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The Loves Of Hugh Hefner

Gettyimages | Dan Tuffs
By Carol Cassada

It's been over two years since the death of Playboy founder Hugh Hefner.

The magazine mogul is considered an icon thanks to the launch of his magazine Playboy.

Much like the name of his magazine, Hefner was known to have a playboy lifestyle.

He was known to have parties at The Playbody Mansion with some of the magazine's Playmates and other celebrities.

While Hefner often lived the life of a carefree playboy, he was also a husband and family man.

So let's take a look at the personal life of the legendary Hugh Hefner.

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Mildred Hefner


Hefner married his first wife Mildred Williams in 1949.

However, before their wedding, Mildred stunned Hef when she admitted to having an affair while he was serving in the army.

Hefner was devastated by the revelation, but found it in his heart to forgive Mildred and they continued with their wedding.

The couple's first child, a daughter named Christie was born in 1952. Their son David was born three years later in 1955.

Hef and Mildred divorced in 1959, but the two remained good friends. Hefner even reportedly brought Mildred a house when she was facing financial trouble.

Barbi Benton

Gettyimages | Images Press

Following his divorce, Hefner would enjoy the single life.

He dated a string of Playboy models throughout the years, but one girl who caught his eye and his heart was Barbi Benton.

Benton was just 18 years-old when she began dating Hefner in 1969. He was 42 at the time of their relationship, 24 years her senior.

The couple met on the set of the show Playboy After Dark, where Barbi would serve as co-host with Hef.

Benton's career in acting and music took off as her relationship with Hef continued.

The couple even moved into the Playboy Mansion, which Benton convinced Hefner to buy.

After seven years together, the couple split up in 1976. Benton cited infidelity and Hefner's lifestyle as the reasons for their split.

Kimberley Conrad

Gettyimages | Jim Smeal

A health crisis forced Hefner to change his ways.

After suffering a stroke in 1985, he decided to give up on his carefree, partying lifestyle.

In July 1989, he decided he was ready to settle down again. He married Playboy model Kimberley Conrad, who was 36 years younger than her husband.

Less than a year after their wedding, their first son Marston was born. Their second son Cooper was born over a year later in September 1991.

With two young children in the house, Kimberley put an end to the wild parties that used to occur at the mansion.

Hugh and Kimberley separated in 1998, and he brought her a house close to the mansion so he be near his sons.

In 2009, after nearly 11 years after their separation, Hefner finally filed for divorce.

Holly Madison

Gettyimages | Steve Granitz

After his separation from Kimberley, Hugh began dating a few Playboy models.

At one time, he had seven girlfriends. But before long, it was shortened to three.

Holly Madison, Bridget Marquardt, and Kendra Wilkinson were Hefner's main girlfriends.

Even though Hefner loved all of the girls, Holly was his main woman. While Holly made it clear she wanted to marry Hef, he seemed against the idea of marriage.

In 2005, the girls signed on for the E! reality show The Girls Next Door, which depicted their lifestyle at the mansion and their relationship with Hef.

In 2008, Hugh and Holly broke up. Shortly afterards Bridget and Kendra would move out of the mansion.

Crystal Harris

Gettyimages | Charley Gallay

In 2010, Hefner was ready to settle down for the third time.

He became engaged to Playboy Playmate Crystal Harris, who was 60 years younger than him.

They were scheduled to be married on June 19, 2011. But five days before the ceremony, Crystal changed her mind and ran off.

Despite the devastation of her running off, Hefner forgave Crystal and they got back together.

They got married in December 2012 and stayed together until Hefner's death on September 27, 2017.

Since Hefner's death, Crystal has been trying to move on with her life and find her own identity.

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