Is this relationship realistic?

Dear Meredith,

I am a mid-20s med student who is currently seeing a mid-30s divorced executive with two kids. He lives in Boston but travels extensively. Ever since I moved for medical school a year ago, we have been in a long distance relationship. Because of both of our schedules, we haven't spent a lot of time together in person, but we communicate either through phone, text, email or Skype, every day. He is a wonderful, genuine, and caring person who has never made me feel the age difference. We seem to be extremely compatible on a multitude of levels -- intellectually, sexually, and we have similar outlooks and opinions on many things. (He even introduced me to Love Letters a year ago, and ever since, I've thought about writing in). And as wonderful as the constant technological communication is, it is obviously no replacement for actual time spent together. It's been particularly hard for me, maybe because I'm not as used to being away from the people I love as he is (considering he travels so much). Also, I am not certain of where I will wind up working after school. As far as the future goes, how realistic do you think it is to continue seeing each other, all things considered?

– Wishing I Was in Boston

This commitment isn't realistic, WIWIB. And that's OK. Sometimes pen pal-ish relationships with faraway loves are worth having, especially when you're in your 20s and busy with other stuff.

But you seem to have hit a wall with the distance. It's making you sad. That's no good.

My advice is to ask him whether he has a plan for the future. Is the goal to live in the same city at some point? Does he want to live together? Is he just waiting it out to see where you get placed after school? What about his kids? Does he want to have more? Do you? Has he thought about any of this?

Use his answers to make a plan for yourself. And -- for the record -- you're allowed to keep him around even if he doesn't have answers. If you want to Skype him all night long until you get sick of it, that's OK. You'll know when you can't deal with it anymore. Most relationships like this run their natural course. It's just easier to get to the end of the course if you ask him the tough questions. I get the sense that you've been avoiding them. After a year, it's better to know.

Readers? Am I right about the natural course thing? Would she be wasting her time to keep him around until she gets sick of it? Is there potential here? Even if she's back in Boston, is he the right partner? Anyone date someone who's constantly traveling? Discuss.

– Meredith