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For those who missed the other thread, the girl he's currently dating is an 'I don't know what I want, so I'll keep us in the between friendship-relationship limbo' sort of girl. The advise over there seems to be to move on and my understanding is that they're not exactly a couple, as such.
I say go for it. I had a phase in my younger days (as did everyone) where the thought of asking someone out on a date seemed paralyzing until I realized that it's really not that big a deal to either party. You're not giving her an engagement ring or anything, just looking to see if there's a possibility for something more than friends. Think of it in the reverse; if a female friend you didn't have an interest in were to ask you, you'd likely be flattered (I know I was on the occasions it happened to me). It's really much scarier to you than it is for her and odds are she already knows anyway. We aren't as good at hiding these things as we think we are and that goes for the girls as well as the guys.
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