I am old, and I lost 130 pounds a few years ago. Maybe my hardest adjustment was losing the self-deprecating, fat part of my personality. How did I overcome this? Brutal honestly, accepting the good, and ignoring the bad. Not just in my life but in others.
I have asked several girls if I were too old for them. About half say something positive about how they'd love to spend time with me??? Some say yes, and smile. Some say no. It is very strange, but after a lifetime of the other stuff, I am well pleased to accepted.
The point is, it is a legitimate question. If a guy directly asks, answer honestly. BUT...if a guy uses it as a talking point or a point of argument, then drop it fast. He has other issues. Just my opinion. And it is a great article you have written here.