The summer after my senior year, I was in love. I was 18, she was 17. I took her to prom and I was getting ready to go to college, a thousand miles away. I felt like the luckiest guy in the world. I couldn’t just let her go. I had to—wanted to show her how much she meant to me.

I had never shown anyone “how much they meant to me”—at least not like that. I knew what I was supposed to do, and vaguely how to do it (thank you, Health class), but had never actually done it, so I didn’t know what to expect—except that I should have already done it. I distinctly remember, my freshman year, being admonished by a childhood friend (who I was actively growing apart from) that my “goal” should be to lose my virginity by 16. “Sixteen?!” I thought. “I’ve never had a girlfriend.” But 15 down, 1 to go before I was going to be an old sack, a lame duck, hopeless. I was a little relieved when the age passed without much fanfare.

All of that pressure, and all of those expectations came rushing back that summer. (Not prom night—not that cliché. Frankly, I think we were too pooped that night. But I remember her sweetly resting her head on my arm for the first time as we checked into post-prom. Pressure: +1.) Even with the support of my high school sweet heart (who was not a virgin) and a home-court advantage, I felt like I screwed it up. There were no fireworks or name-shouting or candles or Mai Thais or bare-breasted lounges by a jacuzzi. It was two kids flailing around on a bed—and I think that’s the way it’s supposed to be.

My timing was just about goldilocks. I can’t imagine swiping my V-card in college; there’s enough novelty and pressure waiting for you already. But I’m not sure the first experience can ever be goldilocks. Our culture has glorified (marriage), objectified (porn), and romanticized (Hollywood, grocery store check-out paperback novels) sex beyond recognition—and every teenager has to grapple with that or remain completely sheltered. Either way, they are naïve and clueless. Jerry Seinfeld says with sex, like comedy, you can do any as many flips and spins as you want, but you’re still diving into two feet of water. The only way to discover that, is to jump.