I originally wrote a different Hugh Hefner gag to go with this image. I thought it was going to be hilarious if some sweet young thing decided that she was too old to date Hef.

I’ll admit that my inspiration was an old joke that I heard about Hefner. I first heard it several decades ago when Hef was in his 50s.

In the joke, Hefner asks a beautiful, 18-year-old girl out on a date. The girl responds, “But, Mr. Hefner, I’ve never gone out with anyone over 20.”

Hef replies, “Me either. ”
Alas, real life is more complicated—and absurd.

After I wrote my Last Kiss gag, I went online and discovered that in December Hefner got married. To a 26-year-old woman.

So I quickly rewrote the gag. Maybe not as quickly as Hef used to “date” young women. But quickly!