Dear Elsa,

I have a great guy friend that I’ve known for almost 9 years now.

We’ve maintained a pretty open friendship where we can talk to each other about pretty much anything – including current relationships. About 6 years ago, he admitted to really liking me and told me that he had for quite some time. Because he’d been drinking that night, I wasn’t sure how to respond and brushed it off.

Of course, afterwards things were a bit awkward. We never brought it up again so things just settled back to how they were before. The thing is, I get the feeling that he never got over his feelings for me. And now that we’re of marrying age, he’s always describing to me the kind of woman he wants to marry – and that woman sounds a lot like me.

He’s already planning for us to go sailing down to Mexico when I’m back in town next month. He says it’s for our “ten year anniversary.” Needless to say, his girlfriend will not be joining us. All these things makes me wonder. And I feel torn between what I should do.

Should I risk my friendship of nearly a decade for a relationship based on pity? I suppose pity is a harsh word because he is a really great guy. I could see myself falling for him, but I’m afraid I only feel this way because I know how he feels about me.

This is all so “When Harry Met Sally”, isn’t it?

Confused,
Possibly Sally