Hugh Hefner's Many Exes

Sandy and Mandy Bentley
After Hefner’s second marriage ended in 1998, he was “beat up emotionally and bruised,” he later told The Daily Beast, and sought comfort in numbers. Two of the women he started seeing were Illinois-born twin sisters Mandy and Sandy Bentley, who quickly became residents of the Playboy Mansion and were featured on the cover of the lad mag in May 2000. However, Sandy reportedly didn’t want to be tied down to one person ... more 

Sandy and Mandy Bentley
After Hefner’s second marriage ended in 1998, he was “beat up emotionally and bruised,” he later told The Daily Beast, and sought comfort in numbers. Two of the women he started seeing were Illinois-born twin sisters Mandy and Sandy Bentley, who quickly became residents of the Playboy Mansion and were featured on the cover of the lad mag in May 2000. However, Sandy reportedly didn’t want to be tied down to one person either, and when Hefner found out she was seeing someone behind his back, he showed her the door. less