Hugh Hefner and Crystal Harris, 60-Year Age Difference

Sugar Daddy Hugh Hefner with Crystal Harris

When it comes to sugar dad­dies, no one does it bet­ter than Hugh Hefner, founder of Play­boy Enter­prises, Inc. and pub­lisher of the iconic men’s mag­a­zine Play­boy.

Hefner started his career in pub­lish­ing work­ing as a copy­writer for the men’s mag­a­zine Esquire. After quit­ting his job, mort­gag­ing his fur­ni­ture, tak­ing out a loan from the bank, and gath­er­ing money from investors (includ­ing his mother), Hefner launched the first issue of Play­boy in 1953—it fea­tured Mar­i­lyn Mon­roe and man­aged to sell over 50,000 copies.

As soon as the first issue was pub­lished, Play­boy became a point of controversy—not just because of the nude women on its pages, but because of its push for more lib­eral drug laws. But despite the back­lash, Hefner’s busi­ness ven­ture thrived, with issues of Play­boy sell­ing out in a mat­ter of weeks. The 1972 edi­tion, which remains the best-selling issue to date, sold over seven mil­lion copies.

Play­boy Enter­prises, Inc., which was ini­tially devel­oped just as a means to pub­lish the mag­a­zine, even­tu­ally expanded into a tele­vi­sion chan­nel, 12 dig­i­tal net­works, var­i­ous web sites, a radio sta­tion, night clubs, and a licens­ing divi­sion. As the face of Play­boy, Hefner became a leader in business—he also solid­i­fied his rep­u­ta­tion as a sugar daddy extraordinaire.

Hefner’s first mar­riage arguably had a hand to play in his promis­cu­ity later in life. His first wife admit­ted to hav­ing an affair. In order to ease the guilt and hope­fully save the mar­riage, she report­edly allowed him to sleep around. Their mar­riage offi­cially ended in 1959. By that time, Play­boy Enter­prises had taken off and Hefner recre­ated him­self as a new man. He admit­ted to dat­ing most of his Play­boy mod­els, most of them being decades younger than him.

In 1989, at the age of 59, Hefner mar­ried his 27-year-old sugar baby, Play­mate of the Year Kim­ber­ley Con­rad. They had two chil­dren together and even­tu­ally sep­a­rated, with Con­rad mov­ing out of the Play­boy Man­sion and into a house next door.

In true sugar daddy style, Hefner cel­e­brated the split by fill­ing the man­sion with a bevy of young women—he even admit­tedly dated up to seven of them at the same time. But that sugar daddy dream came to an end in 2008, when they all decided to move out of the man­sion. That’s when Hefner, now 82, began dat­ing 22-year-old Crys­tal Har­ris, as well as a pair of 20-year-old twin models.

Two years later, his rela­tion­ship with the twins ended, but his rela­tion­ship with Har­ris per­sisted. In March 2010, Hefner finally had his divorce from Con­rad final­ized (they were sep­a­rated, but stayed legally mar­ried for the sake of their kids), and a few months later, he pro­posed to his sugar baby. Har­ris gladly accepted the esti­mated $90,000 ring, only to sell it after break­ing off their engage­ment just days before the wedding.

Many peo­ple thought she had finally come to her senses about mar­ry­ing a man who was 60 years older. But alas, they rec­on­ciled about a year later, and Har­ris got another ring cour­tesy of her sugar daddy—this time it was a five-carat dia­mond sur­round by 1.5 carats of smaller dia­monds on either side, set in a plat­inum band, esti­mated to be worth up to $1.0 mil­lion. Har­ris and Hefner offi­cially tied the knot on Decem­ber 31, 2012, and have been mar­ried ever since.

To put the age gap in per­spec­tive, Har­ris is 34 years younger than Hefner’s eldest child. The sugar daddy has acknowl­edged the fact that he won’t be around forever—especially now that he’s clos­ing in on 90—and he’s doing what­ever he can now to make sure his sugar baby wife is well taken care of after he passes. That’s why he dropped $5.0 mil­lion on a man­sion that’s sit­ting in a trust, just so that Har­ris will have some­where to go when she’s no longer enti­tled to rule the Play­boy Man­sion as Mrs. Hefner. The best part? Har­ris doesn’t tech­ni­cally have to wait for Hefner to die in order to ben­e­fit from the house—if he out­lives their mar­riage, she’s still enti­tled to her share.

Hugh Hefner and Crys­tal Har­ris, 60-Year Age Dif­fer­ence, 2.0 out of 10 based on 1 rating