Recently, I received a piece of advice: "You should wear a cap." As this was unsolicited, I asked what my friend's boyfriend was talking about.

"You should get a fitted cap and wear it out if you want to pick up guys," he elaborated. "They will flock to you. Guys love guys in fitted caps."

Oh.

"I don't need a cap," I told him. I'm not a big fan of having my head covered, and I'm sure my clumsiness would have me dragging the brim on walls and hitting people in the eyes with it. A cap is one more thing to forget and I already live in fear of losing any of my 13 precious sunglasses. I don't have time for that much anxiety in my life. Wearing a cap just wouldn't be me.

But most of all, I do OK. If I see someone I like the looks of, I say something. Beyond that, I don't need anything, certainly not a flock. I don't even know if I could value one that came as the result of a cap, which I've long considered the cheat of cheats — the easiest, most temporary way of projecting butchness in the entire Land of Gay.

The cap will get you every time. Look past the cap. Never trust a big butt and a cap. These are the things I believe because I know the power of the cap. I even mentioned it last time. The cap works.

Plus, my head is buzzed, my shoulders are broad and my arms have muscles on them. Like I said, I do OK and I do it with the wind in my follicle sprouts.

As a gay man, I find myself consumed by the concept of masculinity. Yet, I have only a vague idea of what defines it: strength, evenness, self-assuredness, vigor, substantial eyebrows, beer, sports, funk. I have an even more vague idea of whether or not I possess enough of it and what to do with it. To own one's maleness is a matter of pride, but when that ownership consciously turns outward, it becomes about other people and takes on a theatrical affect. Performance is at odds with masculinity's ease. I realize that cocky bravado runs rampant in straight guys, but even there it is inherently fraudulent.

This issue becomes even more confusing for gay men. As a gay, you understand that while you'll always find peers who allow you to be exactly as queeny as you are, there is still a social hierarchy that puts a premium on masculinity. Tops are valued. "Straight-acting" is a badge of pride, despite the term's corrosiveness. I'm not immune to this – my eye wanders toward men who appear to be more on the masculine side, and I don't know why that is. Shavings of internalized homophobia that litter my brain could be the culprit. To counter, I've been considering adopting an affirmative-action policy toward femme guys. I tell myself, "Get into it," like the drag queens/all of us say.

I'm learning to not be flattered when someone tells me I could pass for straight, and that's the most confusing thing of all: for as many people who say they think I could, there are plenty of others who think that I'm flaming. I don't even know what I'm like, but I know making sure all of my sentences don't rise as they end is a full-time job - and it is exhausting.

I know the cap trick, but it doesn't mean that everyone is using it to manipulate. For some guys, a cap is just a cap. Some guys just like caps and they just happen to be gay. To what extent they use it to their scoring advantage is anyone's guess, but I'm willing to envision a scenario based in innocence. You could make a similar argument re: cheating about my buzzed head (though, it's obviously less temporary than a cap), which has its origins in my own taste for men with buzzed heads. I realized how into it I was when I realized I was into dudes and I emulated. Like I said, I tend to go for masculine dudes. There are no coincidences here.

Perhaps these signifiers that we still enlist to assert our masculinity are part of a weakened strain that was visible in the homosexuals of the ‘70s when masculinity came up from behind and really grabbed gayness by the balls. Then, it wasn't fitted caps but as Alice Echols describes in her indispensable political history of disco, Hot Stuff, "501 button-fly Levis, flannel shirts, aviator jackets, work boots and belt-dangling key chains." The "clones" of the "gay macho" movement were often mocked by the older, drag-valuing generation that felt discarded. Echols, whose history of gay macho is as succinct as you'll find, notes the underlying politics and perceived absurdity:

"As anthropologist Ester Newton discovered, gay [men in the Cherry Grove section of Fire Island – the older ones] simply took it for granted that a homosexual man ‘is effeminate, whether he likes to or not, because of his ‘female' position relative to ‘normal men.'"

Even more on point, and brought up later by Echols, is the theory that Andrew Holleran references a few times during his 1978 novel Dancer from the Dance. It suggests that the social ideal for a gay man on the scene is to be admired, and that being the recipient of the male gaze is necessarily a feminine position. "My grandmother on her eighty-ninth birthday only wished she could walk down the street and be looked at!" says the book's older, draggier Sutherland character. And then later, another character named Paul writes in a letter, "What is so incredible about homosexuals is that, if they live as homosexuals (that is to say, as women: beings whose life consists chiefly of Being Attractive to others), they die much sooner than heterosexual men."

That's a bleak view of gays and women (whose own potential sexual aggression is being underrated), but mostly it attempts to destroy a myth that a gay man can do anything to be more straight. Gayness has its own essence, its own cocktail of influences and manifestations.

The greatest irony of all happens when a man's manhood takes over, he goes bald and then he uses this object of masculinity to cover it up. I hooked up with this guy who answered his door in a baseball cap and nothing else and then wore it the entire time we fooled around. (This was something of a turn-on, really. I will admit that I am a big fan of the porn-approved turning of the hat brim from the front to the back to suck cock because I dig ceremony.) Anyway, that was weird, but not weirder than when we took a shower after and he kept the cap on. Under the water and everything. He got his hat wet as though it were his head, except it wasn't because it was a fucking cloth hat. I was praying he'd go for the shampoo bottle, but alas. This all mostly worked for him, though. He was a hairdresser and I guess he knew exactly what he needed to keep his head looking good at all times.

The crucial truth is that because gay men are still expected by society to be more feminine, we can either surprise people and get that aforementioned superficial, kind of unsavory thrill or we can just do what the fuck ever. We've all got masculine and feminine aspects to our personalities (even straight people!) and to express those things in their entirety can be great fun and liberating. I know a really beautiful kid who's thin and post-twinky, I guess you'd say, who's rarely without a fitted cap. He's stylish and isn't fooling anyone, as far as I can tell. If anything, he's giving his softer features and evident fashion investment a complement.

Last week, I started talking to a guy at a bar that I noticed from afar because of his dudeish backwards cap. I got to appreciate his wide smile and beautiful, thick eyebrows up close. And then as soon as he addressed me, he revealed himself to be less than butch. He was Spanish and enthused virtually everything that came out of his mouth in an airy way that sounded like joking but obviously wasn't – from his love of Jodorowsky and Almodóvar to his compliments directed at my body to his belief in real-life magical realism ("I think the world is magical!" he said, his entire existence twinkling).

He was really cute, and he said vulnerable things about not having a boyfriend, never having a boyfriend and his inability to figure out why. Nothing on his person predicted how soulful he'd turn out to be.

He didn't need a hat, either.

Pride & Shame is a new semi-regular series exploring sex and sexuality from the perspective of a newly single, 33-year-old, gay-sex enthusiast.

 Photo via fotoluminate/Shutterstock.