Takes his chick to a sports bar to watch NFL football and drink beers.
While you may think Richard is wearing that jersey just to be "one of the guys" and to support his local team, the real reason is far more sinister. Check the shoulder. The "Arm" area if you will. Richard is actually wearing the jersey as a coded invite for the *real* love of his life to come visit him some time and to give him one in the pooper.
This man has hundred of millions of dollars and he's wearing what are those, MacGregor sneakers? Not that he needs to be wearing sneakers made of gold, but something nice that would actually support his clown feet.