An awesome question: how do you ask to try something adventurous, without freaking out a new partner?

Here’s an awesome question:

When you’re with someone new, what’s the best way to gauge their adventurousness in the bedroom? How do I suggest new positions, techniques, things considered “kinky” without coming off as someone who has tried everything?  

Well the too-easy answer is:

The best way to gauge their adventurousness or anything is to ask.

“Would you be interested in trying reverse cowgirl?”

“I’ve been fantasizing about tying you to the bed, blindfolding you, and not letting you up until I make you come three times. What’s your opinion of that?”

“How would you feel about possibly spanking my naughty ass until it’s glowing red?”

There’s not a thing in the world wrong with “coming off as someone who has tried everything,” if you are someone who has tried everything.


But of course that’s the *too-easy* answer.

In the real world, there are consequences for coming across as a person who has tried everything – and those consequences may be particularly severe for women. There’s the risk that your new partner will judge you for your experience, right? And while your friends might say, “If they’re going to judge you for your past, they can go fuck themselves,”… actually it would be great if there were ways to talk about these things that maybe minimized the potential for judgment, jealousy, disgust, or shame. Totally.


There are ways, but they’re not foolproof.

And by “foolproof,” I mean “will avoid disturbing even the most foolishly prudish, slut-shaming religious fundamentalist.” There are just some people who insist on being shocked. (Fortunately for us those people are probably terrible in bed anyway, so they’re no loss.)


So here are 5 things you can do to minimize the likelihood that your request for adventurous things will result in good things:

  1. Ask. Ask for permission, opinions, fantasies – do more listening than talking, get a sense of what they’re willing to say and what they’re interested in hearing. 2. Go small. Start with gentle stuff. Break the ice with comparatively benign things. Don’t be like Christian Gray, hero of 50 Shades, busting out the Red Room of whips and shackles on the third date. Self-disclose in bite size doses. It’s like titration in chemistry, or like tempering eggs in baking – you add information little by little, mix it into the conversation until the conversation adjusts comfortably. Then add a little more. 3. Be selective. You don’t necessarily have to disclose that something you might want to try with this new person is something you’ve maybe done with someone else. Certainly not yet. Just as you wouldn’t necessarily talk on a first date about the eight months of therapy you had after your last breakup, you don’t necessarily talk about the kinds of sex you’ve had with other people until you’ve established a certain level of intimacy. 4. Give them a context. Let them get to know other aspects of you. If you feel like a person might be inclined to judge you or feel intimidated by your sexual history, give them a solid context in which to understand that history. Let them about your work life, your education, your family. Put your sex life in the context of the rest of your life, and it will feel more approachable. 5. Confidence and joy. If you present your own history with confidence and joy, you’re teaching your partner how to feel about your history – and even how to feel about their own history! “Here’s what’s true about me,” you tell them with your words. “Here’s how to feel about what’s true about me,” you tell them with your energy, your expression, your kindness.


And finally, remember that the thing your friends would say is true: if someone is going to judge you for your sexual past, your sexual desires, your sexual preferences, they can go fuck themselves.