Ask iris: "Is it Wrong to Date My Current Hookup's Best Friend?"

Dear iris,

I met someone, and we went on a few dates and got intimate and had intercourse. Recently the dating experience hasn’t been like it was before we had sex. Is it wrong to start dating one of his friends? In my defense, he doesn't know I know they're friends because he never told me.

Signed, Ready to Move On

Dear, Ready to Move On

This scenario is a tricky one. I understand that you're not attracted to the guy you’re currently seeing anymore, and it makes sense you want to move on. I understand why you’d feel like it’s fair game to date his friend, since you can feign innocence and say you didn’t know they were friends.

At the same time, you wrote in this question. That means it felt iffy or even wrong enough for you to ask for advice on the situation. Which, to me, is all the indicator you need to not date his friend. If you have to wonder, then it’s probably not a good idea.

Put yourself in this guy's shoes: if you really liked someone, how would you feel if all of the sudden they started dating your friend? And worse, what if you found out they knew that person was your friend and they decided to date them anyway?

You’d be crushed. And rightfully so. It’s pretty disrespectful.

Look, I’m not sure if you believe in karma, but it seems this situation could lead to a lot of drama. What if starting to date his friend ruins their friendship? What kind of relationship would you have after being the cause of that falling out?

If part of you still wants to date his friend then please do two things:

First, tell the guy you’re currently seeing that you’re not interested in dating anymore. Let him know this in-person. Don’t ghost him. Explain why you don’t think you’re a good match and no longer want to date.

Then (and maybe wait a few weeks for him to process the situation), ask him if it would be okay to date his friend. That way, you can have a clear conscience if he says he’s okay with it. If either of these sounds too difficult to do, then I’d take some time off dating and consider what your intentions are.

Because there are plenty of people to date who are not in this murky gray area. You won’t have to ruin a friendship and potentially break someone’s heart. If you really think this guy’s friend is worth giving a shot, then talking to the guy you’re currently dating shouldn’t be an issue. It’s the respectful thing to do.

Sometimes, we look for permission to do things we know aren’t right. I feel like that’s what was going on when you wrote in this question. Personally, I’d end things with the guy you’re currently dating and take some time to yourself to be single. Then go out there and date other people. If time passes and your path crosses with the path of this guy’s friend, then maybe that will be the time to give things a try. But right now isn’t the right time, and it seems like you already know that.