Quote Originally Posted by dehro View Post
C is easy (to deal with, that is)
Both B and A deserve better than B being "kept waiting to see how things pan out with A" and A having you not being all that committed with her to begin with, or you wouldn't even be considering B as a viable alternative.

in other words, are you really taken by A or are you just bored with the current situation and want to try something different?
having options is a wonderful thing and one that I quite envy you. try not to misuse it though, and try to take their feelings and your decisions' impact on them into consideration too.
No need to envy me, it was entirely hypothetical. I envy the hypothetical me too, in fact!

Quote Originally Posted by Mary Leathert View Post
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".
Having gone through the "do I or don't I ask" thing (with someone who was giving more direct signs than you've mentioned, no less): ask. Sitting with the question is only going to cause anxiety. Once you've asked, there's 2 options:
1) he says yes. Proceed with s
2) he says no. Proceed with and transition to (hopefully quickly), but at least you'll know you have to move on, and you won't be dealing with the whole thing (being confused and making yourself anxious, if that wasn't clear)