When you've been to the end zone as many times as that guy has it probably doesn't even phase him in the least.
And why do you make that assumption? All his girlfriends have been "mother figures", his mom was or still is his manager. Cameron Diaz wore the pants and was adamant about that. And so did the most recent woman...
You have to understand that his persona is purely image driven---when he does interviews you see a less than confident man---eye contact, the way he holds his head, all these are key points.
People always assume that just because a dude is famous that he is smashing chicks right and left...MJ had a playboy playmate in his Thriller video, yet he perferred the company of Emmanuelle Lewis. Women loved themselves some George Michael---but he loved himself some men...