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Dear Breakup Girl,

I'm worried about putting myself into a situation that may be summed up as "a world of hurt," but I am equally concerned that if I don't, I'll always regret not giving it a shot. So, here's the situation. I met and fell, in the hard and hopeless way, for a guy about five years ago(!). We had a great little relationship going for a couple of months, but I always felt that I was far more interested in it being a first act to a really long play than he was.

He had to move shop several thousand miles. He asked me to go with him, but was mum about why exactly this seemed like a good idea to him. He was very chummy about the whole thing--"It'll be so much fun!" We were both very geographically flexible at the time, so I ended up agreeing to go, figuring I'd see where it led me. At the very last moment fate intervened and put a decisive, completely-out-of-my-hands, stop to my moving along with him.

Three months later he called and suggested I come out for a visit. I was not quite as flexible at that point and asked for some clarification of exactly why I'd be picking up stakes and draining my resources. His answer was a sort of appalled silence followed by an explanation of his (unencouraging) feelings on the viability of long distance relationships.

I decided not to go and pretty much regretted it for five years. I'm going on the "you never know..." concept. We remain in touch in a friendly but pretty unemotional way. He drops me a card at Christmas mentioning his "great girlfriend." He writes me now and says he wants me to meet him in yet another location for a holiday and then will stay with me in a passing-through sort of way for a couple of weeks before becoming geographically unviable for at least another year.

I really want to go on this vacation and would love to get some resolution on the whole situation. I've never been able to get him out of my mind and heart completely. I have yet to meet the guy to whom I don't compare him, and we're talking five years here. So, what do you think is in his head? Does he just want a nice tropical lounge avec girl or is he maybe in something of the same boat I am and wants to see what we're like together all these years down the road? I want to go with an open mind and no expectations, but I know that if it turns into a true buddy holiday I'll be really upset. Am I being obsessive or do I have a chance?

Advice for the hopeless?
--Still Hanging

Dear Still Hanging,

Ah yes! An all-expense-paid vacation in Hurt World! IF YOU PROMISE ME THAT YOU THINK IT WILL HELP, let him hotel at your house for those few days, and see how it feels. Holidays, on the other hand, are rarefied circumstances that I doubt will give you a good/accurate read on any non-vaca future. In any case, apply SPF 50 liberally to your heart; and make sure you're not relegating to Christmas-card status the guys who ring in real life.

Love,
Breakup Girl

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