How to Do It

I Don’t Want to Treat Women Like Other Men Do. This Has Become a Big Problem.

I won’t be one of them.

Man thinking.
Photo illustration by Slate. Photo by Liubomyr Vorona/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,

I am a 31-year-old man, 5 feet 7 inches tall in his socks, who, simply put, hasn’t done it. I lay the fault at my own feet: I’m reserved and prone to self-doubt and overthinking. I don’t put myself out there. Partly, it is that I feel the need to be worthwhile, and the typical delays and debts common to so many of my age don’t help. The larger issue, though, is that I am averse to making moves of my own. I won’t be one of those men with the conqueror’s mindset, who cause so much pain by their actions. I have to know it’s alright to proceed. It has been 10 years since I had a girlfriend, and that relationship was pure luck in the first place, ended by my own habitual lack of initiative.

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It would almost be easier for me if someone else could take charge, and let my doubts and second-guessing be made irrelevant. Better to be told what is wanted, when I already want to please. Not that some such person would fall from above in rural nowhere and rescue me from the fear of dying alone. That sort of daydream is like wishing on a star or waving a magic wand: pointless, and self-defeating. I only have so much youth left to waste. It’s only somewhat about the sex, even, I just crave the connection, just touch alone, to appreciate and be appreciated. I wonder about missed signals. I feel lost. I want to feel flustered, to laugh uncontrollably at some bad jokes, and to feel like my heart is overflowing. How do I even start?

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—Lost at Sea

Dear Lost at Sea,

I’m 36, 169 centimeters tall, and am frequently described as a sex icon. A couple of weeks ago, I sat on my boyfriend’s couch in London and swiped right on about 40 women. After several days (as I was on my way to the airport), I matched with one, and as soon as I told her I’d be back in a couple of months she abruptly unmatched. Without a “No thanks” or “This isn’t what I’m looking for.” I tell you this to illustrate the fact that dating is rejection. I get rejected all the time. It doesn’t crush me, though, because I’ve had about 23 years of practice.

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Think of it like working out. No matter how easy you take it on your first day at the gym, you’re going to hurt the next day. Realistically, probably for the next three days. If you come back consistently, you’ll stop hurting. Then it’s time to push yourself a little harder. You don’t want to go so hard that you strain something (i.e. sink into a depression) but you do want to be living on that edge where growth happens.

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I get the sense that you think you have to be good enough, in terms of a stable income, having hit certain life milestones, and all of that before you’ll find someone interested. Truly, these things do increase your chances of attracting someone. But the biggest factors are flexibility and fate. That relationship 10 years ago, which was pure luck—yeah, that’s how these things work. Make sure you’re tending to your friendships, where you get platonic connection, and reach out for support if the rejection gets to be too much before you find a person you mesh well with.

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It also sounds like you’re a bit submissive, or passive in a way that you’re interpreting as submission. Even in a strong, negotiated BDSM dynamic the submissive has to consent—actively, enthusiastically—for the relationship to be healthy. They have to have their own boundaries and their own desires. So, while you’re putting yourself out there, take the time to think through what you want, need, and don’t want. What makes you feel excited and what makes you feel reluctant? Put that in your dating profile, or be ready to articulate it over coffee if you meet someone you’re interested in. You’d do well to consider the line between assertive and abusive, too. Don’t let your desire to avoid being The Worst of Masculinity make you freeze up forever.

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Dear How to Do It,

I am going through my pre-menopause for the last four years and have lost interest in sex. It’s been a year since my husband and I made out. However, when I mentally prepared myself to cater to his desires and needs and showed him a way that I can help him climax, he wasn’t interested saying he needs me to be equally involved and excited. I tried explaining to him that it’s absolutely OK for him to have the pleasure through me and that I needn’t be excited about it..but he denies this concept. As far as I understand, it’s absolutely fine for one partner to enjoy getting indulged and reach climax through their respective other, even if your spouse isn’t in the mood for it. Am I wrong here?

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—Unclear and Exhausted

Dear Unclear and Exhausted,

You’re both right, and you’re both wrong! What each of you feels is right for you is at odds with the way the other wants to do things, and it doesn’t sound like either of you is seeking to empathize with the other’s position. We know what your husband wants: sex only when you’re excited for it. What do you want? Why do you feel you need to cater to his desires? He’s got hands, an internet connection, a mind to fantasize with, and access to a wide array of toys that work for his anatomy. He can have a whole robust masturbation life, to address any “needs.”

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What makes you feel good in your body right now? It isn’t sex. It isn’t making out. Is it cuddling? Is it baths? Walks? Conversation? Tell your husband what you are excited for—what you do want—and, presuming he’s up for it, do that stuff together. Keep the connection alive, even if it isn’t physical or what we traditionally think of as how married people relate to each other.

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Dear How to Do It,

I (32M) met someone (24F) online about six months ago while she was recovering from a serious car accident and at home all the time. I had just left a six-year marriage and wasn’t interested in dating but liked talking. We started sharing most of our lives, calling each other, and sending each other photos and we got attached. We live in different cities and for a variety of reasons, a real relationship isn’t possible. We agreed on exclusivity while we were talking but knew this is temporary (since we’re both in very messy periods of our lives). She is pessimistic about her odds of a love marriage. I’m also doubtful of my own odds. We decided to meet up a month from now over a long weekend then go our separate ways and stop talking. It was her idea, but I also really want this but am a bit apprehensive; we don’t know what the aftermath will look like.

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We’ve twice tried to stop talking and move on but couldn’t; these attempts were unbearable on both sides. This in part led to us resolving to meet up for better or worse. The most recent attempt was when I knew this had definitely gotten into weird unfamiliar territory for me (very emotional, lots of negative thought patterns, realized I have issues stemming from past relationships). I really have only had casual relationships and just the one marriage that failed in a very boring way and have never navigated anything like this. She initiated and escalated most of this. I mostly was thinking it was harmless and we were staying occupied during mutually difficult circumstances, but also let things get out of hand, too, like going into hypotheticals about how our kids would look. We probably didn’t set appropriate boundaries. I am open to being friends with her afterward, she is not. We debated the merits of immediately casually sleeping with other people to get over each other, or just talking indefinitely until we meet someone else but this would be the same gut-wrenching feelings of being discarded but even worse. How do we resolve this?

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—So Close Yet So Far Away

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Dear So Close Yet So Far,

You both sound like you’re in a soap-operatic film about unrequited love. This is a thing humans tend to do, though some of us do it more than others. We get swept away by the narrative, the obstacles, and the drama. It’s OK but it’s also exhausting—often for us and the people around us.

The “we” you speak of doesn’t resolve this. You don’t separate from each other by resolving things together. You don’t separate by having one romantic long weekend first. You go your separate ways—down your own paths. It is absolutely possible to have friendship and sexual chemistry, or even romance and sex together, and remain friends. But these things are rare when there’s this much emotional intensity. And it doesn’t sound like the two of you are in that place, especially because she says she doesn’t want to be friends with you if what you call “a real relationship” isn’t an option.

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If you really like the drama, by all means, have this meetup. If not, though, focus on you and how you move on from this intense interaction while trusting her to do the same for herself. Casually sleeping with other people might help, yeah, presuming you avoid getting attached in a similar way with another person who is similarly unsuited to you. Look into therapy to see if your pessimism about fulfilling, feasible relationships can shift. Consider what you do want, and write that down so you can refer to it if you’re presented with another situation like this one. Good luck.

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Dear How to Do It,

I’m going to be brutally unpleasantly honest in this letter in a way I never want to be with my partner. She and I (both women) have been together for three years, and it’s the most wonderful relationship I’ve ever had. I feel supported and known and understood, in tons of ways except around sex. We have sex about once a week, which for me ranges from “something I do to show love for my partner, but personally find kinda uncomfortable” to “moderately pleasant.” Unfortunately, we don’t have great sexual compatibility, and I think her sex drive is higher than mine. Meanwhile, my drive for novelty in partners has always been very high while hers has always been low.

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It would be really satisfying and hot for me to have sex with other people, and I think it would be hot to know she’s getting her needs fully met. I’d love to watch, or if not that, at least know that I wasn’t holding her back. A few years ago, I suggested opening the relationship and she said “Maybe in the future” which I took as a no. But now it is the future, and I’m feeling torn by how much I love her and love being together, versus how much I want to have sex I enjoy, particularly sex with other genders. How do I open revisiting this conversation without being manipulative? I do probably need to leave if we don’t open it up, but I don’t want to. And I especially don’t want to frame it in such a coercive way. I’ve had good open relationships in the past, while she’s always done monogamy. I feel so selfish about this but don’t know what to do.

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—Not Quite There

Dear Not Quite There,

“Maybe in the future” might have literally meant “maybe, in the future” which, as you point out, could be now. Start with something like, “Remember when we talked about opening up the relationship? I fantasize about watching you with other people, and having sex with other people myself, and would love to revisit that subject.” The fact that she’s always done monogamy in no way means she’s opposed to opening up.

Do some introspection around why you think what you wrote here is “unpleasantly honest” and where your fears of being manipulative or coercive are coming from. When it comes to avoiding those last two, well, don’t manipulate or coerce her. If you’ve engaged in these behaviors in the past, think back on what you tend to do. Instead of acting that way, be direct. Say what you’re feeling, and what you’re hoping for. If she says no, do let her know very plainly that you love her but can’t continue this way. There’s a difference between expressing your needs and limits and being abusive. Don’t mess with her head, or push her buttons to get what you want if she’s saying she’s not OK opening up. Don’t lie to her or hide the way you’re feeling—like you’re doing now. Be forthright, gentle, and kind.

It sounds like you’re feeling like monogamy isn’t for you. If this relationship doesn’t work out, you can set yourself up for success in the future by dating people who already know they’re into open relationships, or who feel pretty confident that they want to try structures other than monogamy. And have the talks up front, rather than three years in.

—Stoya

More Advice From Slate

I am a dude who has been dating a woman for some time. I think we are set up for failure in the bedroom, and I don’t know how to fix it. The problem, as I see it, is that the woman I am with has a very, very specific sequence of events she likes to have happen for sex. I call this sequence “the Protocol.”

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