How to Do It

My Friend Is Dating Again. She Clearly Never Learned the First Rule of Sleeping With Men.

A man and a woman with an exit sign over them.
Photo illustration by Slate. Photo by nd3000/iStock/Getty Images Plus. 

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,

One of my closest friends (both 40, straight ladies) got divorced two years ago. She slept around a bit after, and frankly, good for her.

The problem is, she’s started looking for relationships with guys, but she sleeps with them on the first date. I’ve been married for a decade so I’m definitely out of the field, but guys … don’t usually take a woman seriously after sleeping with her this early, right? I don’t know how to characterize this without sounding like I’m slut-shaming. I don’t care if she wants to sleep with a meh guy because he’s kinda hot and she’s bored. But when she flirts for weeks with a guy who is close to her kids, and they sleep together on the first date, and he immediately backs off, she’s devastated.

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What can I say here? I feel like a character in a ’90s sitcom telling her the rules say not before the third date!

—Not a Monica

Dear Not Monica,

Sleeping with a guy on the first date is an efficient sorting mechanism to me. Sure, some guys may not respect you afterward, but plenty will, and they’re likely the better partners for your friend if that’s her speed. But if the physical interaction is contributing to her attachment—and it “devastates” her when a new guy backs off after sex—you could suggest that she might want to wait a few dates before she engages in sex to get a better sense of whether the guys want the same things she does first.

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I’m also stuck on the detail where your friend is adding sexual interaction to relationships with people who are “close” to her kids. If this has happened a few times—with people who are significant to her children—I think it’s worth having a conversation with her about looking for dates and potential mates outside of that particular circle.

Otherwise, I’d steer clear of this topic unless she brings it up. If following her dating life gets to be too much, you might also ask your friend for other ways you can support her. It’s OK to set boundaries.

Dear How to Do It, 

I’m a bi woman in my mid-30s and I feel like I’m living a stereotype in a way that makes me really uncomfortable and unhappy, and I’m not sure what to do.

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I was previously in a serious long-term relationship with a man, and while it was great in many ways and I enjoyed our frequent and enthusiastic sex life, I missed having sex and closeness with women. Fast forward to the present, I’m in a serious relationship with a wonderful woman—and I miss sex with men.

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I’ve never been very good at casual sex, and often found it emotionally uncomfortable, so I’m not sure that opening up my current relationship would solve this problem for me. In addition, I know from direct conversation that my girlfriend is uninterested in casual sex with others and feels most secure in a monogamous arrangement, so it would likely not be appealing to her. How do I learn to be satisfied with what I have (which is wonderful) and stop feeling so ashamed of the internalized biphobia I’ve somehow accumulated around this?

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—Why Not Both

Dear Why Not Both,

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A relationship with a second person of a gender different from your primary partner can be significant, committed, and long-term. I think it’s worth asking your partner what monogamy means to her, why that’s her preference, and how strong of a preference she has. It might be the case that she’s open to opening up under certain conditions, and that those conditions are functional for you and the men you might have sex with. Start with getting a better understanding of how she feels, and decide from there whether to broach the subject further.

You’re right that the inability to “pick a gender” is an accusation leveled at bisexual people, and inhabiting the stereotype is pretty uncomfortable. Know that many of us occasionally find ourselves checking off all the caricature boxes, and continue on to live whole lives that go off script. You aren’t setting bisexuality back by matching the cartoon in this moment. Nor are you doomed to embody all of the fears that society has about bisexual people.

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No matter what, being human is uncomfortable sometimes. We long. We yearn. You can purposefully turn your thoughts back to what you do have when you find your longing problematic–—make  a list in your phone, where it can easily add to it, or meditate, or whatever else works to refocus yourself somewhere positive. Take some deep breaths. If you don’t already have friends who are also bisexual, consider trying to make some. And if you want to really dig in, an LGBT-inclusive therapist can be a great ally. Good luck.

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Dear How to Do It, 

I’m a happily married man with a fetish for crossdressing, particularly in women’s lingerie. I’ve been wearing lingerie to sleep since I was 14 (I grew up with three older sisters). I’ve tried bringing it up to my wife subtly, but she doesn’t acknowledge it and thinks I’m weird for bringing up such a strange topic. While our sex life is perfectly fine, it’s just getting to vanilla for me. I really want to incorporate this side of me into our sex life. How do I bring this up to her without causing damage to our wonderful relationship?

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—Worried in Silk and Lace

Dear Silk and Lace,

You don’t say how old you are, but I imagine you knew you liked wearing lingerie to sleep long before you married your wife. This would be easier if you’d told her directly about your kink before you got married, but you didn’t, and here we are. It’s likely that she’s going to be some amount of upset with you for withholding this information. Damage happens in relationships, and frequently so do repair and resilience. I can’t promise you’ll bounce back from this, but this probably isn’t a cheating-level issue.

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It might be that your wife’s reaction is less because she thinks you’re “weird” and more that she’s confused about why you’d bring something like that up in the abstract. Pick your tim—when you’re both comfortable, have your basic needs taken care of, and have time and privacy—and be direct. If “I’ve been dropping hints about crossdressing because it’s my biggest turn-on and I haven’t known how to tell you” works, great! Maybe it’s “I find comfort in wearing women’s lingerie, and I’m worried you won’t accept that about me,” or some other phasing. Figure out what you want to say beforehand and keep it as concise as possible. Be prepared with an apology, and also with an example of how this can include her if that’s something she’s curious about. Be prepared for other outcomes as well—presumably you know your wife and can make some predictions about how she’s likely to react, and how best to frame this to her. Good luck!

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Dear How to Do It, 

I’m a mostly straight, fairly tall, fat woman of color. I’m pretty self-confident and love myself to the best of my ability, which sometimes requires being body-neutral instead of body positive. I love sex and generally don’t have hang-ups about my body in bed. But I really, really struggle with dating. I want a partner, but the few times I’ve met someone whom I think I might be able to commit to and have a life with, they’ve turned out to be dishonest in one way or another. I also like casual sex, and when I feel like I need a pause on more “serious” dating, I seek out more casual relationships because again, I love sex and would prefer not to go without.

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For the last few years, I’ve mostly connected with men in open or poly relationships in my casual dating phases, and I have no issues sleeping with someone who’s in an ethically non-monogamous relationship, except for one thing: I live in a huge, diverse city, and every ethically non-monogamous man I’ve connected with, regardless of his own race, has a petite, white female partner.

I already feel pretty devalued by general society when it comes to dating, and literally devalued by dating app algorithms, and somehow, this feels worse—that these men are eager to sleep with me and willing to be open about those feelings, just because they’ve already found a thin, white, conventionally attractive partner. I feel like so many non-monogamous folks in their dating profiles (and on our dates) talk about how liberating and progressive their relationship structures are, but I can’t help feeling like there is something secretly toxic underneath it all in current poly culture. Not because I think everyone is lying to themselves but because (at least the folks I’ve interacted with) aren’t particularly introspective about this aspect of their lives. Honestly, if I do ever find my own long-term partner, I think I’d want to consider opening up my relationship once I’d really felt secure in it. But right now that feels like it’s never going to happen. How do I come to terms with this? Or address what I see in the culture with the folks I date/sleep with?

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—Poly Problems

Dear Poly Problems,

Taking breaks from searching for a significant partner when you need to is a great way of taking care of yourself. Well done. And since you enjoy casual sex, it’s wonderful that you’re engaging in hook-ups when you find appropriate partners, too. Ethical non-monogamy has issues, like other frameworks for sexuality or even general human interaction, and you’re on the brunt-bearing end.

I asked Dirty Lola, a sex educator who has extensive experience in poly communities, for her thoughts here. She said your feelings are “honestly right on the money,” and she said she too had seen “so much toxicity” in the ethnically nonmonogamous/polyamorous community, much of it centered on racism and fatphobia. She continued:

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There are so many people out there pushing this narrative that ENM and Polyam are for the thin, white, beautiful, and able-bodied. Not so much in what they say but by what they do, what their slice of the community looks like, and who they keep out. It’s a mess. I’m honestly not surprised to hear your story. It’s very close to my own and I learned early on that if I were to have any peace in my slutitude, I would have to talk about these things. Even if it means cock-blocking myself. I’m not saying every polyamorous man with a thin white partner who is attracted to you is out to appease some kind of fetish. I’m saying a bunch of them are, and you have to weed them out early so you don’t have to deal with an onslaught of toxic behavior.

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Lola shared her own way of dealing with this:

I like to let folks know where I stand early on. I’ve been known to ask potential suitors if they’ve ever dated a Black woman or a woman of color. When I’m feeling less bold, I’ll ask what drew them to me seeing that I’m so different from their partner. I’ve also gotten really good at combing their profiles for red flags (people tell on themselves all the time with those questions). I weigh their answers accordingly, and those who are actually genuine in their attraction tend to be up for the hard conversation.

This can all be a bit daunting so I will also offer you this: only go to these lengths if it feels worth it. You don’t have to solve all that is wrong with the ENM / Polyamorous community on your own. You deserve to get your clit wet and keep it moving if you so wish. So when it’s worth the pleasure but not the trouble, take your pleasure and let someone else handle the trouble.”

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It’s not your responsibility to help everyone you meet to interrogate their own biases and bigotry. Expend that energy at your own discretion.

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As for coming to terms with the dishonest people you’ve encountered as you seek a more serious partner, it may help to remind yourself that that isn’t about you. Keep taking breaks when you need to, nurture your non-sexual relationships, and do all your self-care things. It isn’t right, but you’ll get through it.

More How to Do It

I am an older woman who has recently gotten back into the dating game. My problem is I hope going to be fun for you. Ha ha. So I am a semi-conservative woman and am hoping to meet someone similar. But I also am very sexual. I have only been intimate with one man since dating, and I was thinking he could be the one. But when we decided to play, there was a … problem I’d like to address beforehand next time.

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