More than friends?

As a guy, I have been in the same place several times, and I wish I had some amazing advice for you. All I can say is go for it. I know it is far easier said than done, but as I look back I greatly regret never saying anything when I was in the same situation. In retrospect I realize that we were such good friends that had she felt differently, it may have been akward for a short time, but then it would have been forgotten quickly.

"Regret for the things we did can be tempered by time; it is regret for the things we did not do that is inconsolable."

Yeah, this is kind of tricky. If he's going out with you to all these different places, he may like you as more than a friend. However, it's tricky because you don't want to lose him if he's not into you like that, so I can understand your predicament. Personally, in order to get a general idea of where you stand with him, I would think that if you start flirting with him, you may get an idea of where he's at. I would start off gradually and then lay it on a bit heavier as you go. Watch his reactions. See if he responds to your flirting or if he brushes it off or if he gets scared. If he brushes it off, it may only be because he may think that he's imagining things, but if he gets scared, it may be an indication that he's not into you in that way. However, if he responds to your flirting by flirting back or by becoming more romantic or more into you, you will know that he enjoys your flirting and is interested in you in "that way." Those are my thoughts, but there may be other methods that work also. I wish you good luck! :)

Guys are easy as hell, he likes you. he is probably to scared to make a move just like you. I have had heaps of chic mates who are nothing more than mates, but had one asked me to step it up I would have said yes, even if I didn't expect it.