How to Do It

All My Failed Dates Have Exactly Two Things in Common

I’ve had a bumpy dating road.

Man scratching his head with multiple Xs above him.
Photo illustration by Slate. Photo by  feedough/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’m a part-time sex worker in my late 30s and have been in some part of the adult industry since I was 18. I have a “straight” job but it doesn’t pay very well. I use sex work to supplement my income. I’m also hoping to find a long-term, monogamous relationship. After having someone threaten to out me if I didn’t continue dating them, I like to wait until giving someone that information. Being outed would cost me my job, my relationship with my parents, and possibly my home. I’m also willing to stop if it’s a dealbreaker for someone. I’d rather have a satisfying partnership than the extra income.

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I’ve had a bumpy dating road for the last 10 years. They all had two things in common. The first is that none cared about me being a sex worker. They were all kind and easygoing about it and understood why I waited to disclose it. The second is that they were all pretty ambivalent about our connection.

A few months ago I met someone really special. Smart, kind, cute, fun, thoughtful: the whole package. And by some miracle, he enthusiastically liked me back. We hadn’t discussed if we were dating other people and weren’t exclusive but I was hoping we’d get there. I came out to him after we’d been dating for about six weeks. As part of that conversation, I explained why I waited. He said it was OK in the moment. He texted me for about a week as if everything was fine, then started talking about needing to process what I shared and started to slowly fade. He never really said what he was struggling with specifically although it seemed like he was bothered that I told him at all; like it was too intimate. He wouldn’t speak to me in person about it and after a few weeks he broke it off.

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It’s embarrassing because it was only two months, but it hurt. A mutual friend told me today that the issue was not telling him when we met. He feels betrayed and misled. I can understand why someone would feel that way, but I’m also nervous about the potential harm of being out to someone after only a few dates. If I’m lucky enough to meet another person who actually likes me back, do I need to disclose it right away? Are only ambivalent people going to be OK with me waiting? I don’t want to go through this again.

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—Crying in the Closet

Dear Crying,

You list some very real reasons to stay in the closet: fear of ostracization by family, loss of your straight-world career, and the possibility of being unhoused. Most of us—us being current and former sex workers—don’t get to transition into careers where our experience in sexuality is an asset. And, despite public outcry during the August 2021 OnlyFans porn ban that “sex work is real work,” we remain subject to stigma from our loved ones, banking and payment infrastructure, landlords, and other crucial entities. As I watch public opinion become more accepting, I’m aware that the systems that control our ability to survive aren’t budging yet, and brace for the pendulum to swing back. Without policy changes protecting us, we’re in a precarious position.

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The whole package, as you put it, needs to include a willingness to learn about and empathize with these realities. It needs to include acceptance of who you are right now and the life you’ve lived that has made you who you are today.

I get the sense that you may be approaching dating from a scarcity mindset. This is a common experience, whether we’re talking about sex workers, disabled people, people of color, neurodiverse people, people with criminal convictions, trans and non-binary people, kinksters, divorced people, fat people, older people—really, anyone who hears repeated messages from society that we’re somehow less than. If there’s room in your budget, a sex work affirming therapist can help you sort through the shame you’ve likely internalized. If not, a little bit of mindfulness can help you turn your thoughts toward something more self-accepting when you begin to question your value. And some time spent thinking about your awesome qualities—times when you really shine, what you’re particularly great at, and what you love about yourself—can be a useful antidote.

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You have to weigh for yourself the risks of being outed, or coerced with the possibility of outing, against the risks of being disappointed again when someone you like turns out to be missing that quality of understanding. It’s your choice. I can’t make it for you. And, I’ve got some bad news; dating, whether you’re a sex worker or not, is a gauntlet of wacky experiences and hurt. There’s no way around that. The world absolutely holds humans who will be a wonderful match for you, but nothing can guarantee that it’ll be an easy or quick process. Take breaks when you’re feeling fried, and take care of yourself every day. Good luck.

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Dear How to Do It,

Do you know of a method for donating/recycling sex toys? I feel like some things, like cheap metal handcuffs with no sexy time vibes, can be passed off as part of a Halloween costume and given to my local donation center. But what do I do with things like the nylon under-mattress restraints or perfectly functional silicone dildo I no longer use? I feel terrible throwing them away and adding to the landfill, but I can’t just donate them or put them on Facebook Marketplace either. What’s an eco-conscious gal to do?

—Our Sex Lives Are Killing the Planet

Dear Killing the Planet,

I applaud your desire to be environmentally conscious. There isn’t an easy solution, though. If sex toys are recyclable at all, they require special handling. This Mashable article from earlier this year dove into this whole mess, stating, “Sex toys are rare enough, and so diverse in form, that they’re not really on most recyclers’ radars, and thus aren’t accounted for in many automation systems. So, during sorting, toys or their deconstructed parts may still get diverted into a trash pile instead of processed for recycling.”

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If you’re in Canada, Come As You Are accepts silicone and ABS plastic toys for recycling. And you can seek out a center for recycling electronics or any toys with electronic or electric components in whatever country you’re in. One thing to consider, though, is the carbon footprint of getting these toys to the place where recycling may be able to happen. So, you’ll want to make sure that the items you’re sending can be processed there. It’s worth calling or emailing ahead.

If you have friends who are sexually exploratory, nylon under the bed restraints seem pretty easy to sanitize and pass on. Moving forward, you can be more selective and do more research before purchasing. And it might be worth hanging on to that dildo for a while in case it becomes appealing again in the future.

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Dear How to Do It,

I’m a cis 23-year-old woman. There’s this guy on campus, “Brad.” Brad is smart, funny, good-looking, and by far the best hookup partner I’ve ever had. The problem is that he knows it, and he’s all smug superiority and seems to half view sex as showing off how good he is at pushing my buttons. Every time I get out of bed with him, I feel slimy, but the sex is good enough that I keep coming back.

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I kind of want to stop seeing him, but I also want to lock the bedroom door with him and not come out for a week. Should I just walk away? Or is there a way to make the experience less confusing in the future?
—Mixed Up

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Dear Mixed Up,

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When you say Brad pushes your buttons, I’m wondering whether this is in the context of knowing all your spots and how to stimulate them, or something more like manipulation. If it’s the former, you can absolutely ask him about his bravado—is it a bit of a show because he’s heard that confidence is sexy? It might be possible to have a dialogue that helps you understand his behavior better, and it also might be possible to request that he turn the dial down when he’s with you.

If the latter is the case, you might have one firm conversation where you communicate to him that you don’t enjoy these aspects of the experience and that while you do very much like having sex with him, you’re getting near your limit. Be prepared to tell him where your boundaries are, and give specific examples of what is unpleasant for you. Listen to how he responds. If he’s open to your feedback, great! Give him a chance to change the way he relates to you. If he invalidates your experience, minimizes the aspects you point out as problems for you, or refuses to engage, there’s your answer—time to walk away.

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Dear How to Do It,

My husband and I were both very young (21 and 22!) and both virgins on our wedding night, as we came from very religious backgrounds. We’ve been married for 18 years now, and while I love him, I find myself extremely disappointed and frustrated with our sex life. He is extremely shy and awkward when it comes to sex—STILL!—and absolutely refuses to initiate sex with me EVER, despite me repeatedly telling him how much I need that from him. He just keeps telling me he “feels weird” being the one to initiate, and he’s not willing to change just because I “need to feel needed.”

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When we do have sex, he is awful at foreplay (i.e. he thinks honking my boobs a few times is sufficient), and he refuses to touch or go near my genitals with anything other than his penis (he has sensory issues and doesn’t like the feel of my wetness on his fingers). So, if I ever want to have an orgasm, it’s 100 percent up to me. At this point, it’s easier to just masturbate, since I have to take care of everything myself anyway. At the beginning of our marriage, I hoped that he would improve with time and experience, but this obviously hasn’t been the case. I’ve tried telling him, showing him, describing to him what I need, watching porn with him, incorporating toys—everything embarrasses him and he just shuts down and refuses to try anything new.

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I love my husband, and I don’t want to leave the marriage—everything except the sex is great! I find myself fantasizing more and more about having an affair. I so desperately want some passion in my life! Is it ever justified to cheat on your spouse when it seems impossible for your needs to ever be met? Do I have an affair? Keep waiting and trying to change him? Resign myself to a life of disappointing sex and a passionless marriage?

—Forever Newlyweds?

Dear Newlyweds,

You and your husband come from a culture that pushes people toward marriage before they’ve had a chance to see if they’re a sexual match. Start with compassion for yourself, and also for his position. Lutheran pastor Nadia Bolz-Weber describes, in her book Shameless: A Sexual Reformation, Christian couples who struggle, once they’re married, to engage with each other sexually because of beliefs about sex being bad, dirty, and, well, shameful. Is it possible that the reason your husband is so shy, awkward, embarrassed, and likely to shut down is that he’s flooded with these negative feelings about sex? You don’t say which tradition the two of you were raised in, but regardless of specific spirituality, Bolz-Weber’s book might provide some useful insight.

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You’ve certainly tried telling your husband what you need, but I’m wondering how many conversations you’ve had about what’s happening on his end. Have you talked about how he feels about sex? Have you asked him for more detail about what he means when he says he “feels weird” initiating sexual interactions? Have you had conversations about your views on the religion you were raised in, its beliefs on sexuality, and the effects those beliefs have had on the two of you? If you have, and those conversations have been fruitless, counseling could help you two have these discussions. If you’re still in that religious community, your religious leader might be a place to start. If you aren’t, a couples therapist who is currently outside that faith themselves would be ideal. Finding this person is a tall order, I know. AASECT’s provider referral directory can help direct you to some names, and from there you can reach out to providers to ask about their comfort level around taking on clients from your particular religious background.

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If you’ve tried all of that, or you do try and none of it helps, you’ve got a big choice to make. You have to weigh for yourself the benefits this marriage brings you—be cautious of overvaluing the security of the known—and the benefits that a partner who has a similar view of sex would bring. If you decide to leave, know that finding that partner isn’t guaranteed. And if you decide to stay, look for passion elsewhere—not in the arms of an illicit lover, but in other aspects of life. Feel free to fantasize about taking other lovers, if that provides an emotional or sexual outlet, but don’t put those thoughts into action. There’s a third option, which might be so intolerable to your husband that it destroys your marriage anyway: opening up your marriage. Consider the potential fallout and carefully weigh your risks and rewards. Good luck.

—Stoya

More Advice From Slate

About a year ago, I confronted my husband of more than 10 years with evidence that he had surreptitiously set up a web camera in our bedroom, with the intent of watching me masturbate while I was home and he was elsewhere. He admitted it, and it has been an extremely difficult year working through the anger, betrayal, and feelings of violation.

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