I’m on Facebook, and I see that somebody has requested to be my friend. It’s this gay guy who likes my style, who says he wants to get to know me better. I think, “Why not?”

While flipping through several of the 680,000 photos that are posted to his profile, I realize that I like his style, too. But I initially do not like his face. Everybody knows that when you meet somebody online, one of two things happens: you either become friends or you date. In my profile photo — the one that solicited his interest — I’m standing in front of this graffiti wall, and I’m wearing a shiny black vest, size XS from American Apparel (which I had to buy in New York because there is no AA in New Haven), a black hoodie also from AA, black ankle boots I just got at Thom Brown, black Cheap Monday’s, and this thin grey scarf with skulls on it.

So I allow this gay guy to be my Facebook Buddy (FB), and once I give him my AIM screen name we start chatting. The boy is from California, goes to FIT and works in a boutique. Ordinarily, a match made in heaven. But not this time, because he also tells me that he’s really into Britney Spears. Strike one. He worsens this by proudly telling me that he’s kind of crazy. Strike two. In the final blow, he clinches the downward trend our chat is now taking by basically telling me that we won’t be sexually compatible. It turns out that we’re both right-sided Prada pumps. And everybody knows you can’t walk without the left pump. Strike three.

For reasons I am not prepared to explain, when he asks me out on a date I actually say yes. I knew that he wasn’t really my type, but I went in thinking that maybe we could come out of it good friends. After all, we have such similar styles and interests in fashion, how could we not? And then I started to wonder: Do the clothes make the man?

How many of us have had that fixer-upper boy/girlfriend, that frumpy person with a heart of gold who happens to also make us frown each time they get dressed in the morning? One of my first and best boyfriends was this graduate student named Jess I dated back when I was an undergrad. Because of this cross-generational fertilization, I thought I was the hottest shit on the block. But Jess was far from fashionable — not quite frumpy, though he did love a big sweater. Jess was more the “I-eat-organic-foods-and-then-go-to-the-gym-and-afterwards-we’re-going-to-camp” type, and I was the more “Um-I-can’t-go-camping-because-Raf-Simons-doesn’t-make-camping-gear” type.

But despite what little style Jess and I had in common, our relationship trotted along just fine. I would jokingly call him a lumberjack and he would equally jokingly call me a prissy queen. But then we’d end up doing the lumberjack/prissy queen dance. In our case, the clothes didn’t make the man, because, well, most of time we weren’t wearing them.

That said, though, I gotta admit that when I see a guy to whom I’m attracted, the first thing I usually notice about him is what he’s wearing. If I see a smartly dressed guy, I’m going to look, partly because he might be hot, partly also because I’m fascinated by people who care about their appearance. That’s because what we wear says a lot about who we are.

When I see a gay boy in a shirt that says “Abercrombie,” for instance, I automatically assume that 1) he goes out in Chelsea or someplace like it; 2) he probably has the exact personality of a shopping mall; 3) that he probably doesn’t like black guys.

It’s fifteen minutes before my date with Britney Spears Guy (BSG), and I’m freaking out because I don’t know what to do on it. I already deeply suspect that he is not going to be my type, and I’m repeatedly asking myself how I got into this situation. “We’ll have a lot in common,” I think. But I’m so nervous that I call my friend Wil who gives me the following highly effective contingency plans:

Contingency Plan 1) “Girl, if you don’t like him, just fag it out! When he comes to the pizza place, just be like, ‘Haaaaaaaay girl!’ And snap your fingers a lot.”

Contingency Plan 2) “I’ll call you at 11:30 to say that ‘Something bad happened.’ Then you tell him that ‘Something bad happened,’ and you book it!”

When BSG shows up, he’s wearing a blue hoodie, light grey skinny pants and these patent leather Vans. We talk about fashion houses, labels, Raf Simons, John Galliano. And that’s really about it. After like 20 minutes, I don’t have anything else to say to him, but he wants to keep hanging out. And then he tells me that he wants me bad, and that’s when I go, “Something bad happened.”

Where our date really went wrong was in my naive belief that two fashion-conscious people could have something in common that was unrelated to fashion. I imagined that, even if we were missing the left Prada pump, we could still have a meaningful conversation. It gets really tricky, though, because people always say things like “opposites attract” when actually, “similars” attract. I couldn’t talk to BSG anymore because there was nothing left to talk about. People who have bad dates say things like, “We had nothing in common.” It might be a cliche, but in this case it’s actually true.

I guess I had this idea that all fashion-forward people are fabulous and interesting. I then realized that fashion is there to get that initial spark going — it’s like the ice-breaker. It’s the incentive to unwrap the package. Nobody wants to open an ugly gift. But you know what? Sometimes, people are just fuckin’ weird, and not even a hot Balenciaga bag can save them.

Madison Moore is filled with scorn for the homely and poorly dressed.