Cynthia and Hef pose for a newspaper ad sponsored by the Hat Institute of America.

Hef's preeminent romantic relationship of the early Sixties, however, was with blonde Cynthia Maddox, a Playboy receptionist and secretary who became his trusted Assistant Cartoon Editor. "I was crazy about Cynthia," Hef admits, noting that they shared consuming interests in art and classic movies. And, says Cynthia, "We absolutely agreed on cartoons." What they didn't agree on was marriage, and when it appeared that it wasn't in the cards, Cynthia left.

Hef with Cynthia at Playboy's Ninth Anniversary Christmas party, December 1962