I’ve never known a girlfriend who enjoyed me making jokes about marrying her, making pretend offers to marry her. They never laughed. They never found it funny.
As soon as you can laugh about something, it means it’s not a big deal. As soon as a society starts making jokes about adultery, it means that adultery is not such a big deal.
Jewish humor didn’t develop until the Enlightenment and it chiefly developed among secular Jews. Orthodox Jews who are funny do it, I think, out of an internalization of our society’s secular-religious split (that there is a place for religion and a place to keep religion out such as the public square). The more religious the Jew, in my experience, the least likely he is to be funny. The funniest Jews are overwhelmingly the most secular. They are the most fearless. They don’t have whole swathes of life that are off-limits to humor because of holiness concerns.
I think the Talmud says something about everyone knows what happens on a wedding night between the newly married couple, but anyone who makes jokes about it does not go to the world to come.
I think the more secular I am, the funnier my writing is. The more religious I am, the less funny. It is much harder for me to make jokes about Judaism when I’m taking it most seriously.