Spot on.

For 2+ decades I’ve watched and learned what makes a woman attracted to a man.

I’ve seen guys with no money, no jobs, no physiques - attract the most beautiful women.

I’ve seen guys like your friend - 10’s on paper - fall flat on their faces over and over.

And so many people attract a person they don’t really want — and repel the person they really want.

There’s a dynamic process to all of it.

In your friend’s case — yes he will need to start again. He will need to unlearn so much that made him “successful”. That gets more challenging as people age. But it can be done.