Updated: August 19, 2022
How to Do It is Slate’s sex advice column. Send your questions for Stoya and Rich to email@example.com. Nothing’s too small (or big).
Dear How to Do It,
I’m a mid-40s hetero man with—well, I’m not sure I’d go so far as to call it a fetish, more of a hankering. I’m attracted to older ladies. Older as in 60s, 70s, and sometimes beyond. I’m not especially looking for an older girlfriend, more along the lines of fun and friendly banging and general foolin’ around. From what I’ve found, the usual online suspect sites (rhymes with Cinder) aren’t great places for finding willing ladies of a certain age. I am a registered nurse, and I work in a hospital, but that isn’t, ahem, a particularly good or ethical place to play pick up. I happen to live in a rural-ish area that is demographically skewed toward an older population, and I know for a fact that people tend to be horny creatures regardless of age. Any suggestions on how I can go about hooking up with the Golden Girl (or Girls) of my dreams?
Dear Golden Guy,
Surely you have the capability to dig up dating apps and sites specifically tailored for so-called “cougars” and the people who love them? Your tastes lean older than typical for those sites, but it’s worth a shot. Other than that, go to where old people go. Try bingo. Or the library. A Denny’s at 4:30 p.m. Are there social clubs near you? A VFW, say? I wouldn’t recommend a senior center, because I don’t think you should be interloping but instead placing yourself in situations where you may meet someone who matches your taste. This will require laser-focused engagement on your part. It’s not going to be as easy as, say, if you were a queer man in a major metropolitan area so teeming with options that a wind tunnel could whisk willing men into your lap. Some of us have tougher burdens of desire than others. Them’s the breaks.
I would be remiss if I didn’t at least comment on you mentioning your job as a nurse, which presumably puts you in close proximity of the demographic you crave. Wait around long enough and people will tell on themselves; it took you half a dozen sentences to do so. Your question would have been just as answerable without that information and my paranoid tendencies make me wonder if you included it as a fake out: “I’m not a creep! Look at me not creeping on these older women that I might otherwise be inclined to creep on! I’m telling you all of this precisely to show how not-creepy I am!” I don’t know, that’s slightly chafing my balls. Who knows what Jedi mind tricks you’re capable of? (And if that is what you’re doing, stay away from Yoda.) Anyway, I just want to, I guess, affirm you here by advising you to keep living by the idea that your hospital workplace isn’t a good or ethical place to pick up elderly sex partners, because you’re absolutely right. It damn sure isn’t.
Dear How to Do It,
I’m a 30-year-old man. During my life I’ve been occasionally attracted to men, but was more attracted to women, so to keep it simple, I’ve only dated women. I’ve now been in a serious relationship with a woman for three years, it’s going great, and recently I told her that I have sometimes been attracted to men, and she said that if I wanted to explore this, she was fine with it.
I’ve become very intrigued with the idea, I’m just not sure how to proceed. I’m not totally sure what I’m looking for. At the moment, to start, I want to make out with a guy, and see where it goes from there, maybe more, maybe not. I’m not looking for another relationship, just a few flings. Is an app the right idea? I’m not sure about Tinder; I don’t want someone to think I’m looking for a relationship. And from what I’ve heard about Grindr, that doesn’t seem like the right idea, because guys would probably be expecting more than what I’m necessarily looking for (to start out at least). Is a gay bar the right idea? I live in Brooklyn, so there are options out there. I’d love to hear any advice on the best way to find partners who are interested in this specific situation.
—Just a Kiss
Dear Just a Kiss,
I love that you’re ripening. You’re on the cusp of a new (yet familiar) kind of fun. You’re probably right about Tinder, though plenty of guys have used it for the same kind of casual encounters that other apps have a stronger reputation for facilitating. I disagree that the tried-and-true hook-up apps (Grindr, Scruff, et al.) are necessarily a bad idea, though. Firstly, labeling yourself as straight/curious on an app for men who have sex with men will likely get you a lot of interest, and more options mean the greater ability to find someone who will be into what you’re into. You can explain yourself, and most guys will pay attention. For better or worse, this sort of sexual threshold crossing remains fetishized among queer men (let’s save a political interrogation of this for another day), and I’m sure there are more than a few who would be open to exploring with you at your pace. If you were to go this route, you’d find that this particular arena tends to foster explicit conversations about exactly what people are looking to do, so it won’t be strange for you to be explaining yourself in depth. You will almost certainly receive messages from guys who want to be pounded out (for example) and immediately lose interest when they realize you are not a dom dick distributor at the moment. The process may be frustrating at first, but I think a hook-up app is at least worth a gander.
And yeah, try a bar. I think it’s always better to meet someone in person because of what apps cannot convey, much like restaurant food usually tastes better than takeout. You just get a much better sense of chemistry, of a guy’s smell and swagger, in a face-to-face scenario. I encourage you to be upfront with your inexperience and desire for a snail’s pace. Hold onto that and, to the best of your ability, resist pressure to exit your comfort zone. Keep this experience positive. You’re opening yourself up to the world of expressing and receiving affection from men, and that can be such a beautiful gift when cultivated with communication and care. I’m excited for you.
Dear How to Do It,
I am a 30-year-old woman who’s been married for just shy of eight years to a great guy the same age I am. We don’t have any children yet, but I am in my early second trimester with our first. When we first got together, as seems to be the norm, we had a great sex life. GREAT. I can’t emphasize that enough. Both of us had plenty of experience before each other, but he is only the second partner that I’ve experienced an orgasm with. I know for it to happen, I have to feel deeply bonded and connected with the person. Sometimes it happens, sometimes it doesn’t, but I’m OK with either scenario because I enjoy the emotional bonding that goes on during sex for us.
The problem is that during our relationship, his interest in sex has come pretty close to flatlining. I’d say it started slowing way down about a year and a half into our marriage. We continued to have great sex, it was just far less often than the once or twice a week when we were newlyweds. I realize everybody goes through a honeymoon phase in relationships, and sex naturally becomes less frequent than in the early stages of relationship. After our third anniversary, we were having sex maybe once a month. Then it was once every six weeks, then every couple of months.
He has always been aware that I have a high libido, and this has frankly created a fair amount of resentment and frustration on my part. We’ve had endless discussions about it, both at the moment and also in a neutral environment when we aren’t in a fight. I’ve explained, tried reasoning, and even just accepting that he just doesn’t want to sleep with me as often as I want to sleep with him. But it’s done a number on my self-confidence, to say nothing about creating feelings of uncertainty in regard to how he really feels about me. For his part, he insists that he’s still attracted to me, and that he does in fact still want to sleep with me. I have never turned him down even when I was absolutely exhausted or not feeling well. But because he started to reject my advances and tell me he was too tired, and would get angry if I brought up that he would almost always decline my advances, I stopped attempting to initiate. That hurt me quite a bit, and I’ve told him so in no uncertain terms numerous times over the last five years. He would apologize, but the same pattern would continue anyway. He always says he’s sorry when I tell him the damage it’s doing to the bond in our marriage. I have approached this from every angle to try to help him see that it’s hurting me.
I realize he probably has a lower libido than I do, and I’m OK with that, I promise. I just want there to be some kind of mutual compromise because I am so lonely. I’ve tried to let go of the hurt and resentment it’s caused. But nothing changes. This is especially difficult because I’m dealing with my body changing and having to get used to it becoming a house for the next six and a half months for another person. I have explained calmly and rationally the effect it has on me emotionally, along with how going through physical changes when he still doesn’t show any interest in sex is affecting me. He always promises to change, but never does. I really am at a loss here because he’s had his testosterone levels checked more than once, he’s in good physical health, and nothing has happened in our marriage precipitating the drop-off and what feels like subsequent emotional abandonment. He stopped attempting to connect with me or show any physical affection apart from the standard compulsory kiss goodbye in the morning since the decline in his interest. I’ve told him I didn’t want to have children until we had fixed our relationship, because I wanted my kids to grow up in a house where there wasn’t resentment just boiling under the surface. This pregnancy was unplanned, but because we’re getting older, I decided to keep it and he is thrilled. Now things feel more urgent. What do I do?
This sounds really tough, and I’m sorry that you’re going through it. The absence of firm answers can be painful, and when they are actively withheld from you, as I suspect they have been, it can feel cruel. A lot of what you say resonates with me. I was in a relationship with someone whose libido didn’t match mine, and I tried and tried to get to the bottom of it (at several points pleading with him to just tell me he wasn’t attracted to me, as my thirst for closure became a fixation). But even through conversation and counseling, I was never able to suss it out. We broke up; he got to keep the answer.
Some differences are irreconcilable, though I understand wanting to find a solution and why doing so is particularly crucial at this juncture, since you’re about to be parents. It does seem that there is more room for discussion: You say you’ve had “endless conversations” (for years now, right?), and yet the best you can muster to explain what’s up with him (and I think something is definitely up with him) is that “he probably has a lower libido than I do.” If this uncertainty can be attributed to your dissatisfaction with his answers, I get it and I relate. However, if you are uncertain because his answers are anything less than definitive, you have a communication problem on top of a sex problem. (No big shock there—they often go hand in hand.) Maybe he’s not really sure what’s going on with him, but this has been going on long enough that he’s had adequate time to examine himself. Perhaps he’s avoiding that self-assessment, and that’s another problem. You may be out of your depth here, and so I advise couples therapy. I hope you can figure something out, but if you don’t, you’ll be OK. I never got my answer, and I’ve long stopped caring.
Dear How to Do It,
I wanted to pose a question to Rich, in reply to the conversation about the fellow who would only date post-op trans women. I wanted to reverse the situation. Would you find it difficult to date a pre-op trans man? Would you be comfortable being with a man sexually who had a vagina? See, I’m a trans man, and it’s a big ordeal trying to find people to date who “go for” our often-unique genitals. Some of us have no penis. Some of us have a micropenis from metoidioplasty. Some of us have large, usable phalloplasty penises. We choose what feels right for us. Most of us can’t afford to choose anyway. When sexuality gets reduced to base genitals, guys like me fall into a gray zone.
Thanks for this question—it allows me some clarifying space. I don’t know if I would find it difficult to date a trans man, because I haven’t yet done so. (Based on feedback I have received from exes as well as my current boyfriend, though, he would almost certainly find it difficult to date me.) I’m not dating, per se, at the moment—I’m in a committed open relationship—so I think the more relevant question to my current situation is whether I’d hook up with a trans guy. I haven’t done that either, but I’m open to it. There are trans guys I’m attracted to, I’m not intimidated by vaginas (despite not having been in the immediate sexual vicinity of one in nearly 20 years), and it seems like it could be hot. I’d say I’m firmly curious at the moment, not necessarily actively pursuing anything, but ready for what comes my way. I wouldn’t want to make anyone feel uncomfortable or as though they were a prop in my exploration, so I’m proceeding cautiously.
I realized that I could be open to this after considering it closely, a process not unlike that which led me to bottoming. For some time, I thought I could never do that, and then after I put considerable effort into it, I realized I could, and now I can’t imagine a life without both topping and bottoming. I believe that people are into what they’re into, but I also believe that people are potentially capable of more. The chat with Stoya that you referenced received some feedback (in this Andrew Sullivan column, for example) that suggested I was driven by performative wokeness to dictate sexual standards. That isn’t it at all. My prevailing philosophy about desire is that it is complicated, with very little data attached to it. We can only trust people when they say what they’re into, and no one is obligated to have sex with anyone, ever. But I also know enough about sexual racism to understand that bigotry can manifest in partner selection, and I know a little bit about trans men’s experiences to understand that rejection in the sexual sphere is often coupled with overt transphobia. I’m not going to ever tell a dyed-in-the-wood cocksucker who lives to service or a power bottom that he needs to start eating pussy, or else. But I’m always going to use this space to ask people to think more about what they believe they know about themselves, especially if they are interested in making their communities more compassionate spaces. The world is changing. There are gay guys who five or 10 years ago never thought they could share a bed with a person with a vagina, and now are. Perhaps someday soon, I will be one of them.
I’ve had so many good experiences from trying new things sexually; if I’m evangelizing anything here, it’s not any kind of limitation but the expansion of pleasure.
More How to Do It
I live in an apartment with stereotypical “thin walls,” with frequently noisy neighbors. This isn’t a complaint. I actually enjoy hearing them have sex and commonly masturbate while listening. I recently had a friend over, during which time we overheard the neighbors going at it. My friend commented that it must be so annoying to have neighbors like that, but I confessed that I enjoyed it and would sometimes masturbate to it. My friend was very offended by this—she thought it was a massive invasion of the neighbors’ privacy and equated it to hiding in their closet. I disagree. Have I overstepped, or am I in the clear?