Is it time to couple up with my friend?

Our system was down most of the day yesterday. Clearly.

But today we return from an unexpectedly long Labor Day Weekend with a new letter. And you can send your own new letter (all relationship questions welcome) to [email protected] or fill out this easy form, please. 

Hi Meredith,

I have been friends with this guy since freshman year of college. We considered dating in the past but we decided that we weren't ready for that step, and the both of us dated other people while being friends. During our final semester, we got much closer and it was clear that he was into me (though he was casually dating other people during the semester, as well). I didn't address the potential of dating because we were both moving away from each other for four-plus years and I didn't want to do long-distance.

At the end of the semester, he told me that he liked me but agreed that he didn't want to do long-distance or have a serious relationship at this point. My plans have shifted, so now we might be able to reunite in a year or so. I would like to pursue a relationship with him but I don't want to mess up our friendship. My issue is that he never seriously asked me out; he told me he liked me but never went that next step of pursuing a relationship. Should I take his never seriously asking me out as a sign that he doesn't actually want to date me? Thank you!

– Bad Timing


He never asked you out because the two of you discussed the possibility of a relationship and decided – together – that the timing was off.

As for your question about now, I guess I'm wondering if you want to start a relationship with any distance on the horizon. Yes, you have years of friendship as support for this, but romance is a new beginning. If the two of you have time to try life as a couple before you leave, that's one thing, but if you want to hit the start button as you go, it's a much bigger risk. It's very possible that the two of you could date for a month in person and decide, "Eh, we were better off as friends." Do you want to spend a whole year waiting to see if that's true?

Also, he told you he didn't want to have a serious relationship at this point. Are you open to something that's more casual for a year?

The answer might be yes, and only the two of you can decide what risks you want to take and how much energy you can give a relationship when you'll both be having so many other new experiences. But this could be a question you revisit in a year, when there's more information and less distance.

Waiting does seem to be the most practical option. But again, I'm outside looking in. If you really want this, ask how the new timeline changes how you both feel about the options. Be clear about what you want. He hasn't made an ask, but … you haven't either.

– Meredith

Readers? Does the new information change the answer here? What about the formal ask? Wait a year? Advise, please.