Is booking a gigolo cheating? The real answer

The answer doesn’t depend on what happens. It depends on who knows. Cheating, by definition, is something you do behind your partner’s back. If it happens with their knowledge and agreement, it isn’t cheating, however uncomfortable the word keeps sounding.

That’s the short version. What matters in practice is the grey zone in between, and that’s what the rest of this piece is about.

Why the act isn’t the line

Couples who come out of this well have one thing in common: they decided for themselves where their line is, instead of borrowing it from outside.

For one couple, kissing someone else is the line, and everything after that is negotiable. For another, sex is fine but falling in love is the red line. For a third, the line is secrecy and nothing else.

None of those three is objectively more correct. What they do share is that they were said out loud. A line that’s never named only becomes visible the moment it’s crossed, and by then the conversation is a fight.

Where it goes wrong: half-knowing

The most common situation isn’t secrecy, and it isn’t full agreement either. It’s the in-between.

“He knows I’m doing something, but not what.” “We talked about it once and it never turned into a no.” “I think he suspects.”

That isn’t consent. It’s putting off the same conversation, with the added problem that you’ve now convinced yourself it’s settled. When it comes out later anyway, the conversation is no longer about what you did. It’s about the fact that you thought you were allowed to.

One thing matters more than the rest: explicit isn’t the same as uncomfortable. The conversation is shorter than you think, and it’s a lot shorter than the version you get if you keep putting it off.

Having the conversation

Start with what you want to feel, not with what you want to do. “I want to feel desired again” opens something up. “I want to book a gigolo” is a proposal someone has to say yes or no to, and that turns one of you into a petitioner and the other into a gatekeeper.

Say what it doesn’t mean too: that you don’t want to leave, that you don’t think he’s failing you, that this sits alongside your life together. That sounds unnecessary, and it’s the part that saves the conversation, because it’s what the other person actually hears.

And pick your moment. Not right after sex, not right before sleep, and not when something else is going on.

If the answer is no

Then it’s no, and going ahead anyway is cheating. That’s not meant to moralize. It’s simply what the word means.

What you have then is a difference in what the two of you want, and that’s a real problem you have to solve with a real conversation. Sometimes with help. The one thing you don’t solve by arranging it elsewhere is the reason you wanted it.

If the answer is yes

Then something starts that asks more of you than secrecy. Deceit only asks for silence; this asks for agreements.

What does and doesn’t happen. Whether he’s there or not. Whether you tell him about it afterward, and in how much detail. Whether it’s a one-off or not. What happens if one of you has second thoughts halfway through.

Those agreements aren’t romantic, and they don’t need to be. They’re there so that during and afterward no negotiation is needed, at exactly the moment when negotiating goes worst.

What I do about it

I ask about it in the pre-talk, even when no one brings it up. Does your partner know, and does he want it? Those are two different questions, and I ask both.

If I sense the answer doesn’t add up, I name it. Not as a moral judgment. It’s practical: someone who doesn’t really want this shows it on the night itself, and then it’s no good to anyone. That’s one of the few reasons I turn a booking down.

What couples actually get out of it

The unexpected result is that the conversation often does more than the evening does.

In the run-up, a lot of couples talk more openly than they have in months: about what they miss and what they’re afraid of. That conversation would never have happened without a reason to have it, and it stays with them even if the booking eventually doesn’t happen.

How a date like this actually runs is covered under Couples. And if what’s really bothering you is whether it’s strange to be thinking about this at all: it isn’t, and there’s more about that under Still hesitating?.