Every week, Mallory Ortberg answers additional questions from readers, just for Slate Plus members.
Q. Relitigating a romance: Alice and I have been friends for a very long time. About five years ago, we came close to having a romantic entanglement, but ultimately decided it was best to stay friends.
There was a lot of romantic tension between us for a while after that, but it eventually settled down. However, lately we’ve been spending more time together, and I’m starting to feel that tension again. At first I thought it was just because of a bad breakup I went through last year, but it’s continued even as the pain of the breakup has died down.
I’ve always been bad at figuring out how other people feel about me, so I’m not sure if she feels the same way. Should I bring up the possibility of giving a relationship of some kind a try, or is it best to let our old decision stand?
A: I think I can see how you two have never quite been able to build up sufficient velocity to get a relationship off the ground. I think it’s worth giving it a go now, but it might help if you framed this not as an exploratory conversation, but as an offer.
Instead of “I’m feeling some tension. Are you feeling some tension? Do you think we should revisit the possibility of romance?”—try “I’ve noticed a strong connection between us, and while I know in the past we’ve decided to just stay friends, I think we might have a really good time if we went out on a date. Would you ever want to go out with me?” Give her something to say “yes” or “no” to.
If she’s anything less than enthusiastic, you can put this behind you and accept that, for whatever reason, you two have a little bit of a spark but not enough to ignite anything beyond a flirtatious friendship.
