One Question You Could Ask a Sex Partner That Could Improve Your Sex Life

“OMG, Emily…can you please write an essay about that?”

I was sitting in a slouchy wine bar with some lady friends discussing a guy I had just started dating. Although the group raised some potential red flags (Yellow flags? Pink flags? Flags at half mast?), there was unanimous agreement that the question he’d posed the night before was the best getting-to-know-you-sexually question any of us had ever been asked.

“That is THE question,” said one friend, gripping my knee for emphasis. “Why doesn’t everyone ask that question?”

Can I write an essay about THE question? Why yes, yes I can, but let me back up.


Six years ago, I had recently graduated from having the kind of sex where I just did the things I thought were “normal,” the things I thought everyone else was doing, and started to get weird. Not weird weird (though power to you if you’re weird), just specific, unique, personal.

The “normal” stuff was genuinely fun and pleasurable, but in many ways it still felt like going through a prescribed set of someone else’s motions. I wanted sex to feel special every time. Not Lifetime-bed-of-roses special, but like no two people had ever done that exact set of things with those exact words to that exact tune of giggles and groans. Special.

I was smart enough to know that to find that kind of special on the regular, I couldn’t count on chance. I knew I had to work for it, to earn it by being open-minded and honest. But the first time I had the chance to try, I quickly spotted the hole in my plan:

“So,” I asked, “What are you into?”

“Into?” he replied, “What do you mean?”

“You know,” I said, “Like…what do you like?” I was ready with my responses; I wanted to get into the juicy, the nitty-gritty, the delightfully surprising or surprisingly delightful stuff. I was ready to entertain any idea, even if I ultimately didn’t roll that way, because I wanted all of my ideas entertained.

“Um…sex?” He answered, the question mark in his voice reflected by a quizzically raised eyebrow. He nodded emphatically, “Yeah, I like sex.”

If I could have face-palmed, I would have. Bro, you’re giving me nothing to work with, and now you’ve made it super strange if I unleash a torrent of specific preferences.

It’s been a few years since that first failure of a conversation and I’ve gotten progressively better at both picking partners and easing into the dialogue I want to have. I’ve found that sharing first can make my partners feel comfortable, and that some people prefer to stick with the “normal” while they get their bearings, and get into the special later. As always, all that matters is that you and your partner are on the same page.

As for me, I don’t want to waste any time. If I’m here and I’m in it with you, I want it to be good from the get-go. Good doesn’t have anything to do with size or duration or superficial shit like that. For me, good means that you are in the moment with me, that you respect my desires as worthy, and that you pay attention when I express myself verbally and non-verbally. And I, of course, will make every effort to do the same for you.

So what was the magic question? What did he ask that leapfrogged us from normal to special?

“How do you get yourself off,” he asked, “when you’re all alone?” I get goose bumps just thinking about it.

First, the question acknowledges that I am a sexual being even when I am not in his presence, or in the presence of any other man. I am the agent, not the object.

Second, it is open-ended enough for me to respond however graphically I want. If I want to detail porn or toy preferences, I can. If I’d rather show him physically for him to mimic, I can. If I’m more comfortable keeping it vague (in the shower on Tuesdsays?), this question allows for that too.


For some people, this question will seem too invasive. Maybe you like one thing with partners and something else entirely on your own. Maybe building a Chinese wall around one corner of your sexuality allows you to guard it for yourself. I respect that, I really do. Like they say on How I Met Your Mother, there are plenty of reasons people choose to have sex. This question allows for that, too. “When I’m alone, I….” you can say, “But since you’re here, why don’t we….”

You know the best and worst part of the story? I realized as I was writing this essay that I’d neglected one crucial thing: He asked me, and I told, but I didn’t ask him back! I texted him, apologizing for my faux pas. He replied, “There’s always next time.”

Role Reboot regular contributor Emily Heist Moss is a New Englander in love with Chicago, where she works in a tech start-up. She blogs every day about gender, media, politics and sex at Rosie Says, and has written for Jezebel, The Frisky, The Huffington Post and The Good Men Project. Find her on Facebook and Twitter.

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