awol314

Well, that certainly is an asset that can make the ladies swoon!

CG, I completely understand what you are saying. I'm in a somewhat lonely place myself, having moved to a different part of the country a year ago where I didn't know a soul.
You've expressed your dilemma quite well, and you know where the pitfalls are. If this would be anybody but the friend of you drinking buddy I'd say go for it and just stay aware that you are mostly driven by loneliness. But this combo is an almost guaranteed recipe for disaster, *especially* since you describe yourself as a nice guy (which I have no doubt you are). Nice guys tend to want to do damage control when things go pear shaped and this situation will. You will hurt people (3 to be exact) and you yourself the worst. You'll put yourself into severe danger of drinking again and you'll end up lonely on top of this.
Also, what are the odds that this girlfriend of your buddy will want to support your sobriety? After all, you met in a bar... I don't know. And would she want to stay friends with your on-off drinking partner?

I want to say that what's going through your mind is absolutely normal but just can't produce a tenable situation. Easy for me to say, I know - I deal with being on my own reasonably well and still feel the sting. If you do go ahead and call her you've got to brace yourself for the moment it all implodes, and surviving that would mean for you to be not so nice, which is against your nature. Could you deal with that?