He’s asking what-ifs

Dear Meredith,

About five years ago I made a move for a specialized, two-year training program. While there, I met a great guy who moved from the other side of the country for the same program. We hit it off and dated for about a year, both realizing our love for our respective coasts, and knowing that our "relationship" probably wouldn't develop too far. Once our training program ended, we parted as friends and kept in contact with occasional phone calls and emails. He told me about girls he's dated since then, and vice versa.

Fast forward to last week. We hadn't spoken in a few months, simply because life was busy for both of us. During our conversation last week he said, "It's too bad we don't live in the same area. I still think we're a good couple." I sort of laughed it off and agreed in a half-hearted manner. Personally, I think that line of conversation doesn't get us anywhere and it leaves me irritated (which I've told him before) knowing his job requires him to live on the West Coast, and I LOVE Boston.

The problem came the next day when he texted me, asking if I would dump my current boyfriend (a term I use lightly since it's only been a couple months) and date him if he moved to the same area. I told him I couldn't answer that question, and it's pointless for me to think about unless he's actually moving (which he's not -- and can't). To that he replied, "I just want to know how you feel about me."
When I told him that line of questioning was irritating me, he got upset, called me a tease, and has refused to talk so we can discuss things. I guess I always assumed that our friendship was just that, a friendship and nothing more. But now I'm getting the feeling that he's held onto feelings all this time. Or maybe he's having "girl-trouble" and wants to know he's wanted by someone? I don't know, but without talking to him I can't figure it out.

My question is: Should I continue trying to talk to him about this? Should I wait for him to contact me? Am I out of line to get irritated by those "what-if" questions? This isn't a lost love I'm trying to hang onto, it's what I thought was a friendship with a person I care about. How hard should I try to hang on?

Thanks for your (and all the readers') help!

– Irritated, Boston

He wants to know how you feel about him, so tell him. And maybe tell me while you're at it, because I can't figure out what's going on here.

Do you have romantic feelings that you compartmentalize because of distance? Or do you really just want him as a friend? There are no wrong answers here. It would just be good to know how you feel so you can make smart decisions about how to move forward.

If your answer is, "We're friends, but if he lived down the street I might want more," maybe this relationship too confusing for him to continue. Maybe having you around -- even just on the phone -- is making it difficult for him to connect with other women.

I don't like that he called you a tease, and I certainly don't enjoy his passive-aggressive method of trying to get answers out of you, but he's struggling and wants to know where he stands.

Take some time and think about your feelings. If he lived here, would you want more? How do you see this friendship evolving if you both find other partners? After you come up with some specific answers, send him an email spelling it all out. Be clear about what you want and ask him if he's up for whatever you can offer.

Instead of getting irritated by the "what-if" questions, try to answer them. It's the only way to keep this relationship honest -- and to figure out whether this is a relationship worth having at all.

Readers? Should she answer the what-ifs? What is causing him to ask these questions? If she knows he's never going to move, should she just drop the friendship? Is there a friendship worth saving here? How does she feel about him? Help.

– Meredith