I have a friend that is in much the same mold, other than the football part. Overweight dude his whole life, crushes on totally unobtainable hot girls, and ignores any overtures from chicks that are more in his league. We were talking at the bar one night about a girl that had made it plainly apparent that she was interested in him and he says, "I don't know, I'm just not attracted to her." I respond, "Who the fuck are you to go around turning down pussy?"
He was big into cars, at one time he bought a BMW 5 series on the theory that it would attract women to him. It didn't. In his mid-40s, he owned a Lexus sedan for his daily driver and an absolutely cherry Porsche Carrera. He goes out to Vegas with a couple of our other friends, comes back and is recounting the Vegas trip to me. The highlight of the trip for him was paying 2 grand to drive a Dodge Viper a few laps around the Vegas Motor Speedway. I'm like you paid 2 grand to drive a car when that would have covered an A level call girl? Dude, you own 2 cars and have zero pussy.