ADVICE 17: Can My One-Night Stand Become Something More?

How do I know that he's not just looking for sex? I fear that he is only interested because we had that one really fun night together. What do you think?
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(Questions have been modified for space and clarity.)

There's a guy with whom I had a one-night stand eight years ago. He recently found me on Instagram, and now we are talking about going out and how we always were drawn to one another. We were in our early 20s when we first met through mutual friends, but we never really knew each other. The way we are talking now, he seems like a really sweet and sensitive guy. How do I know that he's not just looking for sex? I fear that he is only interested because we had that one really fun night together. What do you think?

He's definitely interested because of that one really fun night together. What else would have made him reach out? That's his jumping-off point. You didn't know each other very well eight years ago, and you hadn't been in touch since. Your one-night stand is the reason you're hearing from him.

Of course, that doesn't necessarily make it the wrong reason. For one, physical chemistry is critical to any romantic relationship. It gets a bad rap, but that doesn't make it any less important. Call me shallow for saying so, but you have to be attracted to your partner.

Yes, it's secondary to things like trust and respect, and yes, it will fade if it's not supported by a deeper emotional connection. But it's still the primary differentiator between friend and boyfriend. So knowing that the two of you are compatible in that way should count in his favor, not against him.

I get your hesitation, though. To this point, your relationship consists of little more than one night of sex. He got it from you before, and now he's looking for it again. Plus, he's a guy. Your thinking makes sense.

The way I see it, deciding whether or not to go out with this guy is no different from deciding whether or not to go out with any other guy. There's always the risk that the other person is driven by motives you don't share. Finding someone who's on the same page and wants the same things, it's arguably dating's biggest challenge.

So why not give this guy the benefit of the doubt? Sure, he could be putting on an act. He could just be in it for sex, and if/when he gets it, you might never hear from him again. That's a legitimate risk.

But couldn't you say that about anyone else you might meet?

Besides, even if sex is his only motivation now, that doesn't mean it will always be. It's possible that once you start hanging out, his mindset could change. You really could have that deeper connection he mentioned, and all you needed was for the physical connection to bring you together.

That sort of thing happens all the time. Two people start out as friends, only to have it grow into something more. Couldn't your relationship blossom in a different order?

There's only one way to find out, and that's to give it a shot. And this is as good a dating situation as any on which to roll the dice: He appears to be a sweet and sensitive guy; you're physically compatible with him; and his sanity has been semi-validated by the fact that you share mutual friends. (You would have heard from somebody about any psychotic tendencies after sleeping with him, right?) What do you have to lose?

Eight years ago, the two of you had a one-night stand, then never spoke to each other again. And unless you're not telling me something, it's not like you pursued him or waited for his call, only to have him blow you off. He's shown no indications of being a jerk, which puts the two of you on equal footing for the moment. If you're interested in him for more than just sex, isn't it possible that he feels the same way?

COMING WEDNESDAY: Should I Have Fired the Babysitter?

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