My problem is of the "should I ask this guy out or not?" variety.

So, background. I have never dated, and I have never asked anyone out, which has started to bother me lately. (I do realize it might be partially wanting to fit in, my recent friends have more expansive dating histories or are at least dating atm than the ones I've had longer, but this is not the actual point).

One time when I was complaining about my lack of dating history to friends in IRC, one of them what I thought about one of the guys in my gaming circles (PFS, so it's not a regular group with him). She said that she thought he might be interested in me. My response was mostly "I wouldn't mind that". This happened in December. Since then I've mostly just tried to find out more about the guy, mostly by talking with him on IRC (not one on one, just picking up conversations when he says something). Thus far no red flags have popped up, and I've been trying to gather the nerves to ask him out.

However, the friend who initiated this doesn't know the guy that well, and told me that I shouldn't take her words as the absolute truth. Also a couple of other friends, when we were joking about who I should date, and thinking of non-taken guys we know, told me that they wouldn't recommend him. They didn't specify, and I didn't push, because I didn't want them to know I might be interested. They do know him better than the first friend, however.

So, opinions. Should I do something about this? We're both on the majorly shy side, so waiting for him to do something propably won't work. There are two problems, I'd say. First, is he even interested. Second, even if he were, is it worth the try. I personally haven't noticed things that would make into an instant "no". I just keep thinking about "is there actually anything to lose if I ask" and "man up and ask already, at least then you'll know if there's even any reason to be nervous about all this".