Actually I don’t see anything wrong in this.I think your greatest concern is the age difference,not that he is your boss.
In the company that I work in,the CEO got married with the Sales Director and my supervisor married a sales representative.
My CEO’s wife even moved from Brazil to Germany,where he was located…so there’s nothing strange about this.
Maybe he is feeling old and jokes about this stuff which concerns you to see what impression he has about himself.
I mean if you both like each other’s company and none of you has any commitments you should go for it. At least give it a try,so that you are not sorry later that you missed this…Anyway I wish you both good luck

he your boss and can lose his job for dating a employee, the age thing if your over 18 y.o and his wife dont mind that not a issue

I dont see a problem. Honestly, as long as no one is taking advantage of the other, then whats the problem? People will say that absolutely no matter what this relationship will be unequal and he will have more power, well I married a man 20 years older than me who was once a professor of mine, let me tell you, theres no inequality here. Once he gets a new job, go right for it… but wait for the new job to avoid any messes that could otherwise occur.

well, if you love him and your over 18 then go for it!! But if your under 18 (0r maybe 21) then you should wait for that love to burst (or if you want, have it in private places!!)

hope this helped!!