If you want a relationship, that is; if all you want is a one-night stand, by all means, drop trou.
Any rule about dating is probably a bad one.
Yes, there are the rules that are obvious for the sake of safety: use protection, meet for the first time in a public place, etc.
But I find that when one follows an official set of rules — like those laid out of in the aptly titled 1995 mega-seller The Rules — it reduces finding a partner into something like passing the bar exam or performing a Beethoven sonata or installing a new water heater: something you get right mostly through rigorous memorization and adherence to a set of standards.
And most rules people create for themselves (outside of those that stem from a reasonable compatibility issue) tend to be the result of residual bitterness. I know a woman who doesn’t date creative types because of a few sour years of financially supporting a deadbeat wannabe writer (no, it was not me) and a man with a stipulation against teachers because the schoolmarm he dated said she couldn’t suck his balls with the same mouth she used to recite the ABCs. While it always feels empowering to learn from a bad experience, this approach is short-sighted because it judges a new person by the actions of the last one with the same gender.
But there is one old maxim I adhere to: No sex on the first date.
I bring this up because there is a new book that portends to be an anti-The Rules of sorts: It's Okay to Sleep with Him on the First Date: And Every Other Rule of Dating Debunked, a team effort by Andrea Syrtash and Jeff Wilse, two of the relationship “gurus” that get constant invites to news-lite programs like “The Today Show.” Like me, Syrtash and Wilse aren’t big on rules. Women should downplay their professional success? “In the most recent study, in 2008, male participants ranked intelligence as one of the top five attractive qualities out of 18 a woman can have,” says Syrtash. Let the man pursue? “If she approaches me and initiates contact? Great. There is no part of me that thinks, consciously or subconsciously, ‘Hmm… she’s hot … but I would like her more if I had to work harder,’” writes Wilse. Nice guys finish last? “Kindness consistently ranks as one of the most important qualities one seeks in a potential mate,” says Syrtash.
The centerpiece of the book is a rebuttal to the maxim about no nookie on the first date. “Putting arbitrary timeliness around intimacy makes most of us live in our heads and takes us out of the experience of being with someone and letting our connection unfold organically,” says Syrtash.
While I agree that there is nothing intrinsically harmful about boffing someone you just met (with protection of course), I think it’s best to keep clothed until you at least sorta know them (if you want a relationship, that is; if all you want is a one-night stand, by all means, drop trou).
In my experience, sex on the first date either uncomfortably accelerates a relationship or leads to discomfort for the woman who thinks she might have fallen into the “fuck buddy zone.” Yes, there is still a vicious double standard in which some men consider a woman not girlfriend material for unzipping early, even though, obviously, they unzipped just as early. Even if the man doesn’t adhere to it, the woman is at least aware that this kind of ape thinking cycles through some men’s mind. And if she doesn’t know the man she just slept with very well, she might think it’s cycling through his, leading to awkwardness. I’ve experienced both these scenarios.
A few years ago, I went on an afternoon hike for a first date. Once we had circled the nature reserve, we decided to keep hanging out, which led to dinner, which led to us awkwardly trying to find a workable sexual position on her futon. A few days later, I ran errands and my cell phone ran out of juice. As soon as it was recharged, I saw a barrage of text messages from her. “Where R U?” “R U OK?” Shit, we had, within half a week, come to the point where six hours without contact was a cause of concern. In three weeks, I was deflecting talks gauging my interest in kids. In six weeks, we were in a messy, shouty breakup. It probably never would have worked, but I feel like if we had moved more slowly, it would have at least been less messy.
More recently, I dated J, and I should say upfront I really liked her. She was smart, sweet and articulate. She was also a writer and the kind of girl who melted into laughter at a good joke or a funny story. The first date was the usual dinner-and-drinks combo and it ended the kind of kiss that shoots energy right down your spine and into your crotch but nothing more. Then I rushed things.
On the second date, after dinner, I asked her, “Do you want to see something unusual about this neighborhood?” She said, “Sure.”
I hid a bottle of wine in a backpack and escorted her to one of the most beautiful places I know: a round slab of concrete on the edge of the Allegheny River, leftover from some torn-away structure from Pittsburgh’s industrial past. Believe it or not, this piece of urban ruin is an aphrodisiac. It gives an awe-inspiring view of the city’s knockout skyline and, given that it is known to only a handful of locals, kayakers and riverside-camping gutter punks, chances are you will be undisturbed there. At sunset, I’m guessing it is the greatest make-out spot in the entire Rust Belt.
J smiled widely at sight of the city retiring for the day under an orange sky. I let out a small laugh.
“What?” she said.
“I don’t know why you have all those glum author-on-a-book-jacket photos on your profile because you light up when you smile.”
Cue the uninterrupted four-minute saliva exchange. Cue the hands everywhere. It got dark and we went back to my place and were soon on the couch doing more of the same.
“I don’t know what I should do,” she said, nervously.
“Do whatever you want,” I said.
She stayed on my lap.
After a few more minutes of this, I kissed my way from her neck to her ear and whispered, “I want you” and led her into the bedroom.
Twelve hours later, she sent me an email saying, “I feel like last night was too much too fast. I was absolutely a willing participant — and I enjoyed myself immensely, as you could probably tell — but I wasn’t as ready for it as I believed I was in the moment. I know you’re not pushing for anything further, but the problem is, I don’t know how we dial back from here. Or if that’s even possible.”
I tried to get her to reconsider. “I'd made a bunch of promises to myself that I'd been pretty good about,” she said, “but that night with you, though it felt great, felt like a broken promise.” I could read between the lines. She didn’t want to slip so easily into a man’s bed because she had decided that wasn't how she wanted to approach new relationships. I sent a message or two trying to convince her I sincerely felt something for her. I did really like her. I wish I would have paused and been satisfied with just liking her instead of seducing her. And every time I go on a dating website and breeze past all the interchangeable profiles and rude-seeming shitbirds, I realize how special she was.
So, now I save the romantic riverfront stone for the third or fourth date.
I wish hopping between the sheets didn’t have so many possible implications behind it, but it does. I think it’s best avoided for a date or two as you navigate the already awkward business of evaluating a stranger for the role of the most important person in your life (again, if that‘s your overall goal for dating). Our sexual politics are too complicated to go without this one guideline.
The no sex-on-the-first-date rule, if you'll pardon the comparison, is sort of like the Farm Bill. Every year, Congress passes an agriculture policy that holds up the country’s food supply with price controls and subsidies, the overall plan of which hasn’t been reevaluated since the 1930s. It’s hopelessly outdated but necessary until we sit down and come up with something better.