Bold Move or Foolish Move?

With my confidence and swag sagging big-time; I basically have let myself have three options:
a) To hell with even tryin to talk to chicks right now
b) Go from being my passive self and get agressive right off the bat
c) Have my boys do the pursuing for me and then work my magic from there. Well ok, it seems more like Magic's Biggest Secrets: Finally Revealed but you get the idea.

Lets see what I get with choice A:
Strengths- My ego doesn't take any hits and I can't get let down as usual and fail. Sure "you miss 100% of the shots you don't take" but if you're still missing shots that you're attempting then why bother?
Weakness- It just sounds gay. Also, I would be depriving myself.

With choice B:
Strengths- Apparently girls like dudes who are more forward and are willing to take charge. I tend to do this a lot more when I'm not sober as well and it usually works (whether with gettin digits or hookin up, shit like that).
Weakness- If I go this route and do get rejected, I do not take it well whatsoever and it destroys my night

With choice C:
Strengths- It's like gettin a reference and you don't have to prove your worth as much in order to succeed.
Weakness- If you don't impress her then you have no game. Maybe it wasn't your night/her type either but you're gonna think you have no game. Which in turn, burns your ego even more because you had a shot at the title and lost.

So last Friday night, I went with choice B. I went to this bar on the Upper West Side in whom my boy knows a whole lot of ppl (namely for this sake of the conversation chicks). I decide on some super-random shit to talk to this one bartender who has worked there and I have met exactly one time, a chick named Andrea. I thought she was lookin pretty damn good...so I said fuck it why not and conversed with her for maybe 20 minutes. Then for some odd reason...I asked her if she had time and wanted to go ice skatin with me at some point (ehh next week or so). After jokin around about it and her talkin about how she's dated hockey players blah blah blah you gotta impress me- my answer was: I'm flattered; but I'm busy...and I don't think it'd be the right kind of date to go on.

FUCK!

I get dead quiet and on the low I was about pissed off for 45 minutes. I don't know why. I should have expected it though.

Bold move to go for the kill so quickly (keepin it real)? Or foolish move in that I didn't even wait til I even got to know her better (using the date as a ploy for that)?

And so on. Sponsored by my main man Stephon Marbury.