a bit more problematic. Over the course of the movie, it’s implied that Helen actually has “turned lesbian,” rejecting her identity as a straight woman with several male partners that she is apparently emotionally and sexually unfulfilled by, she ends up in a committed relationship with another woman by the film’s end. There’s even a “becoming lesbian” montage for Helen in which emotional music plays over scenes of her weeping with and subsequently being hugged by her gay guy friends. Despite all this, I was still willing to give the movie the benefit of the doubt: though Helen ends up with another woman and it’s implied that Jessica might end up with former lover Josh, I still viewed the women’s sexualities as more fluid than binary categories.

Going back to the idea of “turning lesbian” as a 90s trope, James picked up on this thread and connected it back to the movie’s writing: “The movie covers a lot of the same territory as Chasing Amy, but Kevin Smith still managed to evoke some genuine emotion. Instead of hitting the laugh line right in the middle of things, he’d hold a beat and give it at the end of the scene. Or he’d hold off on the joke entirely for a scene or two to develop Holden and Alyssa’s relationship.” I do agree with this assessment. There is something kind of surface-level about Jessica and Helen’s relationship. The most emotional scene between the two occurs near the end of the movie when Helen decides to leave Jessica, telling her that they “are more roommates than lovers.” After Helen explains to Jessica that she feels they are best friends as opposed to romantic partners, Jessica responds: “Yeah. Isn’t it great?” It’s one of those moments that is clearly intended to elicit a laugh from the audience of a play and ends up undercutting the seriousness of the moment.

Though I’m not as enchanted by the movie as I was when I first watched it ten years ago, I’m not as emphatically against it as my friends are. I think it’s a cute, quirky romantic comedy that has some theatrical sensibilities. It’s not a perfect flick, but it’s a fun time if you’re game for it.

Here are some of my notes and additional observations:

  • I forgot how beautifully damn Jewish this movie is. The film opens in temple on Yom Kippur with Tova Feldshuh playing the role of Jessica’s yenta mother to the hilt.
  • The soundtrack for this movie is a fun, eclectic mix: Ella Fitzgerald, Blossom Dearie, Dave’s True Story. Definitely worth a listen even outside the context of the movie. Especially Dave’s True Story. Look up “Sequined Mermaid Dress” and “Crazy Eyes” on the YouTubes, man.
  • That Rilke quote has always struck me as a bit much. And I like Rilke. I can only imagine what Helen had to pay to put that entire Rilke quote in the classified section. To wit, the quote in full:

It is not inertia alone that is responsible for human relationships repeating themselves from case to case, indescribably monotonous and unrenewed: it is shyness before any sort of new, unforeseeable experience with which one does not think oneself able to cope. But only someone who is ready for everything, who excludes nothing, not even the most enigmatical will live the relation to another as something alive.

  • Also in regard to that Rilke quote, how is that kind of thing supposed to pull in mad pussy? These fantastically stereotypical gay guys are way off-base.
  • The whole newspaper angle in this movie is preciously quaint. Classified ads. People getting paid to write articles. Actual newsprint. Too cute.
  • There’s a blink-and-you’ll-miss-it cameo from Westfeldt’s longtime boyfriend Jon Hamm in the dinner with friends scene. It made me sad to see him come and go so quickly. Come back, Jon Hamm! Sex things up!
  • Apparently, Josh is played by some dude who was on Gilmore Girls? According to Missa? Apparently? All I know is, I agree with James’ assessment of him: “If they were trying so hard to get a Jon Hamm clone, why didn’t they just use Jon Hamm?” As I recall from the director’s commentary, Hamm had a conflict during filming, but I think he was supposed to initially play Josh. Our loss.
  • Josh’s kiss-off to Jessica during the dinner with friends scene is so damn mean and polished, it’s clear he’s been practicing that speech. I remember thinking it was way too mean to be real ten years ago, too.
  • I still love the “sexy-ugly” discussion. I totally get it and I’m a believer. I don’t care if it’s too polished or too worked: it’s bloody brilliant.
  • The lipstick blending conversation caused a damn uproar as we were watching this. To wit, Helen talks about blending lipsticks to achieve the perfect look while Jessica says she keeps looking for the one perfect lipstick. This got a “SYMBOLISM!!!” shout from Missa, a “talk about lipstick lesbians” comment from James, and James’ brother came in from the next room to see what all the commotion was about.
  • During the scene in which Jessica and Helen sneak into the newspaper office for something or another and run into Josh, James had this to say: “That’s a Human Resources phone call just waiting to happen.”
  • Helen sneezing on her boyfriend (Which boyfriend? The sexy delivery boy wearing a cowboy hat.) was “the final straw” for James. As you may or may not recall, it’s Helen sneezing and getting sick (even though she “never gets sick”) and has to rely on Jessica to take care of her that pushes their relationship forward. It is a bit cheesy that we get the “I never get sick” convo and then Helen sneezing out of fuck-nowhere.
  • The scene where Josh finally confesses his feelings to Jessica on the roof and asks her out to dinner and Jessica says she can’t because she’s “with Helen” and Josh says “You’re having dinner with Helen?” That scene? Yeah, that’s the one that caused James to walk out. After much cajoling, he returned, but under protest: “I’m offended that the writer is the dumbest one in the room!”
  • Though they may not have believed in Jessica and Helen’s relationship, the scene “three months later” when they break up royally pissed off James and Missa. I’ve heard this complaint from fans of the movie, too. Why can’t Jessica and Helen just end up together? Why do we have to undo everything in the end? I do think keeping them together would cut off a lot of criticism, but… I don’t know. I’ve seen the movie so many times, I can’t imagine it any other way.
  • One last “SYMBOLISM!!!” scene comes during that last bit at the bookstore. Jessica is there to put up fliers for her art show, Josh is randomly there holding a coffee, the two reconnect, and there’s a hint they might end up together (though I maintain that there’s a bit of a flirtation with that female bookstore employee). Josh is wearing a shirt with some holes in the back of it because he’s a struggling writer now, right? Because they’re both being authentic artist-types now. James: “The subtlety was so subtle I almost missed it.”
  • A collection of some of my favorite phrases and comments uttered by our group during the film:
    • “Rebound: The Movie”
    • “That damn kitten has turned in the most authentic performance so far.”
    • Regarding the pregnant friend: “Always with this ‘glowing.’ Green Lantern glows and he’s not fucking pregnant.”
    • “Bring back Jon Hamm. I need more Hamm.”
    • “You can see the damn seams on this thing.”
    • Regarding Helen’s “amazing” pants: “My god, those pants are horrible.”
    • “HD has not been kind to this movie’s low budget.”
    • “You can’t argue with a Jewish mother.”
    • Regarding Josh and Helen speaking in unison: “DID YOU GET IT?”
    • “Track marks from diabetes? Now that’s funny.”
    • “Of course we don’t get to see her fucking painting. The fucking painting we always keep hearing about that’s so central to her fucking character.”
    • “At least Kevin Smith dialogue would have curse words to occupy us.”
    • “There’s a whole other act to this fucking thing?!”