What I Learned From 10 Years of One-Night Stands

I waited until college to lose my virginity, an overwrought decision I made with my long-term conservative boyfriend. We practiced safe sex for a few months, and then the relationship fizzled around the same time as my conservative Protestantism. I completed my undergraduate education with a string of whiskey-soaked hookups, with that dramatic song that often finds its way into cell phone carrier commercials blaring in my head: “Freedooom, freedooom, talkin’ ’bout freedo-o-om!”

I figured I’d settle down shortly after that, but instead, I entered a decade of mini-relationships, casual flings, and plenty of one-night stands. Today, my partner count is higher than my age, but I have zero regrets—rather, I’m brimming with knowledge about what works for me in bed, not to mention a heap of great stories, like hotel sex with a C-list celebrity and my night with the visiting Tantric practitioner.

What I don’t have: STIs or any unintended pregnancies! Proving that, aside from any messy emotional stuff, behaving like what less-evolved humans would call a slut can be consequence-free—as long as you’re safe. But in addition to the obvious sex-ed stuff—get the HPV vaccine, always use a condom, get tested on the regular—I’ve learned some valuable sexual health lessons from the notches on my bedpost. Here, some hard(ha)-earned wisdom about safe sex. (For another woman’s take, check out Sex Advice I Wish I Knew in My 20s.)

Partner #3: Demanding safe sex is YOUR responsibility.
“Why don’t you trust me?” is an actual thing an actual, regular hook-up said to me, in a frustrated tone, whilst trying to convince me we didn’t need condoms now that we’d been sleeping together for a few weeks. Which is insulting, obviously, but also baffling: Why should he trust me? Shouldn’t he be concerned that I could unknowingly give him gonorrhea, which would lead to swollen testicles, gross discharge, and pain while peeing? (Note: Here’s How to Talk to Him About Your STI Status.) This was an important life lesson: Like walking home alone at night, STDs are just not as terrifying to (many) men as they are to women. (Fair: Symptoms are generally less debilitating and more easily treated in guys, plus it’s easier for us to lose our fertility.) Bottom line: You need to be the one looking out for your own sexual health.

Partner #20: If he hates condoms, he might just be wearing the wrong size.
This guy begrudgingly wore condoms because he didn’t, in fact, want either of us to die (reminder: STIs literally can kill you), but he would always grimace when it went on and complain about how they made him lose wood. Homeboy was 6’4 and well-endowed, yet he had never considered that maybe condoms felt like too-tight rubber bands because they were, in fact, too tight. He was wearing the wrong damn size. I made him pick up Magnums and became his new favorite sex partner ever.

Partner #1: Good guys understand that birth control is a shared burden.
Back in the days before health insurers had to cover the pill (#gobama!), my oral contraceptives cost about $30 a month—kind of a lot for a poor college student. My then-boyfriend, recognizing that an accidental pregnancy would involve us both, would split the cost with me. Similarly, I always expect guys to buy their own condoms and have them at the ready in their apartments. Condoms are expensive and, unlike Carrie Bradshaw in the pilot, I don’t feel an obligation to carry a string of them in my purse. That said…

Partner #14: Carry a condom in your wallet.
Just keep an eye on the expiration date, and occasionally give the package a squeeze to make sure the bubble of air is still in there (that means it’s sealed). Oh my god, that was great vacation sex. (P.S. Epic Vacation Sex at Home is possible!)

Partner #9: Always pee before and after sex. Always.
One particular gent really enjoyed cuddling—so much so that when I tried to get up to tiptoe to the bathroom, he playfully pulled me back down, locking me in those big hot muscular arms. I went with it, but let me tell you, I really came to regret not flushing out the bacteria pushed up into my urinary tract.

Partner #26: Disclosure isn’t a sexual death sentence.
I was half-naked in bed with a new guy I really liked, one I could picture myself dating and potentially getting serious with. “I have something awkward to tell you,” he said, sitting up. “I’ve never had any symptoms but I tested positive for herpes. I’m on medication so it’s really hard to transmit, but, yeah.”

We didn’t have sex that night because I wanted time to chew it over and do my own research. And yeah, I was a little freaked out, but I also really admired the respect and honesty he showed when he could have just not told me. A few weeks later he turned out to be a total jerk, but hey, at least we didn’t break up over his herpes.

Partner #4: Your pharmacist is your friend.
One supremely hungover Saturday, I was waiting in line to pick up my birth control—I had to start a new pack the next day. In that groggy, sludge-like way, I was trying to piece together exactly what had happened the night before: I’d woken up with an equally hungover bro in my bed and a condom wrapper on the floor, but I wasn’t positive how it all had gone down, which is especially nerve-wracking considering I was at the tail end of my no-pills week. Did I need to see a doctor? Who’d see me on a Saturday, anyway? (Is this one of the 13 Questions You’re Too Embarassed to Ask Your Ob-Gyn?)

Then I reached the front of the line, and a lightbulb went off: pharmacist! A consultation desk! I could ask this nice lady if she thought I needed Plan B or not! In that case, she said no and had me just pop the Saturday pill from the end of my new pack for extra insurance.

Author Since: Jul 26, 2018