Is it a good time to tell him how I feel?

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Dear Meredith,

I am in my early 30s, have a robust social life, and a pretty great career. But I haven't been in a relationship with a man that I truly loved or connected with for five years. And I really want that connection.

I have a friend I met in college, we instantly connected, and have remained good friends ever since – close to 15 years. He is now best friends with my younger brother, too. We are basically family. But I never thought of him romantically and we would always talk about our exes, failed dates, etc. However, in the past few months (and upon the encouragement of my sister, aunts, and mother) I have started thinking about him romantically. He checks all the boxes, is loving, kind, passionate, political, and a feminist. But I haven't said anything to him, nor have any of our mutual friends.

I thought COVID would be a good time to really explore another side of our friendship but he wasn't very responsive. I don't know if now that I'm thinking of him as more than a friend I'm more sensitive to when he doesn't reply to my texts, but that's how I feel. I am wondering if I should make any effort to let him know how I feel or just let this one go and focus on meeting someone in the already limited pool of men who leave much to be desired.

Oh, also, we live in different cities so hanging out in person is basically impossible, but I intend to move to his city by 2021. I was going to move there this summer but COVID kind of ruined all the things.

- to do or not to do


This is a tough one. Yes, it's a great time to explore a new relationship, especially with someone you already know. But it's not so great if that person is far away, outside of your bubble. This is not the moment to be traveling around, making visits.

Also, if you disclose these feelings right before you move, there might be a lot of pressure on both of you to behave a certain way when you get there. Maybe it'll feel like any relationship has to be instantly serious.

Still, you're good friends, and I'd like to think that means the two of you can survive ambiguity, embarrassment, and some awkward conversations. If you're feeling pretty sure about your desire for more, you can tell him you’ve been thinking it for the first time. Don’t tell him he checks boxes (that's not the sexiest intro). Ask him if he's ever thought about you that way. If he ever could.

Keep the stakes low. You're simply planting a seed and asking some questions. Really, you don't know how you'll feel when you see him again. There's a reason you spent 15 years not pursuing this man. It's possible that when you're in his city, you'll remember why. Aunts and moms are powerful people, but they don't know everything.

I do think that for some, this is a great time to disclose crushes, even if it turns out they’re not reciprocated. It’s flattering to hear that someone thinks you're great, and no matter what happens, everyone has time to think about it – or get over it – in the privacy of their own homes.

Unless they're roommates. Then it's more complicated.

– Meredith

Readers? Have you disclosed romantic feelings to anyone during this time? Should this LW?