An Awkward Question

Yet again I'm having trouble sleeping. Here is what's on my mind this time:

There is this guy I used to work with who we'll leave nameless here. He is a pretty awesome guy that I've known for a year or two. We usually had fun together on the job. We tapped into each other's goofiness, sexual innuendo passed between us constantly (more so than it did between me and almost anyone else...it's kinda my schtick), etc. Some people that worked with us thought he may be gay (someone actually asked him outright in front of several other coworkers, at which I was initially stunned, then walked away trying unsuccessfully not to laugh hysterically). For the most part, I didn't think about it because I didn't care for most of the time we worked together.

I have quite a bit of free time on my hands, more so than any person should. As a result of this, my mind tends to wander wildly. One of the things that I have pondered - given the apparent question as to this guy's sexuality combined with my nagging solitude - was this: had he actually been attracted to men in general, was he attracted to me and would a relationship between us work? As to the relationship question, probably not because this would mean he was in the closet. All of the anecdotal evidence points to relationships where one person is in and the other is out being very strained because of divergent interests. There are also some other reasons it may not have worked in the long-run, but we need not go there. Even given that, I have taken the position that if the opportunity arose, I'd just go for it. Better to try and fail than not try and wonder "what if" in situations like this.

This whole thing has nagged me sporadically over the past several months. I think were I to see him face to face again (which seems unlikely at this point and this doesn't really seem like an internet/texting question) I would be hard-pressed to resist asking a very awkward question: did we ever have a shot (and I'd have to emphasis an honest and confidential answer...I'm great with secrets)? If we did, then it's out there and at least we both are on the same page. If we didn't and it's all in my head (which seems BY FAR the more likely scenario), I'm 100% okay with that. No harm, no foul...at least on my part. Either way, I feel the need for an honest answer to put my mind at rest.

Men...why do they always do this to me? Bastards...