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.

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 .

J. Merritt/FilmMagic Hugh Hefner and Holly Madison during Animal Fair's 6th Annual "Paws for Style" Pet Fashion Show and Gala Charity Auction in Beverly Hills, California.

Although she is not currently pregnant, Holly Madison, 28, wants to have Hugh Hefner’s baby in the next two years — and The couple is banking sperm in case Hugh’s age catches up with him.

Crystal Hefner is just some bunny that Holly Madison used to know. The “Holly’s World” star, 44, has blasted the widow of late Playboy founder Hugh Hefner, 37, for seemingly ripping off her ...

Hugh Hefner Slams Former Girlfriend Holly Madison For 'Rewriting History' in Memoir There are only a couple of problems with that, the lawsuit contends: Madison was never interviewed by Dr. Oz on ...

Exclusive Details Ex-Playmate Holly Madison Details First Sexual Experience With Hugh Hefner, Claims It Left Her 'Horrified' Source: mega Shafiq Najib Dec. 15 2021, Published 7:15 p.m. ET ...

Holly and Crystal Harris have feuded, and "it would be a little strange if she was there," says Hefner Mark Gray is a journalist of over two decades. He has written about entertainment, sports and ...

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 ...

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.

Holly Madison - the one-time number one girlfriend of Hugh Hefner - is divorcing her husband after just four years of marriage. The reality star, who appeared alongside the late magazine magnate ...

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 ...