I'd like to restate my point a little.
In trying to convince HH to go for it, I fear that I might have come across as a lecherous perv who is simply looking for a cheapo thrill.
That isn't really what I'm trying to say. It isn't just about getting in her pants and all that. Laugh if you want, but that's not it. I don't even want to know.
I believe that there is no such thing as a perfect life, a perfect relationship or a perfect anything. There are only perfect moments and if say, I was a single man and had such a chance I would consider it a chance, just a chance to live one of those perfect moments and that makes it totally worthwhile. IMO, anyways.
A "perfect moment" can take many different forms and in a case like this it could simply be to beat the fear and enjoy the company of somebody that wanted to date you, despite the stigma of the age gap. Just having a few laughs and a nice conversation or dinner or something would be a victory. Anything more would be a bonus.
Hey, if you crash and burn then you'll get over it. If you don't take the chance I'm not sure you would ever be right with it.