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A Gentleman’s Guide to the Halloween Hookup

1028KMT - HalloweenHookUp_Hed

Advice from certified ladyperson and expert on all things sexy and scary, Michelle Ong.

Halloween festivities can sometimes feel like amateur hour¬—all your favorite haunts (heh) are packed to the gills, “Thriller” is playing for the 36th time, and you can barely keep yourself from punching the guy in the Kim Kardashian costume.

And yet, every time this most hallowed time of year rolls around, we slap on the face paint, go dancing like it’s the Second Coming and flirt outrageously with someone dressed like a meme. Why do we do it? Because transforming into someone else—with the aid of masks, feathers and the rest of it—gives us license to act like somebody else. Even if that somebody else is a drunk Sharknado.

In other words, never doubt the extent to which an abundance of liquor and latex will allow you to really just... let yourself go. But while this is the best night all year for string-free liaisons, particularly when many members of the female species will be, uh, considerably more exposed than usual, you should always do your due diligence. Woe be to the pitiful gent who wakes up the morning after with the physical manifestation of regret sprawled out in his bed, spreading sweaty glitter all over his sheets.

Hence, your quick-and-dirty guide to the three types of people you’ll encounter while pursuing your Halloween hookup.

The Sexy ________

The girl: Anyone displaying her assets to the fullest extent, while missing one essential element: a real costume. In lieu of clothing, relies on props to identify the look she’s going for. Furry ears: must be a cat. Eye patch: (probably) a pirate. Giant pepperoni: congratulations, you have stumbled on the fabled and highly prized sexy pizza.

The plan: Shower her with the attention she craves. But don’t stare. Do not drown her in compliments. Don’t even use the word “sexy.” This is important. You’ll be one of a gazillion guys talking her up tonight, and ultimately, the one who stands out is the one who treats her as more than eye candy.

The risk: She gets scooped up by someone else just when you thought you’d closed the deal.

The reward: Living out your fantasies without having to even ask.

The Overeager Groupie

The girl: The one who spent way too much money on her costume. And is constantly trailed by at least five other girls wearing variations of the same costume. Making it that much harder to snag some alone time.

The plan: The Spice Girls once said, “If you want to be my lover, you’ve got to get with my friends.” This motto is now your mating call. Gain the trust of her BFFs, and you’re golden.

The risk: Losing sight of your target.

The reward: Fivesomes.

The Lazy Snob

The girl: She “forgot” to wear a costume. Or just admits to not caring enough to plan one.

The plan: Seduction by wit. Her lazy attempt to throw parts of her wardrobe together reveals one thing: even if she won’t admit it, she probably thinks she’s better than half the people at the party. Your charming quips will prove to her that you’re not part of that half.

The risk: Her cool air of ambivalence is just masking the truth: she’s really boring.

The reward: Not having to peel itchy, smelly fabrics off at the end of the night.