I’m moving to Milan. He lives in Milan.

Today is Ep. 10 of the Love Letters podcast. It's a big one.

Get your tickets for this weekend's live taping – or for any of the comedy shows. It will be a lot of fun.

I was studying in Florence for a long time. During my last days there, my friend took me out for some fun. We went to our usual bar, and I saw this really cute guy standing near the bar counter with his friends. Later, our groups were sitting near each other, and we wound up having a great conversation. It was a beautiful chemistry. He told me that he was originally form Milan and was just visiting his friend in Florence. After some talking, he kissed me, and it was the best kiss I ever had. We were loving every moment of being together when he implied we should go further, which is when I told him I'm inexperienced and didn't want to do more.

He was understanding and sweet. He said, "You're leaving tomorrow and I am also going back to Milan, we will probably never meet again, and you should be with someone who can be with you.” When we left, he asked for my number and said that if he’s ever traveling near me, he'd love to visit. After I got back home, I was in tears.

It's been four months and he hasn't contacted me, and I don't have his number or any other contact for him. From the very beginning, I was in love with Italy and always wanted to go back, and coming from the design industry, this is the best thing to do. Recently, to advance my career, I was advised to move to Milan, and now I'm actually planning to move to there in a few months. I was just there couch-surfing, planning my move, and I saw his profile there. Since then, I can't stop thinking about him. What should I do? Should I send him a message or just deal with my thoughts? Because I have no idea how he would feel about me being there, or if he actually cares about it or not.

– Here now


You might as well send him a message. If he has a public profile of some kind, there's no harm in saying hi. Keep the message short and casual, though. For now, it's just a hello.

Please understand that if and when you interact with this man, it probably won't feel like it did that first night. He might still be wonderful, but that night was magical for a number of reasons that no longer apply. You were leaving Florence the next day, which means you had a certain kind of "one last night!" energy. Your introduction at the bar felt serendipitous. It was all very "Before Sunrise." Also, he said romantic, loving things before you left, and you’ve been stewing about them ever since. You don’t know what he's been thinking or doing since you met. Four months later, he might have other commitments.

And remember, he didn't say, "If you lived in Milan, we could be together." All he said that night was that you should be with someone who can stick around.

The point is, yes, you can reach out, but please manage your expectations. He can’t offer what he did that night. Neither can you.

– Meredith

Readers? How should the LW reach out?