This is the key line. He'd been a standup comedian for 20 years and though he loves it but he's not making it. And I have heard that the majority of popular male comedians actually get a TON of women. Women LOVE funny men and if you are a well-known, well-paid, funny man-- forget about ever settling down!
I am positive he knows it too. So he either remains comfortable where he's at or he has to search for other alternatives :(
But it is terribly sad to have to let your dream go...