Still, she remained in a relationship with Hefner until 2008, when she moved out of the Mansion and on to new opportunities. Hugh Hefner reportedly banned Holly Madison from wearing red lipstick .

2002: Madison reveals she'd love to marry Hefner The model, who quickly became Hef's "No. 1 Girl," made it clear from the beginning that her heart only belonged to Hefner.

Holly Madison was just 21 years old when she moved into the Playboy Mansion back in August 2001, and she is thought to have started dating Hugh Hefner that same year — when he was 75.

After splitting from Hefner, Madison began dating Electric Daisy Carnival founder Pasquale Rotella in 2011. They tied the knot in Disneyland on Sept. 10, 2013, but got divorced in February 2019.

Playboy founder Hugh Hefner released a statement Monday saying former girlfriend Holly Madison’s new book is her attempt to “rewrite history in an attempt to stay in the spotlight.” In an ...

Hugh Hefner is not amused that his ex-girlfriend Holly Madison is releasing a tell-all book about her time in the Playboy Mansion. The retired Playmate and reality television star writes about ...

Holly Madison is reflecting on her past romance with the late Hugh Hefner. The Girls Next Door star, who dated the Playboy magazine founder between 2001 and 2008, recently opened up about the ...

Hugh Hefner is down a girlfriend. Hefner and Holly Madison, one of E!’s “The Girls Next Door,” are no longer dating. Hefner said he’s been “down in the dumps” about the split.

UPDATE: Holly is now openly admitting that she is “in love” with Angel. Relationship now doomed. Early last month, Holly Madison revealed through her MySpace page that she was in the process of moving ...

NEW YORK (AP) -- Holly Madison doesn't like talking about living at the Playboy mansion and dating Hugh Hefner, but believes "it's important to tell the truth of my story." The 35-year-old former ...

Holly Madison can look back now and see that her relationship with late Playboy publisher Hugh Hefner, whom she dated from 2001 to 2008, wasn't good for her. But, when their breakup was happening ...