It’s about two years ago, and my best friend Aymar and I are studying in this café adjacent to the University of Michigan campus — a campus that features an American Apparel, unlike our own — where we are currently undergrads. We’re both wearing black sunglasses inside as we chisel away at our term papers. I don’t remember what I wore that day, but I can tell you that earlier today I looked really hot in this tiny leather jacket by Junya Wantanabe for Comme des Garçons and that I’m trying to figure out how many corners I’d have to stand on to be able to buy it.

We’re minding our own business, probably talking about mans, “Sex and the City,” or whether I should go to Yale, Columbia or Berkeley. In the middle of our conversation, we pause to gawk at a tall drink of water I will call “coq tees” that passes our table. CT is maybe 5’11”, somewhat pale with dark brown hair, and has these crisp blue eyes. Mmm. When he’s done passing, we both un-pause and clamor over his hotness. “It’s like buttah!” I say. Something like ten minutes later, our quick-witted convo gets interrupted by CT. We freeze. CT speaks, and this is what he says:

“Hey you guys — I’m writing a paper for a women’s studies course. YOU TWO LOOK LIKE GENDER THEORISTS, so I thought maybe you could help.”

Gender theorists.

This was, like, the funniest thing a random person had ever said to me — until it got one-upped by that guy who freaked me out in Chicago by saying, “I’m not gay, but I’d fuck you.”

Confused, Aymar and I both glance at one another, then we’re like … “Awkward…”

Long story short, Aymar, CT and I move upstairs in the café and begin an interesting conversation about a lot of stuff. Who knew that we’d end up talking to the guy we both wet our pants over?!

So this is the comical situation that led to my current friendship with CT. The only problem is … CT is an “Ambiguously Gay Straight Guy” (AGSG) — one of those “Calvin Klein Underwear Ad Hot” (CKUAH) straight guys who just love fucking with (but not fucking) the gay boys. The central feature of the AGSG is that, while seeming to flirt with the gay, they inevitably add, as inconveniently as possible:

“Well, my girlfriend and I …” and that’s when the gay boy tunes out.

But when I first met CT, he publicized the fact that he didn’t know whether he was gay or straight, and I took that as an invitation to dive right in.

The more I hang out with CT, the more I wonder: why am I bold enough to flirt endlessly with an AGSG but too timid to approach the real gays I actually have a chance to date?

I know that I come off as a ballsy kind of guy. I mean, it really takes guts to wear tiny black pants. Ann Demeulemeester knows I do love a good risk. But actually, I’m really shy and would never, ever, approach a guy on my own, let alone tell him that I like him or ask him out. The first thing that happens when I’m at a club and a boy notices me is that I unintentionally ignore him. Like last Saturday, when my partner-in-crime and I were out in Brooklyn and this group of smoking hot Israeli guys tried flirting with me. One of the guys goes, “Hi! How are you?!” What did I do? I looked at him like he was a fuckin’ idiot.

However, when it comes to CT and flirting without a dollop of shame, I really lay it on thick. I’ll say things like, “Close your eyes and enjoy yourself.”

It’s last week, and CT and I are talking about sex. Throughout the following conversation, imagine “shopping” as a euphemism for “oral sex.” So anyway, CT tells me that he likes “shopping” in the “Women’s Department” and that he’s found “an outfit” that makes women go nuts. I try to hold down my lunch. He laments the fact that a lot of the girls he’s been with hate “shopping” in the “Men’s Department” and have no idea what makes a good “men’s outfit.” On behalf of gay men everywhere, I naturally offer a free consultation.

I know that I’m tempted to flirt with CT because it’s easy, or because I wish that he would like me back. But it’ll prolly never happen. In all fairness, though, CT started it. CT is the one who said that he didn’t know if he was gay or straight. CT is the one who went to Europe and came back with tales of making out with guys. CT is the one who flips through a book of naked mans and says things like, “That’s hot.” And CT is the one who kisses you on the cheek to say goodbye, and not in that fancy European way, either.

I might be wrong, but I think that every gay boy has an AGSG in his circle. It’s nature’s way of dangling the last pair of size 6 black Dior Cuban heels in your face, on sale for 97% off. If only you weren’t a fucking size 9! Sometimes the AGSG teases you, sometimes the AGSG is actually confused, and sometimes you really get to bag him. But most of the time, I bet the AGSG is just a really hot guy who is comfortable with his sexuality and narcissistic enough to want attention from as many directions as possible. I remember once last year when CT and I went out, and within seconds of entering the place, the gay boys practically threw their “2xist” underwear at him, and women were trying desperately to get into his CrackBerry. But hahaha, bitches!!! I was the only one going home with CT that night!

I love CT, but I should probably get over my shyness and redirect all that boldness towards actual gay mans. Hey Chris, want to go on a date?

Madison Moore is always willing to “shop” if the “price” is “right.”