I don't think it takes a lot of confidence. He's not a you or I...regular Joe's. He's a professional QB in NYC. Women throw themselves at him.
We had a guy on my college team that was a virgin, not good looking and had no clue how to talk to women...never had a GF.
We went out drinking one night and told woman in the bar that we were celebrating as a group because our good man Danny was just drafted by the Pirates and got a $7 million dollar signing bonus. He had girls all over him the entire night. They were like ants with dropped candy on the ground.
I used to hangout in areas where Braves players used to frequent....these guys just sit down and girls come to them.