What To Wear When You’re Meeting Someone For A Casual Encounter On Craigslist

Even if we’ve never actually gone through with it, I’m sure many of us have read the Casual Encounters section on Craigslist. How can our curiosity keep us from it? It’s not only a look into how people behave when they can hide behind the walls of the internet; it’s also a chance to see what efforts (or lack there of) people will go to get laid. For the most part, the ads tend to be not just sexually explicit; they also introduce us occasional readers to fetishes that we didn’t even know existed. Why, yes, there is a man in Queens who just wants to come over and casually sniff your dirty underwear. And yes, you just sent that link to all your co-workers because you have nothing else better to do with the last hour of your workday.

There are, of course, those who have the desire to fulfill a fantasy they may not be able to communicate to their partner, so they feel safe in the anonymity that comes with sniffing some stranger’s undies. And then there are those who straight up want to fuck. There’s a world of orgasms to be had, and they want to pick the ripest one from the tree and enjoy it with someone besides their hand or battery-operated best friend for a change.

Casual encounters go way past online dating. There is no bullshit to cut through and before you even set up a place to meet, you’ve already laid down exactly what you want to do and you didn’t even have to make small talk over a shared appetizer. You’re going to score; end of story.

But how does one broach the Casual Encounter scene with the skill of a seasoned regular? Is there a technique? Is it an art form? Can we at least get a how-to handbook on the topic? My friend, who’s been doing this “thing” for a while now, gave me some tips as to how to present myself if I were, hypothetically speaking, going to make the rounds on Craigslist. You know, just in case I’m craving to be banged by a stranger tomorrow afternoon someone around the time I usually have tea and crumpets.

Pretend it’s Opposite Day. You’re not looking to date this person; you’re looking to fuck them NSA-style then leave. If you’re usually preppy in your attire, go hipster; if you’re normally a t-shirt-and-jeans type, wear a suit. This should actually carry over into your hairstyle and bags, too. Yeah, we all have a Strand tote bag, but on this night, you all of a sudden have a backpack instead! You’re playing a role, and that role is someone who’s on a mission to get laid.

Play into the fantasy. If the email banter between you and your new buddy has suggested things like thigh-highs, a jock strap, or a studded collar, live up to it! Show up entangled in a leather whip and nothing else if that’s what you promised. It’s not just Opposite Day; it’s about sticking to your guns and not disappointing the games that are about to take place.

Avoid wearing anything sentimental. This is a very important piece of advice. If you have an article of clothing or a piece of jewelry that has a deep meaning to you, make sure you leave at home. Let’s be honest—you are putting yourself on the line to get some, and if something should go a bit unplanned, you don’t want to not be able to wear you grandmother’s pearl necklace again just because the guy you fucked gave you a pearl necklace of his own all over it. You’ll never look at grandma’s gift the same way again, and you don’t want that.

Remove your heart from your sleeve before heading out. As with all NSA situations, sex is sex and love has no room in the equation. While a lot of people go out to screw not long after a break-up as a means to somehow move on, it’s important to remember emotions should be kept in check. If you’re someone who constantly wears your heart on your sleeve, leave that shit at home. Pin it to the towel in your bathroom and you can put it back on when you get home—after you’ve showered off that aforementioned pearl necklace.

Wear comfortable shoes. Why? Because you never when you may end up with a Ted Bundy or Aileen Wuornos on your hands and you’ll have to run like hell. But hey, that’s the risk you sometimes take when going the anonymous sex route. Although, statistically speaking, you probably have a better chance of being hit by a cab than ending up in 100-gallon drum of acid, but proceeding on the side of caution is never a bad idea. No one wants to go down at the hands of a serial killer for the sake of an orgasm they could have achieved at home with some wine and a Bernardo Bertolucci film.

Follow Amanda Chatel on Twitter.

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