I’m an 18 years old and I like pushing my boundaries in all aspects of my life. So, in a sort of social experiment, I joined a dating app. Suddenly this 37-years-old guy tells me that him and his girlfriend want to have a threesome. It seems both exciting but also like a bad idea. My first time was sort of emotionally painful, as the guy just acted like it was Ibiza even though we were neighbors and went to the same school. So I really want to avoid being hurt by sex again. What do you think?

To threesome or not to threesome—the modern slut’s dilemma 🙂

In order to answer this question, we have to ask: Why do people get hurt by sex? A common reason is that someone’s expectations of a sexual interaction aren’t met. For instance, with your neighbor, it sounds like you wanted or expected something more meaningful to evolve from your sexual experience, and when it didn’t—because he apparently just wanted sex, and your expectations didn’t align with his—you felt rejected or used in some way. That’s totally understandable; we’ve all been there. But this is why it’s useful to be as realistic and transparent as possible—both with yourself and with your partner(s)—about what you expect to get (or not get, yikes) from a sexual encounter.

With the regards to the threesome, here’s my take: A much older couple wants to have sex with you because they think it will be a fun, novel and sexy experience to fuck a cool young girl like yourself. It’s very possible—likely, even—that they will have sex with you one time and then not want to continue sleeping together. And that’s fine, so long as you’re doing it for the same reason: i.e. you want the novel, yolo experience of fucking a much older couple one time. And while of course you should expect them to be nice and caring during your date, you shouldn’t expect this sexual experience to turn into something more. They might not even want you to sleep over—not in a mean way, but it might cross an intimacy/emotional boundary for them to have a third person spend the night in their bed. But if you fully understand that, and are turned-on by the idea of being the Lolita, and probably being worshiped by this couple for a night, then yes, I totally think you should get threesome’d.

If you think you’re down, why don’t you suggest meeting up with them for a drink or tea one day, and see if you like them IRL before making the decision? This would also be an opportunity for you to all to talk about your expectations and boundaries. And remember: at any point, you can always leave! But if you like them, you can go for it, and then you’ll have a cool story about being double-teamed by a couple twice your age to tell at dinner parties.