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1 June 2010, 4:37 pm 14 Comments

Zack's Ramblings: Horny Eye for the Preppy Straight Guy

This post was submitted by Zack Rosen

Just the other day I gave myself whiplash because a blond boy walked by with Nantucket red pants, a popped-collar polo and boat shoes. His backwards white baseball cap glinted in the May sunlight and time stopped. It doesn’t matter what these boys look like. No matter how ruddy their faces or dead their eyes, no matter how much they look like they’re gonna hit me when I check them out, they will always be a weakness.

This is because, in my experience, this breed of guy never comes homo. They just don’t. That is why untold legions of fags try to dress up in his uniform – this is probably the genesis of the gay/flip flops/cargo shorts connection — but they will never look right. It’s like a Hasidic rabbi on a sailboat. Doesn’t work. Since the real thing is straight-only, the mystery only grows deeper to me by the day. These guys exude every stereotype of fratty heterosexuality: Intolerance, mediocrity, bodies that go to shit once lacrosse season ends. It’s the most intoxicating of all straight guy vibes.

I long ago stopped lusting after most straight guys. In my closet days they were the only ones I wanted, but I quickly realized that A) it was too much work and emotional trauma and B) Many straight guys stop looking good after college. The streets of Chicago’s Wrigleyville look like someone fed Carson Daly after midnight, and then got him wet. Not attractive. But no amount of logic or resignation can stop me from being sexually fascinated by the spawn of Cape Cod.

As a pretty easily-identifiable indie kid, there is nothing that I can immediately think I would have in common with a guy like this. In every period of my life, from braces-having nerd to high school closet fag to actual, out confident gay guy,  preppy guys make me feel like I’m in immediate physical danger. Which make me want to piss them off all the more with flirting. Which increases the discomfort on the other end, which just starts the whole cycle over. It’s terrible but such a great way to pass time. How subtly can you check out a preppy straight guy without them noticing? When you meet one, how affectionate can you be while still staying in the realm of friendly bro-dom?

Does anyone out there share my fascination? Understand that the second one of these guys turns out to actually be gay, the appeal is gone? The outfits seem forced, the swagger a defense and not the actual walk of entitlement. When I find out that “What the fuck do you want” glare is actually a hard cruise I die a little on the inside. The cracks show and this guy is no longer the thing I used to check out in the group showers in my college’s sports facility. He’s just another boring, disappointing person.

So I hold on to Kierkegaard’s definition of true faith, which is to believe that something will happen while also holding the unwavering conviction it won’t. So if I ever make out with one of these guys, they have to be gay enough to be interested while still retaining all the straight boy allure that makes them such a prized pig in the first place. If it happens, TNG readers, you will all be the first to know. I’ll be tweeting it from a poorly decorated bedroom in Georgetown.

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  • Topher said:

    I was crazy for fraternity guys in college. Then, I joined a fraternity and slept with a fair share of my bros. Does it make he healthier or far sicker than you that my strong attraction is undiminished when the fratty dude agrees to a little undercover action?
    Whatever the answer, I had to swear off the whole thing – things got a little too dicey in that straight/gay no man’s land.
    Doesn’t mean my head doesn’t still swivel when I see greek letters on a football jersey!

  • Jason Natalie said:

    Generally, I find the attraction similar to your description- a lustful intrigue that is dispelled by any actual interest. Being from a slightly divergent background then, what I would presume, a majority of these guys come from.. it’s difficult to associate or even fathom a functioning (cordial) “relationship”. Perhaps, as you also discussed, this interest is merely admiration- as they are imbrued by the few recognizable masculine/straight male qualities queer men unsuccessfully attempt to simulate.

  • Sir Lindsey Buckingham said:

    You’re certainly not the only one out there with this fascination. I’d venture to say that like 90% of homos feel this way. I absolutely did for a while. Until I met way too many-way hotter-straight boys with tats and tight jeans. Equally unhealthy for a skinny faggotron.

  • Blago said:

    “this breed of guy never comes homo.”

    So, correct me if I’m wrong, but you went to Kenyon for college, right? I know for a fact that when I went there (1999-2003) there were closeted gay (or bi-curious, or whatever) guys in frats who basically looked like your fratty fuck fantasies. None of them were out, but one of my best friends from college slept with a few of them. So it’s just not true that gays (or bi-curious guys, or whatever) can’t “come homo.” I bet those guys were right under your nose all through college. And if you need more evidence, the guitar/keyboard guy from Vampire Weekend is a homo and at least used to do that look pretty well (exhibit A: http://acontinuouslean.files.wordpress.com/2008/01/gq-vw-two.png).

  • Ruth said:

    Zach – teach me how to write like this. Also I loved that book, sort of. Have you read his diary of a seducer?

  • Jack said:

    The answer here is closety Georgetown prepsters & trust me there’s plenty to go around.

  • Cyrus said:

    Great Article Zack! Interesting to see how sexuality, attraction and beauty is greatly informed by fashion. Just as one can look “gay” through fashion, one can also look ” straight”- notably the backwards sports team baseball hat, a skateboards, board shorts, black sunglasses and there is a sort of erotic attraction to looking straight or heteronormative.

    While I disagree with “this breed of guy never comes homo” because I have seen a couple of guys that do pull this of, I agree with “but they will never look right”. Its another forefront for fashion to shape sexuality and vice versa. But subtract the fashion, Are we still attracted to same type of guy?

    As for myself, I can say I am attracted to the average looking guys who do fit a heteronormative dress. The unconspicuous, unbedazzaled, average looking, almost “hipster” fashion. But it goes soft the moment one announces their heterosexuality. Its hard for me to be attracted to a guy who i know I cannot be with sexually. But their dress has a lot to do with my initial attraction to them.

  • Matt said:

    I enjoyed this post quite a bit and empathize with the combination of lust/unattainability that these types exude. I have added this style to my wardrobe and think I can do it quite well… probably because I saw it every day in college (but was too radical a queer to have any in with these guys). One piece of advice gays who are tying to pull this look off… no cargo shorts! Fugly and fatty. And Cyrus, nice comment. Sometimes I wonder if I place too much emphasis on potential partners’ style of dress. In the end of the day, though, the look is a huge turn on.

  • Mitchell said:

    I find myself in agreement with your adoration of preppy boys. That being said, I don’t agree with your assertion that gay boys can’t pull this look off. My first pair of top-siders were given to me when I was in elementary school. I have been wearing Ralph since I was in diapers. My family has belonged to a country club forever and I also happen to be attracted to boys. I actually knew I was a preppy WASP way before I knew I was gay. The entitled attitude in which you speak of is something a person possesses based on their station in life; it rarely has anything to do with their sexual orientation. I just think that maybe the preppy gays you have met are faux preppies that have just tried to pass themselves off as the cultured elite. Being preppy is de rigueur for me, it isn’t something a person just decides one day to be.

  • Michael said:

    If you want real-life preppy boys who also like other preppy boys, visit Richmond, Charlottesville, the Hamptons, Charlotte, Atlanta, or the international (i.e. American) dorms at UK universities. The trouble is that they’re usually as mediocre and boring as their straight compatriots.

  • Eric said:

    I find I initially agree with the attraction trend here. Every time I see a boy dressed like that a grumble something negative, yet inaudible and glance at these preppy boys one more time before I imagine what cocky crap they’d say to me before I twisted their head off like a pop-top. The thing is, while my attraction to them physically lingers in the lime-light of sexual fantasy, I’ve never ever met a guy like that, that I could have a serious conversation with without disliking him for his idiotic, simple virtues: Always cocky, overconfident, and boisterously rude. If I had to hang out with that for more than 12 hours, I’d put a 124 grain 9mm Hydroshock into my head, or his. I don’t fit in with them anyway, so I usually just shrug it off as what it really is: A delusion of grandeur.

  • Jake said:

    I agree with this 100% as a masochist, these guys are perfect targets, they do homoerotic acts (frat guys) controlling, strong, and super hot! I can’t count how many fantasies I’ve had about these kind of guys. *drools*

  • Gerard said:

    I must either be super-stealth or really lucky…from days as a Sig Ep in college to
    my professional life I have been able to get them to unzip – enjoy their moment -
    and high five it later in the week. It IS good. Now get out there and practice.

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