Hi Meredith,

A few years ago, I met a guy through work and we’ve kept in touch ever since. We live on opposite coasts, but every time we are in each other’s cities we meet up, and we’ve always clicked. He’s around 40; I’m 31. Over the past six months he’s been calling or FaceTiming me every single day, sometimes more than once a day. We’ve grown incredibly close and have talked about anything and everything you can think of – except our past relationship history and current dating (although we have both said we are single). As you can imagine, I’ve developed intense feelings for him over the past few months.

However, I’m struggling with our relationship. It’s gotten to a point where I feel like emotionally, I have a boyfriend, but we have never discussed our feelings for each other. I go out with a different guy and all I think about is him. I’m at the point in my life where I’m ready to settle down and make something happen. Long-distance doesn’t scare me either; we both have flexible professions and I believe it could work quite well.

I struggle with whether I should ask him how he feels about me over the phone or if I should continue to build my relationship with him and wait until we see each other in person before confronting it.

I don’t want to put the pressure of a relationship on us without spending more time together in person, but we can’t easily plan trips around each other when there’s this giant elephant in the room. So what should I do?

– A Torn New Yorker