But the Playboy founder says he won't be making that same mistake in the new year, telling People this week that he "dodged a bullet" when Harris dumped him days before their scheduled June wedding.
"I am clearly not meant to be married," the 85-year old said. "Married life isn't for me."
Hugh Hefner on Piers Morgan Tonight
Don't cry for Hef, however. He's far from lonely.
The bachelor refers to his latest girlfriends, Shera Berchard and Anna Berglund, as "special ladies" and told the magazine he'd be "on top of my game" in 2012. It's unclear which of those women he's nicknamed game.