Kiss on the hand-friend zone?

Dear readers,

My current love interest is a recently former coworker of the past year who I shared quarters with on occasion.*Because we spent so much time together working closely and talking, I know we are friends...but there have definitely been numerous moments of what I believe to be something more. *I've always disagreed with coworker romances, but now that we aren't *I am thinking of*giving us a shot since we have so much in common, are both available and, overall, he's a great guy who compliments my personality well. *(He's a major extrovert with much a more open, honest, forgiving, playful and joking personality than my introverted, cautious, analytical, and serious self.)**However, I have three major reservations to consider. *

First, he has a habit of zig zagging between vague hints and jokes about liking me;**asking me about my past relationships and what I want in a guy; explaining his jadedness and what he thinks he can't have in a girl; and*telling our mutual friend of wanting to meet "hot girls" in front of me (though I suspect it's just to get a response from me). *I have a habit of just shutting down after comments like these but since we aren't dating I just let the comments slide and try to see beyond it the next time around. *Plus, I know he's used to having just friend relationships with girls. **

Second, when we finally made a spontaneous but sincere plan to meet at a bar, I put on something sexy and my best foot forward. *Not long after arriving, he pointed to a girl not unlike myself and explained how he wants someone like her but it seems to never work out with girls he really wants. *He also mentioned that marriage is like suicide and that he's really jaded about finding love. *To my surprise*his love interest of one week arrived an hour later! *That was also the night after*I had just ended it with my latest female love interest*and revealed to him my bisexuality. His response in his drunkenness was utter shock and a tender kiss on my hand. *I didn't know what to do since he was on a date and drunk so neither did I take it seriously nor did I try to laugh it off. He clearly has figured out that I like him and has*tried to have me to tell him that I like him more than once and I couldn't. *I also know I gave some mixed, vague signals since that night and probably ruined any chance of his making further advances.

Lastly, after finally being in the same city for at least a month, I will be living four hours away, again, but without the planned living together situation due to work. *We are both accustomed to long distance relationships and aware of how it stresses it. On the other hand, I have never been so crazy for someone before. And in a week I will be returning with him to our home state and spending many hours in a cramped car and hotel.

Is he a spineless jerk or an incredibly scared romantic like myself? *Should I tell him I like him and risk straining everything due to our distance and my forwardness? If so, before, during, or after the trip?