I Had Quite the Sex Life in My 20s. I’m Wondering If It’s Wrong Not to Tell the Men I Date About It.

How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here. It’s anonymous!

Dear How to Do It,

In my late 20s, I was in a Dom/sub relationship with a much older man. He had complete control over my sexuality and enjoyed sharing me with friends and strangers. I slept with several hundred men in those years. I know some people would find that extreme, but it was fun, consensual, and as safe as possible.

I’m approaching middle age now and have settled down quite a bit. My wild and promiscuous days are behind me. I have no problem staying faithful in a monogamous relationship. My question is, should I disclose my past to any potential new partners? I don’t intentionally hide it, but no one has ever asked me about my sexual history. I think part of it is that men my age don’t concern themselves with things like “body count,” but also, there is nothing about me that would suggest that I’ve had a wild and kinky past. I’m very plain and reserved, I dress conservatively, and if you saw me on the street, you’d probably think I was a librarian cat lady (which isn’t too far from the truth).

I have nothing to hide, but I also wonder if I am unintentionally misleading people by how I present myself these days. I tend to attract sweet guys who see me as wife material. I think I am, but I can’t help but worry that they’d feel differently if they knew the truth. Am I lying by omission by not offering up this information?

—Bad Girl Gone Good

Dear Bad Girl Gone Good,

There’s a delicate yet critical difference between unintentionally misleading people and declining to check whether they’ve made some extremely common assumptions that follow the  Madonna-whore dichotomy.

You shouldn’t have to say, “By the way, over a decade ago, I engaged in and then stopped engaging in these kinky and atypical sexual practices, which left no communicable diseases or other effects that could materially affect you, because my preferences in lifestyle changed” any more than someone else should have to let people know that they played a sport through college or worked as a stock market broker for the first portion of their career. Ideally, we would all be walking around knowing that we cannot assume much of anything about the people we encounter, and specifically asking about things that we would find upsetting in our partner’s histories.

Unfortunately, the vast majority of people will fault you for not informing them of anything that deviates from the norms that they personally feel are safe to assume. They will almost certainly feel lied to if this ever does come up, and a significant amount of society will back that stance because the subject in question is sexual. A small but unfortunate handful of these people, including the ones who are “sweet guys,” will respond to the revelation of a woman’s previous erotic adventures with anger, which can end in violence.

So I’d bring it up. I suggest doing it sometime after you’ve developed enough rapport to feel comfortable having what might be a difficult conversation and are confident that they see you as a whole human, but before any merging of lives, such as cohabitation, meeting parents, or other significant milestones. As with any potentially inflammatory biographical detail, exactly how you can best share this will be based on your personality, the dynamic of the relationship, and the situational context. In your case, I might seize an opportunity presented by a conversation around reminiscing about life phases you’ve both moved on from. Other openings might look like a revelation of one of their own potential dealbreakers, or a discussion of general female sexuality. Keep the tone neutral, stick to facts, and exercise brevity. If the man in question wants details, consider your judgment and boundaries when deciding how much more to delve into.

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Dear How to Do It,

Theoretically, one million people are looking for me: I’m a late-20s, bi woman who wants to have sex with a couple(s). I don’t want to join a relationship, though I would be open to a standing friends with benefits arrangement.

I assume the apps are the way to go here, but I’ve only ever used Tinder, and for casual dates. Where should I be looking? Should I be presenting myself any differently than in a typical dating profile? Is the process much different? Usually, I try to have some level of introductory small talk before bringing a sexual component into things, even if casual sex is the goal. Is that a silly expectation to have when I’m advertising myself specifically as looking for group sex? Similarly, I always have a first date in public, for the sake of safety, comfort, and making sure I actually enjoy being around the person enough to want to take my clothes off. I think this is pretty standard practice, but is there the same expectation of a “date” with a couple? Generally, how can I set myself up for success when stepping into a preexisting dynamic? I want to make sure I discuss what they’re comfortable with before it happens, but in how much detail? Is anything assumed here?

You are correct—an extraordinarily large number of people are looking for someone like you, and there aren’t many folks out there who want to unicorn without significant relationship commitment. This means you have leverage when it comes to setting the terms. Use this power wisely and graciously.

The best dating app profiles are ones where you present yourself truthfully, and clearly and succinctly share what you’re looking for—regardless of whether that’s long-term monogamy or a series of fun romps with an established couple. Feeld does seem to still be the general go-to for seeking out thirds, though Tinder might also be worthwhile. You also never know what counterintuitive shifts in app usage might have taken place in your area, so do pay attention when people mention other places they’ve found threesome partners. The apps are generally a dystopian wasteland at this point, so keep in mind that the extraordinary amount of scammers and bots will mean plenty of folks immediately pass on you because they’re assuming you’re not real, and others will need a certain amount of reassurance.

Many couples who are seeking casual sex arrangements with bisexual women are going to want to meet first, in a public location, for the same reasons you prefer to do so, including safety. Depending on the couple’s preferences around privacy, there may be a need to keep voices low or move to a more discreet setting before discussing details. The same caution may apply to body language that telegraphs flirtation. Absolutely do ask about general boundaries, talk about any specific acts you want or have limits around, and apply the same level of care when negotiating emotional and time expectations. Gauging their experience level can help you get a sense of whether you need to brace for potential emotional explosions. You might also ask about how they like attention to be structured—are you a guest star being focused on, half of a pair focusing on one member of the couple, or one of three humans chaotically and fairly equally giving and receiving pleasure from each other? Plans often change, but it can be helpful to have an idea of how they envision the interaction. As you gain experience, you’ll get an idea of which of these scenarios you prefer.

Look into any local sex clubs that align with your tastes, too. Kinksters are often up for or actively seeking thirds and swingers are as well. Any other hormone-soaked spot that attracts sexually flexible people is a potential venue to meet couples. A major upside is that you’re already in person when you make initial contact. According to Justin Lehmiller’s Tell Me What You Want, which is based on a large survey of over 4,000 people, threesomes are one of the most common sexual fantasies—you may be surprised at how easy it is to organically find folks who are seeking one.

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Dear How to Do It,

I’ve had my eye on a woman, “Amelia,” for some time. The thing is, Amelia loves big dicks, and if I’m being honest, I literally come up short. We’ve been out a few times casually, and she’s indicated that she would like it to be more. My fear is that when it comes time to get in bed, she’s going to be disappointed, and that will be the end of it. Any suggestions?

Rejection might happen, and it might sting, but I suspect it’ll hurt less if the body part in question isn’t dangling in the breeze during this conversation. Is there a time, before you’re both naked, where it would be appropriate to broach the subject?

Start with a simple statement that you’d love to take this further, but are worried that your member won’t measure up. If she’s truly a size queen who absolutely requires a certain length or width, she’ll let you know, and you can judge yourself against concrete dimensions. If she’s open to—or even experienced with—workarounds, she will likely propose those. And if she’s less hung up on the subject than you fear, or so into you that her historical preferences don’t matter, she’ll probably share that. If you’re pretty sure she’s angling for more intimacy, I’d go ahead and get it over with.

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