I was married when I went sly and still married to the same great women so it is not easy for me to offer advice.  At first they may be scared of you or think you are associated with some group or gang.  Do not get discouraged and do not shy away from your slyness.  As mentioned before, confidence is it. 

I was waiting on Champ to weigh in on this one.   

My luck has stayed the same....hair or no hair....my wife makes sure of it.....

I still haven't given it a try. The last time I went out to a bar or something of the sort I was sporting the MPB bigtime... and it was all I could think about. On more than one occasion a gorgeous woman would sit next to me at the bar, but all I would think about was how they wouldn't be interested in me because of what was on my head.

I kinda fear getting overconfident and doing something I regret, though... I tend to function on extremes and after a long time of little confidence I may spring back into an impulsive madman. It'd probably be fun, though 

As many others have said, confidence is the key bro, carry yourself with good posture put a smile on your face because your far more lucky than you realize, and feel good about yourself. You can take the most "beautiful woman on the planet, give her bad posture a sad look on her face, and she's nothing, take an average girl and give her the things i just told you about, and there instantly more attractive. Personality/good sense of humor always helps too.