One of us would have to move

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Hey Meredith,

In 2016, after a year of graduating college, I went to Spain to visit a friend. I matched with a guy on Tinder during the four days I stayed there. We never saw each other in person, but we managed to maintain communication for three years. We flirted, we gave support during moments of grief, etc. He was a "more than friendly" virtual friend. He became more my confidant than most people I knew in person.

In 2019 I saw him for the first time in Boston (we agreed to see each other somewhere we both had never been). By then I was still finishing an advanced degree, so we talked about how long-distance just wasn't going to work. Fast forward to today. I finished my degree and am traveling to Spain. My sister is moving there. I can't help but feel I would like to give "us" a real try. However, the only shot I see of us having a real try is if he moves or I move. I don't know if it is even worth having a conversation about it. What do you think? Thanks!

– Traveling

I have a lot of questions about how it felt to be with him, in person, in 2019. Were you attracted to each other? (I'll assume so.) What was the relationship like after that visit? Was he as engaged as he'd been before?

These are things to think about as you go into a conversation about all of this, because yes, it seems like it's worth a talk. I think most relationship questions are worth one conversation, at the very least.

Assuming there are mutual feelings and you've both been longing for more, this might be a lower-stakes time to try this. One of you would be taking a bigger risk to make this happen, but now that your sister will be in Spain, it might be less of a jump for you. Does her being there make this a less complicated move?

He's your confidant, so discuss this with him. If this is a big "no" on his end, at least you'll be able to move on without wondering what would've happened if you'd asked. Try not to put him on the spot with a question he can't answer. Say what you know and work it out together. "I'm finished with my degree and have been feeling like now might be our time to give it a try. Can we talk this through?"

Good luck.

- Meredith

Readers? Time to talk or leave things as they are? Any advice on how to say it? Where do you think they met up in Boston? I'm trying to imagine what restaurant they might have chosen.