The Playboy founder died on Wednesday at age 91. Madison became one of his live-in girlfriends at the Playboy Mansion in 2001 and later became his main girlfriend while living with Kendra Wilkinson-Baskett and Bridget Marquardt, with whom she starred on the E! reality show The Girls Next Door. Madison and Hefner broke up in 2008. He wed for the third time in 2012 and ditched his multi-girlfriend lifestyle, while she herself got married a year later and had two kids.
On Thursday, she was photographed out and about her family in Los Angeles. She appeared expressionless while carrying a large beverage. On Friday, she was photographed receiving a Starbucks delivery at a Hollywood home, smiling widely while dressed comfortably in a purple Jack Skellington "Bone Daddy" T-shirt and black Harry Potter "Ravenclaw" sweatpants.