He's driving me crazy!

[shesahottie86]

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 and he's so wonderful I am thinking of spicing things up. 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 (not a date) 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 drunken response 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, I will be living four hours away, 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 which will be smoking hot from a combination of his good looks and my nervous jitters.

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?

I really need your help! He's driving me crazy! Thanks for your thoughts!

[Yet another guy]

Is he a spineless jerk or an incredibly scared romantic like myself?

Nothing you've said indicates either way. How should we know?

Should I tell him I like him and risk straining everything due to our distance and my forwardness?

If he does likes you, being forward is never a bad thing. Considering your meeting at the bar though, he doesn't seem to see you as more than a friend in my opinion.

[devonbrown]

Who knows how he feels? You have never talked to him.
Sure, you have had conversations about things, but the real conversations are always going on in your head behind your words.

Just ask him out. On a date. Use the word. Take a deep breath and make it clear.

Stop letting fear get in the way of what you want.