Hugh Hefner's marriage to 31-year-old Crystal Harris might have seemed outside of the traditional model, but the pair appeared immensely happy together.
Catalogued in his extensive social media history are tons of mentions of their fairly mundane activities (like a lot of scrapbooking), considering his reputation as a ladies' man, and her start as a Playmate.
Before tying the knot on New Year's Eve in 2012, the 91-year-old Playboy founder and Harris signed an "ironclad" prenuptial agreement, a source revealed to Us Weekly. As a result, Hefner's estimated US$43 million fortune will be split among his four children, the University of South Carolina film school and multiple charities.
Hefner has always been a charitable man, so the fact that some of his fortune will be donated to various organizations is not a surprise. In fact, his last few tweets before his death were directed at encouraging people to come together to help those affected by Hurricanes Harvey and Irma.
It is surprising, however, that Hefner did not leave an appointed sum to his beloved wife. That's not to say Harris won't inherit any money just because of their prenup, as it is possible that Hefner could have left her something specific in his will.
Additionally, in 2013, Hefner bought his wife a US$5 million mansion because he wanted "to make sure Crystal has a roof over her head when he's gone," TMZ reports. Thus, at the very least, Harris is left with a home.
Harris began dating Hefner when she was 22 years old. The couple was originally set to marry two years later, in 2011, but Harris called it off just days before the wedding due to cold feet. However, they soon reconciled and said "I do" a year later.
"Last time it turned into a big ordeal and then it all fell apart," Harris previously told Us Weekly of her wedding. "This time around is amazing ... I'm very happy and Hef's very happy and we're excited."
While Hefner and Harris have always raised eyebrows due to their 60-year age gap, the two were adamant that they truly love each other.
"I don't notice the age difference with Hef at all," Harris told Entertainment Tonight following their engagement in 2011. "If anything, I have to keep up with him!"
Hefner also publicly acknowledged his age difference with Harris before the two tied the knot. On Twitter, he stated that it "really doesn't matter."
During their five-year marriage, Hefner and Harris shared a number of sweet photos together on social media, illustrating their tight bond.
Just check out their Miley Cyrus and Robin Thicke Halloween costumes from 2013:
And this sweet, silly selfie from 2014:
And here they are celebrating Hefner's 91 birthday back in April:
Harris is Hefner's third wife. The legendary ladies' man was previously married to Millie Williams and model Kimberley Conrad. He also had two children with each of his ex-wives: Christie and David from his first marriage, and Cooper and Marston from his second.
There was a common misconception that I put the kibosh on the partying at the Mansion. It had nothing to do with me.
Hefner has always maintained a good relationship with his exes. In fact, earlier this year, second wife Conrad happily recreated her 1988 Playboy cover.
Conrad also recalled fond times she spent at the Playboy mansion. "There was a common misconception that I put the kibosh on the partying at the Mansion. It had nothing to do with me," she said. "The Playmates still came over."
As touching tributes to Hefner roll in, Hefner's wife has remained silent as she privately mourns her loss. Since the news of his death broke, the 31-year-old has deleted her Instagram account and set her Twitter account to private.
He will be greatly missed by many, including his wife Crystal, my sister Christie and my brothers David and Marston, and all of us at Playboy Enterprises.
However, Hefner's son Cooper, who is Playboy's chief creative officer, released a statement regarding his father. In it, he referenced his stepmother, Harris.
"My father lived an exceptional and impactful life as a media and cultural pioneer and a leading voice behind some of the most significant social and cultural movements of our time in advocating free speech, civil rights and sexual freedom," Cooper said.
"He defined a lifestyle and ethos that lie at the heart of the Playboy brand, one of the most recognizable and enduring in history. He will be greatly missed by many, including his wife Crystal, my sister Christie and my brothers David and Marston, and all of us at Playboy Enterprises."
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