Q: I’m a recently divorced 40-something woman, now dating again, and I’m wondering what the guidelines are on how long to wait to have sex. I’m not interested in casual sex, but I have a healthy libido. If I’m really attracted to a man, I’ll be dealing with some powerful mixed (internal) signals regarding how long to wait. Really what I want is to have sex with a man I like as soon as reasonably possible without getting labeled by him (consciously or subconsciously) as an expendable floozy.
A: Tempting as it can be to tear off each other’s clothes and rut like wild animals on the first date, it can be less than conducive to a desire to meet up again to ask things like “So…where’d you go to middle school?”
Also, you do risk getting labeled a hussy for not keeping an aspirin clenched between your knees — Rush Limbaugh’s advice for unmarried women he isn’t popping Viagra for — while the date you drop the aspirin for gets to put another notch in his oar. As explained in previous columns, men and women are biologically and psychologically different, and the sexual double standard springs out of those differences — like how one sex gets pregnant and the other sex gets paternity uncertainty. As nice (and fair) as it would be if casual sex worked the same for women and men, there’s an old Arab saying quoted by a Lebanese-born friend of mine: “If my grandmother had testicles, we would have called her my grandfather.”
Some women do wait to have sex with a man they’ve just met — like, a whole hour — and manage to make that the first hour of the rest of their lives together. Just because that’s risky doesn’t mean it’s impossible. But, sleep with a man before you know who he is and you could find yourself wearing lust goggles — convincing yourself he’s good for the long haul when he’s really just good in bed. The good news is, men in their 40s tend to be less “use ‘em and lose ‘em” than those in their 20s. “The third date rule” — the expectation that the third date is the sex date — is also more of a factor for 20-somethings. If you’re, say, 45, and dating guys 50 to 60, the third date rule is probably something more like “Don’t fall asleep.”
When dating, remind yourself that the part of you that’s clamoring for sex is not the organ that does your best thinking, and plan your outings accordingly. Keep in mind that people who regret their behavior on dates tend to say stuff like “We got really drunk, and then we slept together,” not “We went to the museum in broad daylight and then had one too many lattes.” As for how long to wait to have sex, there’s no magic number of dates. But, since casual sex isn’t your thing, you should probably hold out until there seems to be an emotional attachment — on both sides. Maybe a good guideline is waiting until you and a man are kinda cuddly. Until that time, hint that your favorite sex position actually isn’t arms folded/legs crossed; you just like to get to know a man before you get to know how his Miller Lite chandelier looks wearing your thong.
Q: I’ve fallen for my new best friend, a woman I met two years ago while we were both going through similar divorces. Sometimes I think the attraction’s mutual. She recently started dating but hasn´t met anyone she´s into. I’m going crazy trying to decide whether to say something and risk losing the coolest friend I´ve met in decades.
A: The line from Cole Porter is “Birds do it, bees do it,” not “birds and bees get a committee together to discuss it.” Telling her how you feel could be icky and embarrassing if she doesn’t share your feelings — and maybe even if she does. You’ve heard of “plausible deniability”? If you decide to go for something with her, what you need is plausible drunkability. Have drinks with her, get a little fuzzed, and make a move on her. If she recoils in horror, it was the alcohol talking. If she kisses back or, better yet, is all over you like freezer burn on mysterious leftovers, follow up by asking her on a date. (Emphasize the D-word, reinforcing that your interest is more than friendzonely.) Sure, by making a move, you risk losing a friend. By doing nothing, you risk missing out on a lot more. Life is risk. You can either hide under your bed or opt for managed risk. That doesn’t mean managing risk out of existence; it means having a plan for damage control if things go badly. (“Captain Morgan, next time, you behave yourself!”)