When Should You Sleep with Someone?
by the Dating Diva
October 20, 2000

Dating would be so much easier if there wasn't all that emotion and analysis associated with sleeping with someone for the first time. When I was younger I would try to convince myself sex shouldn't be such a big deal. If I just pretended it was low-key than perhaps I could force it to really be low-key. It never worked. No matter how much logic you throw at the situation the fact remains that sex changes everything. Sometimes it brings you closer, sometimes it forces you apart -- but it's always something.

For the lowest impact on your psyche possible, you just have to make sure that first time is always as comfortable and secure as you can make it. I know of someone who says she knows the time is right when he's started using terms of endearment -- "sweetie" or "honey." I know of someone else who said if she'd share a cab with him, she'd sleep with him. (Well, at least it's a standard . . . ) Regardless of the standard, to make sure that first time leaves you with the elation it should, it needs to occur at the point in the relationship when you know you're ready.

Of course, that right point varies for everyone. Here follow some of the best standards I heard.

Helen: If I'd use his toothbrush, tell him I have cramps, let him see me in my usual alluring around the house outfit (no makeup, ponytail, boxers, and T-shirt), hear me sing . . . well, we're getting there. As far as timing, I figure once you know you have Saturday night plans without making any Saturday night plans is a good gauge.

Steve: Sober and recently schtupped, I'd say I'd only sleep with someone I was in love with. But if it's been a couple of weeks, and I've had a couple of beers . . . let's just say that new physics are involved, and time compresses.

Lindsay: What I'm interested in is towels. As far as I'm concerned towels say a lot about a man. I'm not interested in any guy who has some nasty set of mismatched, raggedy towels slopped around his bathroom that look like they are remnants from some set his mother gave him before he went off to college. If a guy cannot get his act together to buy a decent set of towels, he is not an adult and I am not interested.

Dee: I have to be at least somewhat interested in maybe having him as a boyfriend.

Sarah: I say as long as you are safe, and you are not hurting anyone else, and you are comfortable with it, and you know yourself well enough to know you'll still be comfortable with it after-the-fact, if it feels good, go for it. Life's to short to deprive oneself of simple pleasures.

Kelli: My last long term beau and I waited three months. I'm not sure why, it was hard as hell, but it seemed to be a good thing, we lasted about three years. My most recent boyfriend and I waited two dates, and that translated into a two month relationship doomed for failure. Hmm.. is there some spooky math coincidence here? Anyway, what it boils down to isn't a "thing" they do, or what they say, but simply how they make me feel. A guy who can take my breath away with a kiss, who isn't so pushy and forward and permeating sex, sex, sex, has a much better chance of "getting some" than one who does.

Jimmy: I'd like to think I'd wait a few dates, or even months to really get to know someone. Though sometimes I've hit that point pretty quickly and felt really secure with them. So I've slept with someone fairly quickly. I wouldn't judge the woman on how soon she sleeps with me, however. Having sex early on in a relationship is a choice I make as much as she does.

Susan: 1) as soon as we've agreed not to date others and I am convinced he's not lying, or 2) whenever I've had so much to drink I can't stop myself.

Some things which might help his case:

1) introducing me as his "girlfriend" to his friends and/or family
2) cooking me dinner at his home which had better be clean
3) asking to meet my parents
4) pretending not to despise my cat

Ann: My recently-created standard goes something like this: it's okay when it's not going to be a "transaction-by-transaction" negotiation. In other
words, when you start sleeping together you've actually started something that's going to continue until one or both of you decide that it's not, instead of just that you're sleeping together this one time, and then you might again later or you might not. That's the standard... it's application? Another story....

Michael: It depends on whether I want to see them again or not. If I want to see her again, I won't sleep with her. That's probably backwards, right?

Yes, it's probably backwards. But it also seems to be a fact that sleeping together too soon ends a relationship more often than does waiting awhile. So pick a standard -- feel free to steal from above -- and stick to it!