How Do You Know When It’s Okay To Sleep With A Guy

When Do You Sleep With A Guy

Among life’s greatest mysteries, we have a few recurring themes. What is the meaning of life? Why can’t I apply mascara with my mouth closed? And most importantly, how long should I wait before sleeping with a guy? Even in this modern day and age where everyone with a uterus and a Wifi connection is piping in that “women can do whatever the fuck they want. It’s no one’s place to tell another woman how to live her life,” the ideology remains: but he’s still not going to take you home to mom and dad if you sleep with him right away.

And so we’re left with an unanswerable question: how quick is too quick, and how long is too long? You certainly don’t want him to decide you’re “not wife material,” but you don’t want to hold off so long that it might feel weird to actually get physical. After all, you might not want to buy the cow if you’re getting the milk for free…but you also don’t want to buy a cow that doesn’t produce milk, ya know? But what if…maybe, just maybe, there’s no magical number of dates that will “make” a guy fall for you. What if we’re treating this as a major piece in the game of life, and it actually holds no significance? What if when you have sex doesn’t fucking matter?

Four years ago, my friend went out to a bar in her new city. She drank, and she drank, and she drank. Then she met a boy, and she drank some more. They talked, and flirted, and she made him her bar boyfriend. Things, seemed to be going swimmingly. Eventually, late into the wee hours of the night, she made out with him. Making out turned into a shared cab ride (#TBT) home from the bar, which — you guessed it — turned into full blown penetration. Four months later, her bar boyfriend was her real boyfriend. Ten months later, he told her he loved her, and just this July, I gave a bomb ass MOH speech at their wedding.

Conversely, another friend of mine had a crush on a boy when they were in school. She analyzed every text message and played everything exactly right. They progressively hung out more and more, until she was a shoe-in for every date party. After more than a semester of their pseudo relationship went by, she finally decided to sleep with him after formal. The weekend passed, and she never heard from him again.

You might say both of my friends are just exceptions to the rule. But I’d argue your rule is irrelevant. The simple fact of the matter is that the guy who went on to marry my friend who should have been a one-night stand, simply put, just liked her. She made enough of an impression on her, and they vibed well enough that he wanted to see her again. And the guy who ghosted after finally getting what he wanted? He didn’t like her. At least not enough.

That’s the only thing that will determine whether a guy is going to stick around after sex — his feelings for you. He’s not going to think you’re the love of his life, then change his mind once he gets his D wet, unless you have some serious stankpuss. If he likes you enough, he’ll want to keep seeing you. And on the flip side, a guy isn’t going to magically fall in love, just because you “played your cards right” and held out as long as you could. The sex doesn’t matter. If sex is his end game, it’s always going to be his end game, no matter how long you wait. And if he likes you, he’s going to keep liking you, no matter how quickly you hop to the deed.

You can wait as long as you want. It’s a good test to figure out if he likes you, because guys won’t stick around forever if they’re not into you. But at the end of the day, when you decide to do it is not going to influence how a guy feels about you. The only thing that can influence that is…well, you.

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Veronica Ruckh

Veronica (@VeronicaRuckh) is the Director of Total Sorority Move for Grandex, Inc. After having spent her undergraduate years drinking $4 double LITs on a patio and drunk texting away potential suitors, she managed to graduate with an impressive GPA and an unimpressive engagement ring -- so unimpressive, in fact, some might say it's not there at all. Veronica has since been fulfilling her duties as "America's big," a title she gave to herself with the help of her giant ego. She has recently switched from vodka to wine on weekdays. Email her at

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