Miss Information: How Long Should I Wait to Sleep with Someone?

Pin it


Have a question? Email Letters may be edited for length, content and clarity.

Dear Miss Information,

I’ve been with a girl now for a year. She broke up with me in the middle of a double date this past weekend, and I ended up giving her cash for a cab, because I felt driving her home was out of the question. She says it isn’t me, but that she needs time to figure out who she is. I can’t help but think this is a lie, and she’s got eyes for someone else. How can I find out the truth? — Never-Saw-It-Coming

Dear Never Saw It Coming,

WFB, Never Saw It Coming. As in, “Why Fucking Bother?” Let’s say she does have her eye on someone else. In that case, what’s a lie to you is a gentle let-down to her — a non-confrontational way of giving you the boot without any ugly screaming matches, sobfests, or drama. Let’s take it even further and say that she is dating this guy and it started while you were going out. Would that bring you back together again? No way. It’d only drive you further apart.

Apart is where you need to be, Never Saw It Coming. Either because your ex-girlfriend is a lowlife who dumps long-term boyfriends in the middle of bowling dates or because there are some high-level shenanigans going on in this relationship and you are in triple-dog-deep denial. I don’t know which galls me more — the fact that she ditched you while out with your friends or the fact that you paid for her cab fare. You could have stuck it out and driven her home. She could have insisted on paying her own way or hitched a ride with the other couple. I don’t have your whole history — or her side of the evening’s events, for that matter — but the way it was handled speaks of bad decision-making and lack of impulse control. Are you the guy who wants to play savior? Do you get off on making others feel guilty? Is that why, despite her horrid behavior, you shelled out for her transpo? Maybe you’re so moody and volatile that she felt like she had to end it in public, lest you pull a complete and total freakout?

I realize all these explanations put you at fault, Never Saw It Coming, but that’s on purpose. While I’m open to the possibility of your ex being a piteous excuse for a woman, I’d like you to think about how you might have been a factor in what went down. Even if you come to the conclusion that you’re a total victim, lessons can be learned. Once you’ve done some reflecting, then you can ask your ex about the breakup. Keep in mind that infidelity accusations will probably net you a loud hangup after a ten-second discussion.

To be honest, I’d prefer you abstained. Exes have their own identities and agendas that they’re sorting out. They’re a piss-poor source of objectivity, not some mystic Oracle. The search for post-breakup answers starts and ends within ourselves.

Dear Miss Information,

How long is appropriate to wait before having sex with someone new? I’m pretty inexperienced — I’ve only had sex with one guy a few times. It was someone I liked and trusted, but I mostly went for it because I was tired of being a virgin (though, predictably, I still ended up hurt when we stopped seeing each other). I’ve dated casually and hooked up with a few guys since then, but I’ve never felt comfortable enough to have sex.

Recently, I went on a few dates with someone over a couple of months, and we were close to having sex when I put on the brakes. I liked him, but I didn’t quite feel the chemistry — we spent the night cuddling and talking instead. After that, though, he never called, and I’m not sure if I dodged a bullet. I would’ve been devastated if we had sex and he then didn’t call, but maybe I drove him away? What do you think? After how long (three dates? three weeks? three months?) would a reasonable person start to question whether I’m still worth pursuing? —
Call Me Old-Fashioned

Dear Call Me Old-Fashioned,

I’ve always found it interesting how the less sex we have, the more we let it color our every interaction and thought. It becomes the reason why relationships succeed or fail, when the truth is it’s just one drop in the big, constantly-leaking, heart-shaped bucket.

Take, for example, this first guy. You say you “ended up hurt” when you stopped seeing each other. As opposed to what? Girlishly exuberant? Frolicsome? No one feels good coming out of a breakup. Sure, the loss of your virginity might have been a contributing factor, but you would’ve been bummed out even if you hadn’t given up the goods.

This second situation has even less to do with sex than the first. You go on a few dates with minimal chemistry, then wonder if you somehow “drove him away” by not doing the dirty. Here’s another explanation: a couple of outings over a couple of months doesn’t indicate much interest on either of your parts. To think that this guy is not picking up on your lack of attraction would be foolish. We may use iPhones, buy soy milk, and drive hybrids, but at base-level we’re all just a bunch of hormonally-driven hairy mammals. My guess is he was feeling so-so about you as well, either because he picked up on your ambivalence or he had some of his own. He might have called you if you had sex, but he might not have, either.

In your question, you throw out a tidy series of numbers, but this is more of an essay question than a multiple choice. My advice is: do your homework (i.e., get to know someone); keep the bullshit to a minimum (i.e., know what your position is and communicate it clearly); and hope the odds are in your favor (i.e., love is an inexact science).

Readers, how long do you wait before sleeping with someone? Do you have a set rule that you always follow, or does it vary from person to person?