It’s Romance Week at MovieJawn! All week long we’re getting all mushy about love in the movies!

by Matthew Crump, Staff Writer

There’s almost no genre of film that I would consider myself a scholar of, but rom-coms released around the turn of the century are perhaps the one exception. Since childhood, I have had a borderline religious worship of  deep respect for professors like Sandra Bullock, Meg Ryan, and, above all others, Dr. Julia Roberts. The only issue is, most of what I learned from my education at the school of Romance Sciences (with a concentration in Meet-cutes) was almost exclusively straight.

Turns out, while I was subconsciously clinging to supporting characters like the beauty pageant coach in Miss Congeniality or the GBF in My Best Friend’s Wedding, the independent cinema market was already producing rom-coms with LGBTQIA leads. While the late 90s/early 2000s was an exciting time for the sad, gay, hopeless romantic, it’s also true that the roots of this queer cinema subgenre saw some less-than-favorable representations of the community before it started producing mainstream rom-coms like Love, Simon and The Half of It.

But I’m not here to discuss queer representation in cinema. I’m here to use my expertise as a rom-com connoisseur to offer a completely objective ranking of 10 queer rom-coms so you and your partner can choose a less heteronormative option for a Valentine’s Day movie night. 

10. The Watermelon Woman (dir. Cheryl Dunye, 1997)

I know how these listicles work. You’re going to look at the lowest ranked entry so you can turn your nose up at it, maybe skim through the next few entries, then scroll down at the speed of light so you can see if you agree with what I gave the #1 slot. Well GOTCHA. As the first film ever directed by an openly queer black woman, The Watermelon Woman is not only the biggest trailblazer, but it’s probably my favorite movie on this list. 

So why did I give it the lowest ranking? Because, as we all know, cheesy rom-coms aren’t supposed to be progressive. They’re supposed to make you want to give up a lifetime of radical feminism so you can go live in a cottage and iron your husband’s pleated khakis all because he happened to push you out of the way of that semi-truck when your high heel got stuck in that city sewer grate while holding 14 cappuccinos that you had just picked up as part of your new internship. Or something like that.

Anyway this movie is incredible. It just has a 3-dimensional protagonist with actual goals that aren’t completely centered around a love-at-first sight kind of romance. That is simply not the goal of this listicle. At least now I have maximized the chances of this underground Philly-filmed indie being on your radar before you skim/scroll through the rest of this. If you want to read a more in-depth gush I wrote about this film, go buy this zine.

9. Chasing Amy (dir. Kevin Smith, 1997)

Okay, at the risk of ruining the budding friendship I have with fellow MJ Staff Writer Emily Maeser, Chasing Amy is the actual lowest ranking film on this list. Not because it isn’t a quality film, because, again, this listicle isn’t about film quality. My goal here is to find you the most satisfying cheesy queer rom-com for Valentine’s Day, and I’m not even sure this movie counts as a rom-com. I’m also not sure director Kevin Smith has ever met a real-life lesbian. However, I decided to keep it on the list because as far as Smith’s “Askewniverse” is concerned, this is certainly the closest you’re going to get. And even though Google just told me the term “bisexual” has been around since 1892, we’re gonna let this one slide since it’s the oldest film on the list. Again, if you want to read a more in-depth gush that Emily wrote about this film, go buy this zine.

8. Edge of Seventeen (dir. David Moreton, 1998)

This movie is also probably not a rom-com. Please don’t get frustrated, you aren’t the one who has spent hours upon hours digging through low-budget, mildly offensive gay movies to build this haphazard ranking. The reason I’m keeping Edge of Seventeen in the running is because it managed to capture the essence of a 1980s John Hughes film by following a teen in pursuit of love (i.e. rom), laughter (i.e. com), and also the complexity of coming out (i.e. vom). I also just can’t help but appreciate the film’s commitment to the authenticity of what it’s like to come out by not forcing a resolution to a difficult moment with a cheap laugh. Also, it stars queer icon Lea Delaria.  

7. Adam & Steve (dir. Craig Chester, 2005)

This movie is the first official rom-com on this list. Just to be totally clear, this means it is the worst of the rom-coms and only climbed to the 7th slot on a technicality. 

Adam & Steve made me ashamed to be gay. If you are straight, you aren’t allowed to watch this movie. Sorry, I simply won’t risk a straight person watching this movie and thinking this is anything close to what it’s like to be queer and pursue romance. Seriously, if you’re straight, just go to the next entry.

If you’re still here for this paragraph, that means you’re gay and want to know more about this shitty movie. I am choosing that adjective very intentionally, as the opening sex scene in this movie literally ends with one of the men doing too many poppers and shitting himself. I hated it. I hate that this is what we have become. The rest of the movie was a lot of stereotypes and Parker Posey making fat jokes then somehow falling in love with Chris Kattan? There was also a back-flipping knock-off Brokeback Mountain man and Jackie Beat playing a Party City version of Trixie Mattel. See? Only gay people will understand that sentence anyway. Basically, if you’re into self-immolation or any of the movies from the Eating Out franchise, this is the rom-com for you.

6. Better Than Chocolate (dir. Anne Wheeler, 1999)

This rom-com had me crying with laughter, but only during scenes where it was trying to be sexy. Otherwise, it does not excel in either the rom or com categories. However, it is a very watchable, (mostly) light-hearted movie about two lesbians who make absolutely no sense together. There’s also some (mostly) good representation of a trans woman who also gets to fall in love! So that was cool. Basically, I can’t tell if I liked this movie or if I just liked how much Ani DiFranco was on the soundtrack. Do with that what you will.

5. The Object of My Affection (dir. Nicholas Hytner, 1998)

Was I the only one who had never heard of this movie? As someone who is proudly riding the new wave of people finally admitting that they are unreasonably attracted to Paul Rudd, I was thrilled to find out he not only co-starred in a film alongside rom-com underdog Jennifer Aniston, but that his character was gay. If I had seen this movie during my more impressionable years, there’s no doubt in my mind I would have followed in his character’s footsteps and be teaching first grade while platonically raising the product of my straight bff’s unplanned pregnancy right now. The plot of this was pretty wild but, before it totally spun out of control in the third act, I was really enjoying the ride. It’s also the first script on this list not to use a slur! Who knew that LGBTQIA oppression ended in 1998?

4. Imagine Me & You (dir. Ol Parker, 2006)

I might get in trouble with my roommates who I pressured into watching this movie for not ranking it higher on the list. While I don’t think this movie is good enough earn a medal in the Queer Rom-Com Olympics, it certainly is a strong contender. It has all the classic trademarks of a rom-com, complete with a love at first sight sequence between two women that literally happens while one of them is walking down the aisle to marry a man. Big drama.

This movie is often heralded for being the first to break away from the tendency lesbian dramas have to break up/kill off their main characters. While its plot offers a much needed happy ending, I still couldn’t help but feel bad for the straight man who a mere hour and half earlier thought he was signing up to spend the rest of his life with his childhood sweetheart. And I almost never feel bad for straight men. Maybe it’s just because of the British accents, but the plot of this movie just felt like a much longer, more cutesy version of the gay subplot in The Haunting of Bly Manor. Also, Lena Headey’s lower back tattoo is atrocious.

3. Kissing Jessica Stein (dir. Charles Herman-Wur, 2001)

This is a very controversial, yet brave ranking on this list because Kissing Jessica Stein is widely hated by most WLW folx. However, as we established, no one working in the film industry during the late 90s/early 2000s knew about bisexuals. If it weren’t for the last 10 minutes of this movie, it might be the perfect queer rom-com. Regardless, (spoiler alert: here comes the controversial, yet brave part) I kind of like the fact that the ladies don’t end up together. 

Hear me out, this movie manages to take the stereotypical “neurotic small town girl working at a newspaper in the big city” rom-com archetype, and give her the opportunity to explore her sexuality in a really genuine way. It’s also funny as hell. By far, this is the film on the list that made me laugh the most. The fact that Jessica and Helen break up and Jessica winds up going back to a man admittedly feels regressive, but only if you regard Jessica strictly as a lesbian. If you just assume that the main characters are both bisexual, as almost all of their character building points to, this ending is really heart-warming. The fact that the two women stay close friends is a very real dynamic that a lot of queer people share with their exes and something I had never seen represented on the big screen. 

I don’t know y’all, maybe we really would be better off without those last ten minutes. If you choose this one and it leaves you feeling like you need a drink, you can get the recipe for Kissing Jessica Stein-themed cosmo from this zine (seriously, go buy it).

2. Saving Face (dir. Alice Wu, 2004)

Thank gay god for this movie because as far as I can tell it had to carry all non-white queer people on its back for almost an entire decade. With the exception of underground films like The Watermelon Woman and Punks, a Black rom-com that’s all but disappeared, Saving Face is the first queer rom-com to follow a protagonist that isn’t white. And a love interest that isn’t white. Pretty much no one in this film is white except a woman that works with the protag (who coincidentally is most famous for playing Ross’ lesbian ex-wife on Friends).

Besides the obvious milestones this film passed in telling a story about two Chinese-American lesbians falling in love, just looking at the film strictly for it’s rom-com quality, it’s done more than enough to earn its spot at the top of this list. Saving Face checks off every rom-com moment you could imagine, from leaving behind flirty notes in inconspicuous places all the way to a chase through the airport to make a declaration of love. Even with its loyal subscription to the rom-com genre, the film still manages to challenge cliches and maintain a plot that feels fresh. The protagonist sees a satisfying character arc while bouncing between dual plotlines; one about her new girlfriend and the other about her aging mother’s secret pregnancy. Again, big drama. 

1. But I’m a Cheerleader (dir. Jamie Babbit, 2000)

OKAY FINE. Of course this is the number one slot. This is every queer person’s fav rom-com, I know I’m not being original here. Why don’t you watch something different this year though? Just consider it. There are nine other options on this list, you could pick any of them. I know you probably didn’t read any of them and just scrolled ahead to confirm your bias for But I’m A Cheerleader, but I’m telling you, there were more queer people in cinema during this era besides Clea Duvall. 

Just take two more minutes of your time, scroll back through this listicle, and promise me you won’t let the number of times you rewatch this movie surpass the number of years you’ve been alive. Oh, and have a happy Valentine’s Day!