In a way, we're friends and colleagues forever. You see, the industry we're going into is a small world, and the people I know now, I will know for life. So what I'm afraid of is, if asking him out out can skew a potential friendship/working relationship, I'd rather be permanent colleagues/friends. That's why I try to be at least more than 50% sure first before trying.

Thanks for the replies guys! Whatever I end up doing, you were all helpful.