PICTURED: Melancholy Holly Madison, 37, spotted for the first time since the death of her ex-boyfriend Hugh Hefner at 91

By Ross Mcdonagh For Dailymail.com

Published: 21:54 EDT, 28 September 2017 | Updated: 12:11 EDT, 29 September 2017

She was Hugh Hefner's number one girl for the longest time. 

And his death seemed to be hitting Holly Madison hard as she was spotted for the first time on Thursday since the sad news broke.

The 37-year-old former Playmate cut a melancholy figure as she stepped out with her family in Los Angeles.

Mourning: Melancholy Holly Madison, 37, was spotted for the first time on Thursday since the death of her ex-boyfriend Hugh Hefner at 91

Mourning: Melancholy Holly Madison, 37, was spotted for the first time on Thursday since the death of her ex-boyfriend Hugh Hefner at 91

Hef's ex fittingly wore all black, including a demure floral-patterned dress and a Louis Vuitton purse.

Carrying a drink, a snack and her phone, she left her home with her four-year-old daughter Rainbow and one-year-old son Forest.

The reality star moved into the Playboy Mansion in 2001, aged 21, and was girlfriend to the publishing magnate for seven years.

During that time she became one of the stars of Girls Next Door, a reality show revolving around her and Hef's other two live-in girlfriends,  Bridget Marquardt and Kendra Wilkinson.

Sad: The 37-year-old former Playmate cut a melancholy figure as she stepped out with her family in Los Angeles

Sad: The 37-year-old former Playmate cut a melancholy figure as she stepped out with her family in Los Angeles

Dark day: Hef's ex fittingly wore all black, including a demure floral-patterned dress and a Louis Vuitton purse

Dark day: Hef's ex fittingly wore all black, including a demure floral-patterned dress and a Louis Vuitton purse

Holly was considered his 'main girlfriend', and openly stated she wanted to marry him and have children.

However the twice married Hef didn't fancy a third trip down the aisle, and they eventually broke up in 2008. 

Things soured between the two when Holly blasted her in ex in her her 2015 memoir, Down The Rabbit Hole.

Mom-of-two: She left her home with her four-year-old daughter Rainbow and one-year-old son Forest

Mom-of-two: She left her home with her four-year-old daughter Rainbow and one-year-old son Forest

The one that got away: The reality star moved into the Playboy Mansion in 2001, aged 21, and was girlfriend to the publishing magnate for seven years

The one that got away: The reality star moved into the Playboy Mansion in 2001, aged 21, and was girlfriend to the publishing magnate for seven years

She described her life their as a 'living hell', branding her ex pathetic, predatory, emotionally manipulative, and a disappointing lover. 

She even said life in the Mansion became so depressing that she even contemplated suicide. 

 In the book she details first meeting him in 2000, when after a night out clubbing with his 'girlfriends', she realized that she was expected to sleep with him.

Three's a crwd: During that time she became one of the stars of Girls Next Door, a reality show revolving around her and Hef's other two live-in girlfriends, Bridget Marquardt and Kendra Wilkinson

Three's a crwd: During that time she became one of the stars of Girls Next Door, a reality show revolving around her and Hef's other two live-in girlfriends, Bridget Marquardt and Kendra Wilkinson

She claimed her first encounter with Hefner was him offering her a Quaalude from a tissue in his pocket.

'Usually I don't approve of drugs, but you know, in the '70s they used to call these pills ''thigh openers'',' she claims Hefner told her. 

Afterwards, Hefner accused her of 'rewriting history in an attempt to stay in the spotlight.' 

Hef went on to marry 31-year-old Crystal Harris, while Holly married the father of her children, businessman Pasquale Rotella. 

Bitter: Things soured between the two when Holly but her ex on blast in her 2015 memoir Down The Rabbit Hole

Bitter: Things soured between the two when Holly but her ex on blast in her 2015 memoir Down The Rabbit Hole


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