This guy knows his stuff.
Here's what he had to say in an interview with Rick Reilly of Sports Illustrated:

"You can't let them know you're that interested. I try to get this across to my best friend. He's really into this girl, but I keep telling him she's got to leave that date thinking, 'What's wrong with me?' "

Ouch. Tom Brady may be able to get away with cultivating low self-esteem in women because he's loaded and good-lookin' and has a Super Bowl ring [OK, you're right - three rings - Ed. note], but attention ordinary men - do not try this at home.

The Rick Reilly piece is also fascinating because Reilly manages to pump up Brady's ego to tremendous proportions, describing him as a sex god of the ages: "See, Brady is Namath with a milk mustache. Mothers want him for supper and daughters for everything after."

Eww. The thought of Brady moving from cougar to kitten, spreading his seed everywhere, and then giving guys dating advice is terrifying.

Since Brady has been put in the position of giving advice (SI approached him, not the other way around), then we'll give him a little - just shut your yap and play ball. You're good at that. Quite good, actually. Go with your strengths. You are obviously not so hot at dating (Exhibit A: Babydaddygate).

http://bostonist.com/2007/09/13/mr_lonelyhearts.php