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How To Make A One-Night Stand A Little Less Awkward

Your ideal casual-sex scenario probably goes a little something like this: you and a seriously hot stranger or friend with benefits rip each other’s clothes off, bang out a couple orgasms each, then part with good feelings all around. If only it were that easy. Given that 41 percent of people in a recent Adam and Eve survey said they have casual sex, there are a lot of chances for things to veer from that fantasy and slide straight into cringe-worthy territory. Here, experts explain how to navigate any weirdness that comes up when you’re giving casual sex a go.

You Want to Sleep Solo
Maybe you’re more than fine with sharing an orgasm, but sharing a bed? Nah. Whether the action is going down at your place or not, there are polite ways to either make your escape or get him to leave without offense. “Bring it up before the sex happens,” says Jane Greer, Ph.D., New York-based marriage and sex therapist and author of What About Me? Stop Selfishness From Ruining Your Relationship. “Explain that you need a good night of sleep and wanted to let him know ahead of time.”

As for why you need that quality shut-eye, you can explain that you have a lot to do the next day, you’re meeting a friend for breakfast, you have a doctor’s appointment early the next morning…you get the idea, just use good judgment. You don’t want to lie about needing to let the dog out only to wind up dating and having to come clean about that just being a furry figment of your imagination.

A different (yet just as potentially awkward) take on the situation is if he’s the one who explains why he has to split immediately post-O. Your reaction could be a clue that casual sex is stirring up more emotions than you’d care to deal with. “If you’re really in it for casual sex, it shouldn’t matter,” says Sadie Allison, Ph.D., the founder of TickleKitty and author of The Mystery of the Undercover ClitorisOrgasmic Fingertip Touching Every Woman Craves. “If you find yourself feeling insecure or like you’re about to get used, you probably shouldn’t be doing it.”

His Boner Is M.I.A
You’re in bed, hands are roaming everywhere, and you’re both panting like you just wrapped up a marathon. Only one problem: There’s nary a twitch below his belt. Instead of worrying that something’s wrong with you, chalk it up as one of the many ways penises can be so mysterious. “All guys have times when they can’t get an erection, whether it’s from nervousness of being with you or some other reason,” says Allison. You can say something simple yet cheeky like, “It’s no big deal, we can have fun in lots of other ways,” then proceed to show him exactly what you mean. Allison suggests warming each other up with massages, having him go down on you, or giving a hand job a shot.

You're Worried About STDs
First things first: Good job for caring about safe sex. It might seem like bringing up your STD status is the least-sexy thing on the planet, but really, taking control of your health is a pretty grown-ass woman thing to do. Ergo, it definitely means you’re an empowered, smart, sexy person. But still, the awkwardness can persist. “Making it playful can take some of the discomfort away,” says Allison, who suggests whipping out one of those trusty safe-sex adages like “no glove, no love” with a smile that shows how much fun will be had once the condom’s on. You can also be more straightforward about it and explain when you were last tested and what the results were—then ask him to share. If he gets all shifty or wants to forego protection, take that as a cue to call it off.

The Sex Isn’t Doing It for You
The safe-sex conversation went off without a hitch, his penis is hard enough to shatter glass, and you’re going at it with gusto. Only one problem: You’re pretty sure he’s mistaking your inner thigh for your clitoris, or he’s jackhammering you so hard you’re worried he’ll drill you down into the core of the Earth. “How you handle this depends on how nice you want to be,” says Allison. “If he’s trying and you feel bad but you know this is the first and last time you’ll have sex with him, you can do what you need to so he has an orgasm.” You’re also well within your rights to press pause, excuse yourself to the bathroom, then emerge with an explanation about why you need to leave to go to your place or why he needs to go back to his—like that you suddenly don’t feel well. If that’s what makes you most comfortable, go with it.

If you’re feeling bold and entitled to a good time in bed, as you should, give him some direction. “Take responsibility for what you like and educate him,” says Greer. That can either be through talk, like explaining how you’d like him to touch you, or just picking up his hand and showing him instead of telling. “If he does’t respond or follow through, you can move on,” says Greer. But if he’s eager to learn, that can mean lots of happy no-strings-attached sex in your future.

You Fall for Him, or Vice Versa
This is a real risk when engaging in casual sex. If you chance upon someone who makes your every orgasm feel like a 4th of July, you might end up fully dickmatized. “You have to address it somehow, or it can get out of hand and cause you a lot of pain,” says Allison. One option is to extricate yourself before you get in too deep, but sometimes it’s impossible to do that without knowing if he feels the same way. “You can bring it up and ask what happens if either of your feelings started to change,” says Greer. “Don’t make a bold declaration, just tease the subject to get a reading on whether he’d be receptive to something more serious.” You could also suggest something a little more couple-y than you two are used to, like grabbing dinner before your usual Friday night hookup. “That’s a clear way to send the signal that you’d like to spend more time with him,” says Allison.

Now, if the situation is reversed, honesty is the best policy. Be upfront if you’re only interested in keeping it casual. “Explain that you’re very flattered but that you don’t share those feelings and maybe it’s time to no longer see each other,” says Greer. After you talk about it, he may decide that he still wants to keep hooking up even though he’s catching feelings. If your gut says he’ll wind up heartbroken, you can stick to your guns because it’s evolved into something you didn’t expect. But if you want to keep at it, at least you know you aren’t leading him on.

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