The Life of Barbi Benton: Hugh Hefner’s One That Got Away

Their First Date Was at an LA Disco

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On the edge of the ’70s, it makes sense that Benton’s first date with Hef was at a disco. She admitted that Hef asked her out again and again, but she already had her choice of three suitors: her college boyfriend, Golden Globe-nominated actor Jimmy Caan, and the Playboy mogul.

Benton only agreed to go to the disco because it was a group date that included famed author Shel Silverstein. She was a major fan of his work. Hef ended up winning her heart, however, and they began a whirlwind romance packed with celebrity appearances and Hollywood excess.