My first wife was almost 30 years older than me, we lasted for 6 years.
That's up to you. Hugh Hefner comes to mind, but maybe not a great example.
Of course you can date him.
i say he is the clear winner in that sitch
yes there is nothing wrong with that it's just a little weird.
It depends on the 25 year old and the 40 year old. Jerry Seinfeld and Paul Simon seem like two success stories.
Sure. My first wife was about 15 years older than I. My current one is 13 years younger.