I matched with my ex's ex, but we're still friends. How should I approach setting up a date?

Masami Hosono
they/them
Hair stylist and founder of Vacancy Project

Hmm this is an interesting question! I think it really depends on the situation and relationship you have with your ex. Let’s say you’re both on very good terms. You’re the type of friends that talk once a week. If that’s the case, I would immediately go to them and say something like:

“Hey, I matched with someone and think they’re cute. But, they’re your ex. How would you feel about me going on a date with them?”

Asking my ex how they feel keeps things open and friendly for all interpretations! However, if you and your ex are friendly but not necessarily super close, I would probably say: “Hey, just wanted to let you to know, I matched with your ex and I’m going on a date with them.”

So, when it comes to going on a date with your ex’s ex, I think the trick to avoiding any awkwardness is just being super transparent. Because, WHO KNOWS! You might really get on with your ex’s ex and want to be partners in the future.

No matter the situation, keeping it light, honest, and clear with all parties involved is the way to go. 

Follow Masami on Instagram and TikTok.

Submit Your NFAQ

Have a Not-so Frequently Asked Question on your mind? Ask away. 

.