Hugh Hefner was born on April 9, 1926 in Chicago. He served in the U.S. Army for two years during World War II before transforming the adult entertainment industry with his groundbreaking publication Playboy. Now, the 86-year-old sophisticate has announcement his engagement to Crystal Harris, 26 -- the same woman he was engaged to in 2011. (She called it quits five days before the wedding.) At the time, Hefner said he didn't rule out having more children (he already has four from previous relationships).
Hefner's oldest child, Christie, was born in 1952 -- about 34 years before Harris. Born in 1986, the model was Playmate Of The Month in 2009. When asked about the age difference, she has said that, if anything, "I have to keep up with him."
But, as with Demi Moore and her new younger boyfriend -- she's 50 and he's 26 -- what could Hefner and Harris possibly have to talk about?
After all, Hefner grew up during the Great Depression. Harris probably hasn't even seen "The Waltons."
For a list of 12 subjects the two couldn't possibly discuss, check out our slideshow. And feel free to add your own suggestions in comments.