They Lied: You Should Have Sex On The First Date

Dating is hard. We’ve heard that a million times. It often seems like those few people saying “dating is fun” are the ones who simply chose to turn over a new leaf rather than give up when the going got tough. There are rules: old rules, new rules, classic rules that are easily applied to the modern age of dating, and others… not so much.

One rule that we’ve all heard: never fuck on the first date. And sure– it sounds antiquated. But, that doesn’t mean it doesn’t echo in our heads when the time comes to hug goodbye at the end of the night or propose that things go further. Some dates happen like ordering an entree before that brownie that looks really, really good: you just do it, because it’s the way things are done, and you worry you’ll be judged if you skip a step. But, most people who don’t feel that way are looking for a partner. And, it’s strange looking through a barrel of single people for someone you’ll share some (or all) of your life with. It sometimes seems wrong to online shop for your other half the same way you do for a new pair of sweatpants, but it’s how you get a view of all the options. 

I went on my first “date” (in the classical sense of the term) at 25 after ending an 8-year-long relationship. My waiter at a restaurant had slipped me his number, and we went out for drinks the following week. The evening of our date, I told myself as I re-setting-sprayed my makeup and threw back a preparatory glass of pinot grigio that no matter what happened, I would not have sex with this man tonight.

On the sidewalk afterwards, we kissed in the street beside the Citi bikes and the traffic gently swooshing the summer air. I didn’t know much about dating, but I knew making out on the street was not usually the end of a night. I leaned into my warm tipsiness just enough to turn my promise to myself into what I hoped would come across as some kind of Manic Pixie Dream Girl exit.

I handed him my styrofoam cup of ice cream and whisked away without warning. The truth was no matter how 6’4 with muscular arms and great taste in wine (that I’d had many glasses of) he was, I still didn’t have any interest in going home with him. For this reason, I was thrilled I’d made a non-negotiable deal with myself. The truth was, I wasn’t worried I’d want to fuck this man; I was just worried I’d agree to it. When I got home, he texted me, “You’re cute.” Ah, I did it! I aced the date.

He and I went on some more dates. The sex happened eventually, and it wasn’t good. He wasn’t good either, and it ended after I invested a few months and had exactly zero orgasms. What followed was countless Hinge dates. They ranged from me making a plan to clock someone over the head with his own dumbbell in case he attempted to attack me to enjoying wine with a man who I’d have bet a large sum of money would never voluntarily fuck anyone who identified as a woman until he paid and said: “my mom says if you want to see a girl again, you pay.” I no longer needed to tell myself I wouldn’t have sex on the first date. I just told myself I wouldn’t have sex unless I wanted to. It sounds simple; it’s not. But, I mastered it. And no matter how many dates, hopeful Tinder conversations, or invitations at the end of the night I racked up, sex right after meeting someone never interested me. 

Another old saying about dating? “When you know, you know.” After applying a hefty dose of demystifying, I think this one is actually true. I took a date to my favorite bar. He lived outside of the city, and I was happy to show him Manhattan. We decided to go elsewhere to get dinner. I knew I didn’t want it to end, and we’d already beaten my record for most locations logged on a first date when we entered the second establishment. I suggested a third, and we went. I was many drinks in at this point, staring at his lips while they spoke. I had a sneaking feeling that the last train of the night out of the city had already left. I didn’t mention it; I didn’t want him to leave. “I’m not sure I should drink anymore,” he said. He was probably right, but I didn’t know the next move. I listed some options for things we could do next, burying “you could come back to my place” in the middle like it was no big deal. “Yeah, okay– let’s go back to your place,” he said. He later revealed that he knew the last train out of the city had already left, but he didn’t mention it, because he didn’t want to leave.

I didn’t think, at all, about whether I wanted him to come home with me. I just knew that I did. This notion that I could be screwing something up or putting myself in danger or ruining my chances with someone I liked was gone. It was simple, and I didn’t need to debate anything with myself then, and I didn’t when he made me cum that night, either.

He and I were in a relationship about six months later when I got a text from a friend. She was a good dater– probably the best dater I knew. She was one of those rare individuals who seemed to enjoy the process of dating. It seldom seemed to bring her down or make her worry about the future or doubt that the process was ever going to “work out.” She’d cracked the code we all pray to crack. She was a sex-on-the-first-date expert, and she kissed every date– even the ones she didn’t like, just to test it out. 

“I think I’m going to try not to have sex with this one,” she said about her upcoming date. She was tired of men thinking of her just as a fuckbuddy, and she wondered whether the age-old advice was true. I texted my boyfriend, “Why didn’t you decide you didn’t like me after I fucked you on our first date?” Strangely, it was the first time any self-consciousness about my own decision ever surfaced. He was confused, and I explained my friend’s conundrum. He replied:

“There are no rules.
Decide if you want to fuck someone and then do it.
Or don’t.
Who cares.”

I said yes, but he was simplifying it. Sure– we all want to reject old, patriarchal ideals, but does it really pay off in the end? He responded, “I’m confused, though. Why would fucking you on the first date make me NOT like you?” I paused. If sex is good, both parties probably want to repeat it; right? There’s a spark or there’s not; it’s mutual, or it isn’t. So many things need to fall into place to make a date worth repeating– let alone repeating a lot. And, if you feel them starting to fall into place, you should let them, whatever it means. I think, believe it or not, if your gut says the sex will be good, it will. If it says you should wait, you should. If it says you should block his number and report his profile on Tinder, you should probably go through with it. To quote my boyfriend of a year and a half who I fucked on our first date, “There are no rules.” When you know, you know.

Next Up, A Cop Caught Me Having Sex (And Saw Everything)