Perhaps you should just take the cheerleader route. He is happy and you should be. I think he would feel bad if, he knew you weren't happy. His career and achievements is one thing but, personal happiness is another. In the interviews I have seen he has never been malicious or puts others down . He may have been frustrated or grumpy at times but, he always has good words for others and I guarantee he would have the same words for you and that is to enjoy the career but, life is good to live. Remember Moira you have a second chance don't go backwards. Take inspiration from him since, you have followed him for decades and see how he has progressed.
He is a risk taker no doubt about it. He met someone and fell in love and worked it out. I know there had to be obstacles but, he made it happen. In other words he took a leap of faith and now it looks as though he has won. Its easy to say what you are not . It takes gusto to say what you are and going for it . Life is too precious to wilt away. I am right behind you !!