So I found myself within great company Saturday night at this club in downtown Orlando called Cuba Libre. I had an awesome time and by the name as you can guess its a spanish club but that's neither here nor there. The topic at hand is what happened towards the end of the night. Me and my boys as well as the ladies we went with were downstairs enjoying this Aventura set and all of a sudden, like a fairy tale, THEE mostbeautifulestgirlintheworld walked in front of me with two of her friends and were a couple feet away from me. I was instantly mesmerized and I seriously couldn't stop staring over at her. Dark skin, silky black hair just past her shoulders, full pouty lips, light colored eyes (could have been fake but whatever), a tattoo on her shoulder (I love tattoos and piercings) and she was killin' the black dress she was in. Didn't peep the shoes tho but I digress. So I tapped my boy's shoulder and got his second opinion cause that's what men do and he approved. I mustered up enough courage finally to step to her but her and her crew walked away. Mission failed...until a few minutes later as the night was about to end and there she was again. Here's my chance.
Now, every man can agree w/ me on this and its when we see a woman who catches our eye as well as interest we observe her and how she acts before we make our move. Like a lion to a gazelle. And that's what I did and the more I observed the more interested I became. After I gathered enough information based off her mannerisms I found myself more intrigued. So I walk up to her, with absolutely no game plan. Probably my first mistake so I said the first thing that popped in my head and it went like this:
Me: *lightly taps back* Excuse me.
Her: *looks up* Yes?
Me: I'm sorry, but I just had to come over and tell you I think you're absolutely beautiful.
Her: *hand over mouth* oh wow, thank you so much that was sweet! What's your name? *holds out hand*
Me: Chauncey (she finally got it after three tries btw)
Her: Oh! That's a nice name, well I'm Autumn.
Now, at this point one would think "ok boom, I got this she def seems interested" but not so much the case here. Wanna know what I did? I simply said "well it was nice to meet you," she said likewise and I walked.away. Yes. That's right. Me. Usually its the other way around and an uninterested woman just walks away or uses a scapegoat. So, why I did that I honestly couldn't tell you except for the simple fact I punked out and committed a Holla Fail. I don't Holla Fail, I just don't. But apparently my 3 month hiatus from conversing with the opposite sex played a part into me Holla Failing. This was the first woman I've been remotely interested in months and I dropped the ball on some Braylon Edwards shit. Now to give some background information it was just about closing time and the club was clearing out, my group was about to leave themselves, and I felt the burning watching eyes of my brothers seeing if I'd come back as a winner or a loser. The pressure got to me and I just simply wanted to end it because outside of her being attractive and her name its all I had. The infamous Mad TV sketch of "Can I Have Yo Numba" popped in my head and that was the deal breaker for me and I had to retreat. It just seemed to quick, too thirsty to just simply ask for her number like that. I'm banking on probably never seeing this woman again because I just don't go out as much as I used to and who's to say she does as well? So I'm chalking it up as a loss.
Now I know I'm not the only man to have done this so I ask what do you think I SHOULD have done? Because to be completely honest my dating patterns revolved around meeting friends of friends of friends if you catch my drift. So no woman has necessarily been a complete stranger to me and conversation was easy to come by plus I had time. So help us men out ladies and keep it real: we both know YOU want the man to approach you so offer some advice, what could I have done differently with the short amount of time I was given? What are some things you like for a complete but mildly attractive stranger to say to you in order to break the ice? Lastly the most important question is "when" is a good time to ask for the digits and close the deal so to speak?
Men: Share some of your success stories and failures if you're brave enough to do so.