If you’re into Ann, have maybe thought about kissing her, and suspect you could have fun being alone with her, say yes to the date.

Sure, it’s a risk to the friendship – and maybe the friend group – but that’s part of the dating experience. A date can wind up being awkward and weird, but there’s also the potential for it to become something wonderful.

Maybe you’re feeling “whatever” about Ann, but the fact that you wrote this letter tells me you’re curious, at the very least.

The thing about her judgement and “just break up” advice is that it’s very easy to tell other people what to do while watching from the sidelines. Trust me. I sit here doing that every day. Ann might have a different attitude about her own relationships. She might learn a lot by becoming the main character in a love story.

Sometimes, when I’ve been single for a long time, I decide that my friends’ relationships should be perfect for them – in all ways. Then I remember that our own friendships aren’t perfect. We’re always making mistakes, learning, evolving, etc. Ann could figure out that even the best, most respectful romantic partnerships are messy – because we’re all adjusting as we go.

We don’t know what Ann is up to or how she’ll behave, so this really comes down to your desires. Again, I suspect you want to try this – for a date, at least. If not, that’s fine too. But I assume you wrote this letter for a reason.

– Meredith

Readers? Worth the risk? Thoughts about how Ann talks about relationships?