How to Do It

Older Guys I Sleep With Keep Giving Me Gifts

Is it wrong to accept them?

GIF: 20 year old man questioning in bed.
Photo illustration by Slate. Photo by VladOrlov/Getty Images.

How to Do It is Slate’s sex advice column. Send your questions for Stoya and Rich to

Every Thursday night, the crew will answer one bonus question in chat form. This week, gift etiquette.

Dear How to Do It,

I’m a 25-year-old gay guy. I’ve been out and sexually active from around the age of 16, and I’ve had one yearlong relationship in that time with a guy around my own age. I’d say I’m the “old-fashioned” type—marriage and monogamy and all the rest. That’s not to say I’m a prude; I hook up often.

Good looks or a chiseled bod don’t play too much of a part in who I find myself attracted to. Often I’ll see “older” men. The trouble I have is that I often find that these guys (40+), after I have sex with them a number of times, develop the habit of basically supporting me—buying me alcohol, cigarettes, dinners, movie tickets, etc. I don’t want to feel like I’m exchanging sex for these things, and I find it unattractive that many of these men will only sleep with guys 15-plus years their junior. I’ve never asked any of these guys for any of the gifts they’re throwing at me; oftentimes, I’ve actually made it pretty clear that I feel like I’m inadvertently selling myself to a degree and it’s uncomfortable. But I’m also hypocritical and accept them without much argument when I’m really broke (which is pretty often).

Am I lying to myself about my intentions? And how can I turn around after a month of accepting these things out of desperation and then draw a line without feeling like I’m just using these guys?

—Not Spoiled

Stoya: This letter has me wondering about the social norms around this kind of treatment in gay circles.

Rich: It’s hard to say. Casual intergenerational sex is definitely not taboo. And in those cases, you’re spending a lot of time with someone up close so, beyond sex, life stuff comes up. Stuff like, “I’m hungry.” In a certain way, it makes sense to pay for things for someone if you have a surplus of money and they’re broke because they are just starting their lives. It’s a slippery slope, I guess, but I’ve definitely felt a kind of dad pull to pay for guys’ meal when they’re in their 20s. It’s just practical. I have some money, you don’t, so here’s some food for both of us. I’m no major dad, so it’s more casual than supporting someone.

Stoya: This all sounds exactly like my experience in the heterosexual world, though I’ve felt a little squicky about it at times myself.

Rich: I don’t think it’s particularly unique, but it may be a bit more common among gay men of a certain income bracket and lifestyle that allows for casual sex. In general, I think it’s a sort of pan-cultural phenomenon.

Stoya: It’s generous. That’s an attractive quality in a person. To a certain degree.

Rich: The second guy I ever hooked up gave me money for a cab back to NYU. And I felt squicky about that. If some rich guy in a Chelsea penthouse wants to buy me pizza, OK, sure.

Stoya: Do you know what squicked you?

Rich: The placing of money in my hand felt really transactional … and then I was like, “I’m worth waaaaay more than $20.”

Stoya: Hahaha.

Rich: What squicked you?

Stoya: Different things with different people. One kept buying me things I didn’t want and, in one case, didn’t have room to store. Another would buy me nice clothing when he did something hurtful instead of an apology.

Rich: Oh God, that’s like, straight-outta-the-’80s capitalism: We don’t communicate, we buy things.

Stoya: They were both significantly older.

Rich: The guy who didn’t apologize just sounds dysfunctional to me.

Stoya: Yes.

Rich: Sad in its specific way.

Stoya: So compared to that, the guys who take care of the check at dinner or bring a decent bottle of booze—basically what the writer describes—seem nice, reasonable, and I don’t know, gentlemanly?

Rich: Given certain obvious disparities, the dick move is not to do that, but it does seem like our letter writer is getting a little bit more than that.

Stoya: But, like, only a little.

Rich: Maybe it’s that these relationships are sex-buddy arrangements that don’t necessarily sound like they’re going anywhere. But overall, it sounds to me like while there things that make him uncomfortable here, his behavior suggests that he’s more comfortable than not at the moment.

Stoya: I wonder if he’s considering the emotional and intellectual contributions he makes. It isn’t necessarily a 1:1 sex-gifts exchange. Or if it is, it’s a little more complicated.

Rich: A great point. I think of his dilemma as the one a mostly healthy eater might have with a piece of cake. You know the cake is full of sugar that’s bad for you, but you’re hungry for it, you eat it, and then you feel remorse about it. That sucks, but you picked up the fork.

If this is such a burden, you have to be very firm. Don’t accept the gifts. When you want dinner, go home and eat your supermarket ramen. Or you’re just going to be living in mild discomfort.

Stoya: I think there’s mild discomfort either way (being often broke), and he needs to decide which flavor is more in line with his ethics and who he wants to be as a person.

Rich: It’s worth checking in on what’s making him feel like he’s selling himself. Is it learned by messages in our culture? I mean, I don’t think “selling yourself” as a concept is evil.

Stoya: I see nothing wrong with selling your sexuality, but it seems like he’s got some conflict going on around it.

Rich: Are these feelings arising because of negative attitudes toward sex work? If so, it may be worth examining that.

Stoya: For sure. There could be some bigotry at play here.

Rich: I don’t mean to sound mocking or like a cartoon sketch of a human in a broadly drawn version of Vegas, but that line in Showgirls—“sooner or later you’re gonna have to sell it”—is looping in my head. A lot of us sell parts of ourselves, and there are no shortages of ways to do that deemed “acceptable” by society.

Stoya: And what was marriage for a good few hundred years there?

Rich: Right! I mean, technically he just gave us part of his self for free when he wrote in!

Stoya: And we’re profiting from it, along with a company.

Rich: Exactly—while selling microdoses of our identities and experiences. These lines, they blur. When people like you, they buy you stuff. It may get excessive, or weird, or may just mean that you don’t have to eat boiled hot dogs tonight.

Stoya: It’s one of the perks of being a young adult. I’m having one qualm. Is he having sex with the guys who will only sleep with guys 15-plus years younger that he describes himself as really unattracted to? Because then he might actually be lying to himself somewhere.

Rich: Yeah, it seems like he’s suggesting that. At what point does the boner die? When they specify their exact taste? What would be the point in doing that, anyway? “Just so you know, you fall into my rather narrow definition of an acceptable partner. You are no mere object to me—you are data.” I think ultimately, our writer just has to practice being assertive. If these arrangements prove too burdensome, you state your rules and you live by them, and anyone who doesn’t like it can pound sand. It’s probably more difficult to change a situation that you’re already in than it is to start afresh with defined rules.