Wow, I read the whole thread. I need to follow this story.
We're just people giving advice on a gaming forum, so you don't need to listen to what I say, but I'll give you my two cents.
From reading this thread I'd say you're waaaaaay overthinking things and waiting for the "perfect" occasion. Except the perfect occasion is any time, really. Like Nikkom said, just talk to her, be confident, make some joke and remind her she owes you a coffee (if she remembers at all at this point). You could have done it many times already, I'm sure.
Another thing is, if you ask her for coffee but then don't remind her and let time pass, she's gonna lose any interest she may have had fast, because that makes it seem like you weren't interested enough to actually have that coffee in the first place. Don't wait for the next "event" to make your move, you're just gonna keep delaying this.
If you really have such a hard time asking her out for coffee, here's a plan B. Why don't you invite her to some small party / BBQ / drinks outside or whatever with a small group of your friends? Some event you're organising. That way you'd lose the shyness associated with asking her "on a date" and make it seem a normal event. But, it would show her you like her enough to choose her for this small event and you'd have the chance to talk to her and make her feel confident around you and vice-versa. Have a few drinks and laugh. Then act FAST (you don't want to be friendzoned) and casually ask her if she wants to have some damn drink or coffee with you some other day because you're free and bored or whatever. Then take things from there and come back to this thread :P
No troll is too much for me to handle. I rehabilitate trolls, I train people. I am the Troll Whisperer.
