My impression from a few Club Randoms was that his high school girl did a number on him. Likely turned him off to marriage & long term commitment after that.

I would imagine at some point being around Hollywood and Playboy got him his popular/in crowd experience. Likely found he didn't really like it in the end.

His career being busy and on the road also cemented his lifestyle. On the post side of that perhaps he wonders as he ages, (which one must listen for the minor context clues) if he missed out on some who was not either the heartbreaker or the Playboy pin up.

Someone to love him for who he is, which is what most people hope for. This is of course buried deep within and never shown with the wealthy bachelor facade. As former bachelor's like Clooney, McConaughey, and others eventually found non industry quiet beautiful, successful, bright women.

Just a contrarian perspective on the high school/popular story, that he will likely never voice. Only he knows if it is there.