How to Do It

I Want to Buy My Dying Mom One Last Night With a Stud

Should I tell her I paid him?

A man prepares to give a sick woman the time of her life, as money signs flash in the background.
Photo illustration by Slate. Photos by Getty Images Plus.

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

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

Dear How to Do It,

My mother is in her late 50s and has been diagnosed with an inoperable brain tumor. She tried one round of radiation, but now she is resigned to her fate and doesn’t want more treatment. She is still mentally alert and vivacious. I disagree with her decision, but I respect it.

We are open with each other, and I know that she was dating and sexually active until her diagnosis. As a final gift, I would like to give her one last fling with a young stud. I talked to an acquaintance who is good-looking, fit, and willing to perform for a reasonable fee. Do you think that I will need to tell her he is being paid? Don’t get me wrong, I would absolutely tell the truth if she asked. But this seems like a situation where “don’t ask, don’t tell” is the best policy. Also, any tips for her stud to give her the best possible experience?

—Going-Away Present

Stoya: So, this question.

Rich: A real roller coaster of emotions—sadness and swinging and frustration and orgasming—that spans the breadth of the human experience, from birth to death.

Stoya: It’s really intense.

Rich: Truly. And to the letter writer, I’m so sorry about your mom’s illness and what you’re going through.

Stoya: Yes, and I’m glad the writer is respecting the mom’s decisions and focusing on the present. I’m going to start at the easiest end. Tip No. 1 for the stud: Bring lube. Radiation can affect vaginal secretions, and you really don’t want a condom-burn scenario.

Rich: He should treat her like she’s the hottest woman he’s ever had sex with. I mean, maybe she will be! But even if she isn’t, I hope he worships her.

Stoya: Yes. If the stud is wired toward service at all, this is an opportunity.

Rich: I wonder if he’s a professional sex worker or just … some dude our letter writer knows. Because how do you even bring that up with someone who isn’t in the business of giving women the business?

Stoya: Perhaps it’s an acquaintance who escorts? And is out about it? Which feels like it’d be rare.

Rich: Definite possibility. I’m just saying, if not, finding him must have been a story in itself. Are there any other sort of cancer-specific sex guidelines like the first one you mentioned? Because otherwise, this guy probably knows what he’s doing, assuming he’s had sex before, and he should just do it better than he’s ever done it in his life given the circumstances.

Stoya: There’s some information here, and it’s probably not a bad idea for the mom to talk to her doctor if this plan goes into motion.

Rich: All right, so the other attendant issues. Does the writer have to disclose that this sex has been paid for?

Stoya: My gut says yes, but my brain says maybe?

Rich: Ah, interesting. I feel like, nah, it’s a white lie in the service of making a dying woman feel good about herself. But I’m curious to hear about your rationale.

Stoya: Disclosure is crucial to consent. She can’t cleanly say yes to sex if she doesn’t know the conditions it is happening in.

Rich: This is an excellent point. Is it that you don’t believe that whatever ego boost could arise from her thinking she bagged this stud herself isn’t worth withholding the truth on principle?

Stoya: I think my main worry is the potential aftermath. What happens if she has sex under false pretenses and then finds out? Weighing the likely ego boost against the potential feelings of betrayal—I don’t think the risk is worth taking.

Rich: The risk outweighs the reward. I’m curious as to how the writer planned to pull this off without notifying her what was happening?

Stoya: Exactly. Especially if the guy isn’t a professional.

Rich: Some kind of pizza delivery/UPS man scenario?

Stoya: Or a dinner out where they have to wait at the bar and he strikes up a conversation?

Rich: It seems that it would require him to also be a good actor. Maybe the writer would just say they have a friend who wants to help? In light of what you said, it doesn’t really seem like this would be that much better of a gift as a surprise than as something the writer talks to her about beforehand: “Do you want me to hire a stud for your last hurrah?” It isn’t that awkward of a conversation if you’re already in the position of knowing that your mother might enjoy something like that.

Stoya: There’s a (small!) chance the transactional nature might be a turn-on.

Rich: Yes, I mean, it could be something she always wanted to try.

Stoya: I mean, even just knowing it’s all about you can be great.

Rich: She can be as demanding as she goddamn pleases! It’s her diva day!

Stoya: YES! So there are many pros to open discussion.

Rich: Besides, what if this guy just doesn’t flip her switch for whatever reason? That would be awkward. Ultimately, it seems that not disclosing it is antithetical to the relationship our letter writer has with their mother, given their intimate awareness of her sex life. I can’t imagine that level of closeness with either of my parents regarding sex, but I think it’s cool for other people. I feel the same way about camping or Spam sushi: You have your fun with that, but none for me, thanks.

Stoya: You’re completely right, though—if they can talk openly about sex, and consider hiring an escort as a present, they can totally talk openly about hiring the escort.

Rich: Hopefully the mom is not offended at the prospect, but I have a feeling that she won’t be if she’s as progressive as she sounds.

Stoya: And, like, if she’s going to get offended, it’ll be better than after the fact.