If I was worth a billion dollars, I'd like to think I'd be able to get better looking chicks than the ones he's apparently gotten with, especially considering he allegedly "paid for companionship".
Listening to Toucher & Rich way back when this started, Fred nailed the situation on the head (no pun intended): Tiger Woods is a giant nerd that doesn't know how to act around women. So much so, that he had to have his friend ask Elin out on a date for him.
Being worth $1B, he should be depositing more confidence in the toilet than most men will ever have.
If this D-bag can pick up models at bars

Tiger Woods should be ashamed of some of what he's slept with.