How to Do It

I’m 33 and Sleeping With a 19-Year-Old

What’s the problem?

GIF of a man scratching his head while neon ID cards glow in the background
Photo illustration by Slate. Photo by feedough/iStock/Getty Image Plus.

How to Do It is Slate’s sex advice column. Send your questions for Stoya and Rich to howtodoit@slate.comNothing’s too small (or big).

Every Thursday night, the crew responds to a bonus question in chat form.

Dear How to Do It,

I’m a man who just turned 33. When I was younger, my tastes generally trended older—I dated someone for many years who was more than a decade older than me, and I would regularly date people in their 30s when I was in my 20s. As I enter my 30s, however, I’ve noticed that I surprisingly have developed an interest in people who are much younger. I’m dating someone on an open basis around my age, but when it comes to conquests I have found myself seeking out people in their early 20s, and I recently have had a regular thing with someone who just turned 19. Some of my friends are skeeved out by this, and I am also a little surprised by the way my tastes are changing, but I feel it is what it is. (For what it’s worth, I’m still attracted to people older than me, but they’re no longer my primary interest.) Is there some reason to be worried? What should I say to people who seem to judge? I don’t think I’m doing anything wrong, but other people seem really sensitive about it.


—Not a Daddy

Stoya: I’ve dated older and younger. I’m pretty sure you’ve dated older and younger.

Rich: I’ve dated slightly older, slept with considerably older, and mostly gravitate to relatively younger. My boyfriend is three years younger than I am. My last one was 10 years younger.

Stoya: My current main squeeze is nine years younger, and, at 24, has a brain that is literally still developing in a significant way.

Rich: Yes, literally! Do you feel weird about the age difference? (I know the answer to this, but humor me for the people.)

Stoya: Ha. Oh man. I had to run it past four people—my favorite ex-boyfriend, my bestie, my roommate, and my co-columnist—before I felt comfortable proceeding with anything past a single hookup.


Rich: I’m honored to be a member of the board.

Stoya: I also dated much older when I was in my 20s, and a big part of my concern came from having dated people who didn’t understand that I was still developing (not that we aren’t all always developing, but you know—significantly).

Rich: Right, literal brain development.

Stoya: And, frankly, sometimes I forget with the 24-year-old.


Rich: I definitely had issues in the past with younger guys about openness and the general need for me to take control and be a dad; I tend to approach relationships from a more egalitarian perspective.

Stoya: There’s definitely a power imbalance that can develop easily.

Rich: Yes, it felt like it was written into one relationship, and I did a lot of dumb assuming about it not existing.


Stoya: Because we have our ideals! And sometimes that blurs our vision of the reality.

Rich: It’s so true. And I felt like I was being practical at the time, but that was its own fantasy. Realizing that was the real kick in the dick.


Stoya: So I think our writer is probably within the ranges of acceptable and normal.

Rich: It’s not midlife crisis–levels of egregious.

Stoya: But what does he need to keep an eye on?

Rich: We’ve talked about ongoing romantic relationships thus far, but the young’uns are presented here as sex buddies. That’s an important distinction. A no-strings situation with someone younger really can be just that—and not dramatic or damaging. Still, even in a very casual arrangement with someone that you know you have no future with, I think everyone must remain on the same page. There are young people who are just going to bang and bang, and you’re basically just a body number to them, and that’s totally fine. They’d be screwing someone else if not you. And then there are the ones who are inexperienced and quickly jump to wanting more than just sex.


Stoya: An emotionally significant relationship between people who are in very different places in life can be difficult.

Rich: Totally, and in a way you do need to make certain concessions, or at least bring a lot of understanding and compassion, as the person with more life experience.

Stoya: That doesn’t mean the younger person gets to walk all over you or have hurtful outbursts regularly. But it does mean being gentle when they espouse rigid views of the world or lack some empathy for others. (Talking about 20s me, not the 24-year-old.)

Rich: Yes. And you know, I had a little thing with a 23-year-old not long ago, and I was the one with more feelings than him. So it can be a bit unpredictable, as matters of the heart and genitals tend to be. I think in general if you set out to start a sort of sex friendship with anyone, regardless of age, you have to keep sniffing to make sure the terms stay unanimous.


Stoya: YES.

Rich: When one person starts getting emotional in a way the other isn’t, it’s really up to that other to say something and not lead them on, even if it’s passively. Again, this is regardless of age, but particularly important to keep in mind when you’re in your 30s sleeping with someone in their 20s (or 19). Is it way off-base of me to think that this question varies depending on gender?


Stoya: Not at all. The situation has very different optics if he’s hooking up with men versus women.

Rich: Maybe it’s just because I have the model of creepy old man in my head, but I feel like this scenario is potentially a much bigger deal if the younger person is a woman.


Stoya: Yeah. We live in a gendered society.

Rich: Right, which is much more predatory for women—and the younger they are, the more vulnerable, potentially.

Stoya: I do think this is one area where patriarchy is unkind toward men. We aren’t as worried about young men, but they still have emotions, are still vulnerable, and may have fewer tools for navigating their vulnerability. They also may have more difficulty opening up to other young men—their peers—about their inner world. Our writer is directly asking what to say to people who judge, and that judgment will almost certainly be different if it involves a young woman. But—regardless of the genders he’s interested in—this can be an opportunity to check his behavior against incoming criticism. Criticism is an opportunity to take stock.


Rich: That’s a fantastic, really positive way of looking at it.


Stoya: Whatever the intent of the writer, he’s pointing out potential traps.

Rich: Yeah, I think maybe the most honest thing you can say sometimes is “You don’t get it,” if that’s the case and the critics are incorrect in their assessments. You know your life better than someone else. And if the parties in question are just sex partners, you have the option of not talking about them. Unless there’s someone you’re going to be introducing to friends, they don’t have to know.


Stoya: Agreed. If there’s someone in your life who just can’t get over your dating age range, focus on other subjects.


Rich: I think given the writer’s wide preferential age range, there’s no reason to be worried. Narrow taste is always what raises my hackles because it suggests a possible full-time fetishization/objectifying of individuals.

Stoya: Pluralism. I like it.

Rich: If somewhat younger people are just part of the repertoire, OK.

Stoya: Agreed. 100 percent. If he were exclusively dating young people, I’d be concerned about lingering immaturity or predatory behaviors on the writer’s part. But there’s one red flag in this letter that just won’t leave me alone.


Rich: Tell me!

Stoya: He gives a decent amount of detail, but he doesn’t specify the genders they date.

Rich: Yeah.

Stoya: Given the statistics, it is most likely that he’s dating women. It’s maybe a little manipulative not to include the gender. Like, one time someone close to me sat on my couch and said they were considering having an affair. I told them not to. Later, it turned out they’d already been having the affair. I don’t know what the word for that is, other than shenanigans, but really—hiding things from the person you’re going to for advice doesn’t help.


Rich: The fullest possible disclosure helps us help you.

Stoya: So my advice to the writer is to think about what he left out of his letter and WHY he left it out.

More How to Do It

I’m single after nearly a decade. I’ve been dating and hooking up a fair bit. Recently, one man who I had dated and slept with a few times reappeared and began pursuing me again. I responded positively at first but found myself not replying to his texts, and eventually he took the hint, but then asked me: “Just curious, why aren’t you interested? I thought we really hit it off.” The truth is, we did. But I have not replied because I’m embarrassed to have realized the reason is that his dick is small.