Sex advice: I was fine to give the guy I was hooking up with an assist the first few times. But three strikes and you’re out.

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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 woman, and I’ve hooked up with this guy three times now. I get along with him well as a person, and the making out and foreplay are always fun. He’s been easily available for a quick “you up?” text, which is honestly not the easiest thing to find. So on that side, things are good! But he has trouble with erections.

The first two times, I was fine with fooling around and ended up giving him a blow job, which inexplicably got him hard when penetration didn’t. This third time, the same thing happened, and I think I might’ve rolled my eyes or otherwise expressed some frustration at him going soft when we attempted penetration and him then expecting me to give him oral. It was a bit awkward, as he seemed taken aback and a little hurt that I expressed annoyance, but I ended up giving him oral anyway. The problem is he’s never reciprocated or otherwise gotten me off! He’s done a bit of fingering before we attempt penetration and then never offers to reciprocate once I’ve gotten him off. Is it worth a conversation about this, or cut my losses?

—Never My Turn

Dear Never My Turn,

While it’s certainly possible that a conversation about reciprocation (or about wanting to prioritize all the sex that’s possible without an erection present, or both) will result in an apology and a permanent change in this guy’s sexual behavior, it’s more likely that he’ll ask for support working through some kind of sexual anxiety or his response will reveal that he doesn’t think your pleasure or enjoyment is important. When you open the topic, you are creating the potential for the whole range of possibilities. I do want to underline the fact that many straight men actually are walking around with such poor sexual education that it is real news to them that a woman might experience pleasure, and sometimes that information causes a major reframing of what sex is and can encourage them to learn how to show up as enjoyable lovers.

For me, a clear confirmation that the person in question is selfish about sex would absolutely make a conversation worth it. And, depending on how much I liked the person and how much extra energy I anticipated having over the next several months, doing what I could to help them get past whatever angst was interfering with giving sexual pleasure and keeping an erection could be both feasible and fulfilling. If you want to have relationships that are more long-term and substantial than a hookup, you’ll likely need to provide or receive that kind of erotic safe space at some point. Whether this guy is someone you eventually have that type of relationship with or not, if that patience and understanding are what he needs and you want to try to provide it, that experience is likely to serve you well in the future.

That said, I don’t know how much you actually connect with him as a person, what you have your own anxieties around, how much bandwidth you have to spare, or whether you would find the same value that I would in any of these scenarios. For some people, being hit with blatant misogyny in the face of a request for a little fingering isn’t worth the risk. For others, a casual sexual partner opening up about emotions is a nightmare they feel both unqualified for and kind of revolted by. You tell me: Are the potential upsides worth the initial hassle of starting the discussion, and the potential risks?

Regardless, know that you owe a person you’ve hooked up with three times precisely nothing other than basic human decency, so you have no obligation to sit through any unpleasant exposition of why he sees your pleasure as something that can be neglected, no responsibility to provide any significant emotional support (and especially none to agree to any particular request or expressed need), and, really, nothing is required of you other than a polite, “This isn’t going to work for me” if you decide to opt out, whether that’s now or during a conversation.

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Dear How to Do It, 

I need advice about reentering the dating world with a health issue. I, a 54-year-old straight man living in a large city, ended a 16-year marriage right before the pandemic. I lost all momentum for meeting new people, and haven’t been intimate with anyone since my marriage. On top of that, I have an invisible disability (chronic migraines) that leaves me drained of energy and extremely sensitive to noise, smells, and lights (goodbye to most restaurants and bars). My lack of energy and “presence” contributed to the divorce: Migraines and medication often leave me feeling emotionally blank for days.

While I’m not opposed to a committed relationship, I feel it would be fairer to others (and myself) to be upfront about seeking a casual but ideally ongoing arrangement right now. I’m not looking for a caretaker or to jump back into marriage or cohabitation. I don’t want to disappoint someone else who might be angry when I’m emotionally unavailable due to illness (my marriage gave me some stubborn fears about that). I’m physically lonely and craving some intimate human connection in a world where public cruelty is becoming the default. I may not always be an overt emotional dynamo, but I do have kindness and passion to share.

When I think about setting up dating profiles, though, I start spinning out regarding how to present myself. I don’t want to come across as some cringy, middle-aged divorce guy belatedly sowing his oats. But I’m torn about revealing too much concerning my circumstances upfront. And given my sensory issues, I don’t want to make a woman feel unsafe by being challenging about the types of public spaces we could meet up in. (Red flag, anyone?) Should I just be completely open and let people screen themselves out? Having been out of the dating pool since the early aughts, I’m approaching this as an amateur, and I’m not even sure which apps might be best for me, especially in my 50s. And I think I need to start researching the quietest, darkest coffee shops and bars in my city.

I had a thought that it could be interesting to try meeting women already in partnered, but open relationships. I’m not poly at all, and monogamous when committed, but something casual is OK. That way, there’s a pre-existing framework and understanding that could mesh with my circumstances. But is there even an app that could facilitate that? Perhaps Feeld? Or alternatively, are there any decent apps for people with disabilities/health issues that actually have a viable number of users? I checked a couple out pre-pandemic, and even in a major city they were deserted. Ironically, one of the only silver linings of my invisible disability is that aside from some gray hairs, spending a good chunk of the last 15 years like a vampire in a darkened bedroom has dramatically prevented aging and wrinkles on my face, which may help when joining photo-based dating apps. Though this is not a skin-care regimen I recommend to anyone. Sunscreen is much easier! So, any advice on my best path forward?

—Willing But Alternatively Able

Dear Willing But Alternatively Able,

I get the sense that you tend toward analysis and systematic thinking. If you haven’t already, apply some of that energy toward understanding what tends to set off a migraine and speed up recovery, and how long recovery tends to take. While it would be absolutely lovely if this effort could reduce or even solve your problem, the reason I want you to gather this information is so that you can communicate as well as possible about what exactly you need and what will likely cause a last-minute cancellation on your end.

The latter sets you up to be able to say things like “barometric pressure changes trip me up, and rain is forecasted for next week, so I’d love to commit but there’s a 65 percent chance that I’ll need to postpone fairly shortly before the date,” at which point they have the opportunity to agree or wait for a time where you’re less likely to have to cancel. The former allows you to precisely choose the options you’re offering for meeting places, and explain what sorts of places are likely to be OK for you if they want to suggest somewhere themselves. Weather permitting, spaces with gardens or streetside seating are often easier from a sensory standpoint, though they come with closer exposure to the sounds of car engines, horns, and sirens. You might also want to get creative about meeting spots. If you’re genuinely into books, pottery, or other hobbies that can involve quieter public spaces, those are great options—especially as people have become less interested in bars due to health reasons or the sheer expense. Think about where you hang out with your friends, and what works for you about those places.

Similarly, being able to define what you mean by “casual but ongoing” will help you describe what you’re looking for. Introducing our desires in terms of what we don’t want, often creates an air of negativity or uncertainty that can be more off-putting than any particular personal complication. I also worry, based on the ways that your own concerns are so tied to how your migraines affected your former marriage and your statement that you want intimate human connection, that you’re still carrying a lot of pain from your divorce and may, on some level, be hoping that a casual relationship will soothe some of that pain. Every once in a while, someone does quickly find a partner who wants the same type of relationship they want and who sees and accepts them. Far more common, though, is a long string of mismatches, rejections, and usually some amount of that cruelty you’re hoping to get a respite from at one or more points along the way. This can wear heavily on people who have a solid base of emotional resilience and a stable friend group. It crushes people who are hoping to find emotional healing in the arms (or lap) of someone they just met on an app. If “intimate human connection” is a euphemism for getting laid, though, by all means disregard my concerns.

I’m not sure where your understanding of polyamory comes from, but what you describe is different from what I’ve seen of that style of relationship structure. If you have friends who practice polyamory, asking them where to meet people in your area (which apps, whether there are social events) and double-checking whether your expectations are reasonable in your community would be your best move. If your ideas of polyamory are based on a fairly superficial understanding, know that in my experience, people who do polyamory tend to expect the “amory” part in a mutual manner. They are wary of potential partners who have no experience in that world. Think through what it is about commitment that means you require monogamy, and what defines commitment for you. Consider how you’ll handle the situation if you develop feelings, or the two of you develop habits that change your feelings toward an open arrangement—not how you’d like to handle the situation, but how you actually will.

The sorts of people you’ll find on each app vary with time and location. Feeld might be the place for you, or you might find that in your area, the users are all looking for largely vanilla, completely monogamous, long-term relationships (based on what people have told me in the past couple of years, this has been the case in more than one U.S. city, and wow is it a shock to me). Whether or not you’ll find an appropriate partner for the kind of relationship you’re seeking in any given group is also not guaranteed. Dating is a process. Finding someone who fits in your life, and whose life you fit in, often takes time and persistence. The good news is that women who are remotely in your age range will probably have some physical complications of their own to navigate, even if they don’t have a disability (or do, but wouldn’t identify as such), so the lack of high traffic apps for that specific group is unlikely to prevent you from meeting potential partners who have direct empathy for the realities of having a body.

Whether you’re fishing in disability-specific pools, the sea of swiping-based dating apps, or meeting people in person during activities that are meaningful to you, there will be difficult emotions. Someone is probably going to get angry at some point. Someone is probably going to want more from you than you can give. And you’ll probably want more from someone else than they can or will offer you. Ask yourself whether you’re prepared for that, and know which friends you can lean on when an evening really hurts. If the answers are “not sure” and “no one,” start with therapy.

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Dear How to Do It,

My husband and I (I’m a woman) have been together for over 10 years and are in our mid-30s. We have busy jobs and a toddler, but still manage to have sex a few times a week. I orgasm at least once, generally speaking, usually two to three times, and he always finishes, but I have been worried for a while now that I might not be active enough in his pleasure. We don’t really do oral, and outside of some brief foreplay with manual stimulation, I don’t really do much else that is specifically for him. He only “lets” me on top sometimes, but only after I’ve had a decent orgasm. I find that I want to do more, but I am not sure how to change up the dynamic, or honestly, what I should even do.

—Pillow Princess

Dear Pillow Princess,

Where is your worry coming from? You don’t mention your husband voicing any complaints, and you describe him as allowing you on top only under certain conditions. I can think of several reasons, from the examples of sex in mainstream movies and television to preferences for certain dynamics, that your husband might feel more comfortable driving the action and being on top. He also might be concerned about your pleasure and making sure he’s doing enough for you in a way that is similar to your own feelings. There’s a chance that he’s worried about injury to his penis (which is a thing that can happen, has the potential to be a serious medical emergency, and therefore can be quite a fear).

If there was anything specific (a position, scenario, technique) that you had a desire to bring into your sexual interactions, I’d say go for it—gently, while paying attention to consent and the potential withdrawal of it, of course. But you don’t have a particular idea or wish to fulfill, other than to alleviate a concern that you aren’t an active enough participant. Have a talk with your husband and find out if he would even want anything else in bed. It could very well be the case that both of you are stressing about whether the other is satisfied, and the only change to the status quo that would be beneficial is open discussion of how you’re each otherwise happy with how things currently stand.

My Mom Is Helping a Local Laid-Off Librarian Out of the Kindness of Her Heart. But It’s Going to Cost Me.

If your husband does want you to take charge more, or you develop an urge for something outside your standard set of moves, you can tackle the hows of that particular practice then. In the meantime, know that there are far more people having warm, connected, and otherwise simple sex than you’d think. In film and TV, the sex scenes have to have enough drama to justify screen time. In non-fiction discussions, like this column, the data is skewed by the fact that satisfied people don’t need advice, and there’s not much to write in response to “my spouse and I have a wonderful, connected relationship and figured out what works best for us sexually many decades ago” other than “bravo and please feel free to include any tips you’ve learned.” One book, Peggy Kleinplatz and A. Ménard’s Magnificent Sex, explores what’s working in those types of relationships. Reading those stories may go further to assuage your worry than any list of ideas for spicing things up for the sake of spice ever could.

—Jessica

More Advice From Slate

I was in a long-term relationship (after getting a divorce) where the sex was absolutely mind-blowing. I had never had sex this good. Ever. But the person I was having this great sex with just wasn’t into more than that. The sex kept me in the relationship way longer than I should have stayed. It was a bad break up, but I had had enough—despite the mind-blowing sex. Enter the new man that treats me like an absolute queen. No one has ever treated me this well, either. He’s an absolute keeper. My friends love him, my employees love him. He’s amazing. However, the sex is atrocious.

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