How to Do It

I Only Date Men Twice My Age. I Think I Know Why.

A man looks at an older man's silhouette.
Photo illustration by Slate. Photo by christian buehner/Unsplash.

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 30-year-old gay man. I have two years sober, and I’m really wanting to have a proper grown-up relationship.

In my late teens/early 20s, I was poor and had little support, and I did some light Craigslist hooking when times were tough. For the most part the sex work was fun and a little exciting, but it was a short-lived period of my life. However, since then, I have developed a preoccupation with older men. From porn to casual meetups, older guys are my go-to. My one serious relationship of the last decade was with someone twice my age.

I think intergenerational romancing can be a great thing, but I’m not sure that mine is always coming from a healthy place. More, it’s comfortable. I think some of the allure is getting off on being desired, and part of it is that there’s just less expectations/pressure; I feel a sense of control over the situation. Dating guys my age feels scary, but I’m not unattracted to them. The only times I’ve developed serious feelings has been for guys my own age, they have been straight or not out, or not interested, which I’m sure is a whole other can of worms. I really have to force myself to go on “date-dates” (not hookups) with age-appropriate guys, and I get so nervous beforehand. I start thinking if I’m this nervous, then it’s not right—maybe I should just stick with dating older.  But on the other hand, maybe the nervousness is something that needs to be worked through. Is a preoccupation with older guys something I need to try to get over? Or give in to? Or is there an option in between?

—May December

Dear May December,

I don’t think that easy is necessarily unhealthy. If the comfort of reduced expectations and being the pretty young thing in your arrangements allows you to enjoy a relationship and its attendant aspects like sex, it’s a useful thing. Having a type need not be an entirely unconscious, ineffable phenomenon—you can have valid, prosocial reasons why you prefer to spend time naked with older guys more than others.

But I think the most crucial thing to keep in mind here is that your go-to dynamic cannot last forever, because youth is fleeting. The transition from twink to daddy isn’t always pretty.

I think you have to ask yourself why spending time with guys your own age is so nerve-wracking for you. Is it the fear of rejection that you perceive being more likely coming from younger guys? If it’s that, realize that rejection is a huge part of dating (and human interaction in general) and going through it can help you build character. It can teach you about how you come off to other people, and it can even be empowering, like when it finally dawns on you that you don’t want to be with someone who doesn’t want to be with you anyway.

If it isn’t rejection, per se, but you can’t figure out where your anxiety about dating guys your own age is coming from, enlist the aid of a therapist. There’s a chance you’re overthinking this, attempting to find a problem where there isn’t one. Maybe you like older guys, that’s your thing, and that’s that. But your distress suggests an unresolved issue that I believe you’d be better off excavating. In the meantime, the in-between option that you’re wondering about is to force yourself out of your comfort zone and date guys your own age, investigating whether familiarity will instill comfort (it often does). Fake it till you make it, as they say.

Dear How to Do It,

I have been married for almost a year now to my husband. Prior to this, we dated for a little more than three years. Long story short, he was married before and got a divorce because he cheated on her. He has been wanting a threesome for a long time even with her, and said that’s why he cheated in the first place. Before we got married, I told him I didn’t feel comfortable with having a threesome either, and then thought hard about it because he threatened not to marry me unless I was willing to do this. So I said OK. Well, it’s been almost nine months that we have been married, and I can’t bring myself to do it. He has threatened divorce multiple times and has left me crying late at night while lying in bed thinking what I’ve done so wrong. He now feels he is stuck with me and does not feel sexually attracted to me anymore. He continues to bring this up all the time. I don’t know what to do anymore. Should I try it? Or not? We are both Christians, and I don’t feel like it is the right thing to do. I have had a threesome in my past, but I also wasn’t in a relationship and at that time it made me jealous even with someone I trusted. Can you help me please?

—Three’s a Crowd

Dear Three’s a Crowd,

I hope you’re learning why honest and direct communication is so important, even if it means called-off engagements. Your future husband told you his terms, and you agreed to them. I think you bear some responsibility here, but you also deserve compassion. While I don’t know the exact tone of the conversation during which you agreed to threesomes, you say he “threatened” to not marry you, and so it seems possible that you agreed to threesomes under duress. That’s no way to map out the terms of the relationship, and it would mean your husband facilitated the poor communication that he’s now holding against you. Elisabeth Sheff, whose 2013 book The Polyamorists Next Door is as essential a text on nonmonogamy as any I’ve read, wrote about the detrimental lopsidedness of such negotiations a few years ago for Psychology Today. She was describing polyamory, which is different than the group play your husband suggested, but I think the advice still holds for any arrangement that deviates from strict heteronormativity:

If the monogamous person has agreed to polyamory under duress, then disaster will most likely eventually ensue. Duress can take a range of forms—financial, emotional, physical, explicit, implied, or even unconscious. Agreements made under duress are not truly consensual because they come with some kind of threat to enforce the desired outcome; if “no” is not an acceptable answer, then “yes” is not a real choice.

If your husband pressured you to say yes, he shouldn’t be surprised that things turned out this way. After all, you voiced your discomfort upfront. But then, unfortunately, you married him. And here we are. I’m not going to recommend that you take part in something that you don’t want to do. Perhaps it would be a way of preserving your marriage. Maybe you’d enjoy it once you gave it a try with him. But even if you did it once, keep in mind that your husband explicitly said that he wanted threesomes to be a recurring feature of your shared sex life. Can you live in such an arrangement? The answer seems to be no. Act accordingly.

Dear How to Do It,

I am a 22-year-old woman, and my best friend is a 23-year-old man I’ve known since high school. When we hang out, it’s always at my place (his is a dump), and he often stays overnight and sometimes for a few days. In the seven years we’ve been friends, we’ve slept in the same bed, even shared a sleeping bag once when camping, and gotten dressed and undressed in front of each other, and there’s never been anything sexual between us—until “the incident.” A couple of weeks ago, we were watching TV, eating popcorn, and drinking lots of beer before crashing around 1 a.m. A few hours later, I woke up to find him on top of me—and inside me. After I shoved him off and yelled “WTF do you think you’re doing,” he said he woke up to go to the bathroom and when he came back and saw me in bed, I looked like Sleeping Beauty and he wanted to wake me with a kiss. And that when it didn’t work, he thought he’d try to wake me with sex. He was laughing, and I told him it was not funny at all, and asked him “you understand the concept of consent, right?” He said he did, so I made him tell me what he thinks it is, and he gave the textbook answer we learned in high school sex ed. I said then you realize that you were raping me, and first he argued that he didn’t, but then admitted that was what it was and said he was sorry.

The next time he came over he said very sweetly, “This time I’m asking, would you like to have sex with me?” I said no and I’ve said no every time he’s asked since. This hurts him, and I understand that because I’ll have sex with anyone as long as I know him and like him. But I still don’t understand what happened—why he suddenly has sexual feelings for me, and what made him think he could just have sex with me without asking. I’ve never heard him say a disparaging thing about women in general or any woman in particular and always considered him a very woke feminist. He’s dated some of my friends, and they’ve never said he’s done anything threatening or controlling. They think he’s a very nice guy—thoughtful and considerate—which is what I always thought too. He’s told me over and over that he never meant to hurt me, and he’s sorry, and why can’t I get over it? I don’t know the answer to that. He asks what he can do to make it better, and I don’t know the answer to that either. Am I making a bigger thing of this than it is?

—So Confused

Dear SC,

I think a lot of people, myself included, would say that you are in fact not making a big enough deal about this. You’re entitled to process being raped as you see fit, and you don’t have to feel traumatized by an incident that would traumatize someone else. But I think trauma, or something like it in the form of an unresolved issue, is gnawing at you, and is why you “can’t get over it.” And I think this guy wants you to get over it more for him than for you: He wants to be absolved by your emotional equilibrium. If you’re OK with what he did, then he’s OK.

That you’ve continued hanging out with him after he violated you is surprising, to put it nicely. My most optimistic read on this situation is that you are immensely forgiving, and this guy should be grateful for being allowed to remain in your life, let alone not being arrested for rape. And yet, he has continued to attempt to cajole you into a sexual relationship, with frustration expressed at your lack of interest and inability to forgive him. True apologies are not contingent on ensuing forgiveness; they are self-contained expressions of contrition that live and die on their own. I don’t believe he’s actually sorry.

As to why a guy who presented himself as “woke” could resort to such a brutal expression of misogyny, well, a good smokescreen isn’t easily identified as such. This is a textbook case of saying one thing and doing another. One can understand certain concepts intellectually but fail to put them into practice when doing so would obstruct from getting them what they want.

Right now this guy is a parasite, enacting harm, demanding forgiveness, pressuring for a relationship that you have established wanting no part of. You want advice? Here’s advice: Kick this guy to the curb, get some counseling, and consider next steps for closure. You don’t have to contact authorities (though you could). Perhaps something along the lines of a restorative justice process would be more useful. No matter how you heal, the more you put up with this guy and his bullshit, the more you run the risk of showing him that you condone his behavior. As things stand, he’s clearly not getting it.

Dear How to Do It,

I am a woman married to a man. We have been together since I was 23 and he was 35. I am now 34, and he is 47. Our sex life in the beginning was good. We had sex maybe once a week, then after a year, maybe twice a month. Then after about five years once a month, and now we have sex once every three months. Lately, we haven’t been having sex at all. I am demi-sexual so I am sexually attracted to people I have an intellectual connection with. He has told me he is more sensory-based: feel, smell, and sight. So I take showers before sex, and I sometimes will walk around in short shorts and a cute bralette or whatever. I proposition him or mention we should have sex once a week and he says, “Yeah!” And then we never do. I’m tired of always being the one to ask about it, and I don’t want to put any more pressure on him. I’m just horny—I’m craving intimate sexual connection and I don’t know what to do. We start couples counseling this week, and I asked him what topics we need to work on so we could both be comfortable. He said sex (of course). I want to respect that, and I will, but I don’t think he understands how much of an issue this is for me. It makes me feel insecure. I’ve gained weight over the course of our relationship, I’ve changed as a person, and I just feel like he doesn’t think I’m attractive or desirable anymore. When I bring these insecurities up, he says that’s not it and he’s just “47 now and his libido isn’t like it used to be.” He has a history of not sharing what he really thinks because he is afraid it will hurt my feelings. I’ve told him I can handle it, and it takes a lot to offend me AND sometimes I will be hurt, and that’s life. Still he says it’s not looks and I’ve offered to spice things up too. We have always been monogamous and because I’m demi I would rather not open our marriage up—I don’t want that connection with someone else, but I want to have sex! I’m horny and confused.


Dear Upfront,

Interconnected as you and your husband are, there are discrete sets of issues here: yours and his. You have reason to suspect that he’s not being as forthcoming as he could be, and I don’t want to invalidate your own read on your situation, but until it is confirmed, these suspicions are mere anxiety. For reasons including but not limited to waning testosterone levels, men’s libidos tend to decline over time, and it takes more than a pair of pompom shorts to reverse that process. Sex also tends to decrease in frequency over time for long-term couples for reasons that go beyond the hormonal as well.

You may be justified in taking this all personally, but then, you might not. I think erring toward the latter will be a useful mindset in therapy, as it will allow you to target and respect his issues with respect and precision, and without getting in the way of them. It’s great that you’re pursuing counseling. Keep an open mind and heart.