Juan Miguel, 30

Well, the friends-to-more angle is always a bit tricky. How well do you know him? Is he completely honest? Does he see someone else at home? Could he be gay? If all your answers are positive in this regard, then you have to ask yourself is your friendship strong enough to withstand a rejection (not that he's going to, necessarily)? If it's solid, and you fear asking him directly, then hook up with him and with some grace and subtlety, make some sort of physical contact. Touch his hand/arm, something like that. If he doesn't respond, then no he's not interested. A girlfriend of mine once just touched my hand, with her pinky, once while we were out having a drink....worked like a charm for her!! LOL. My guess is he'll respond, guys can be shy about this type of friendship-relationship thing too.