8. Hugh Hefner And Crystal Harris
Hugh Hefner was a notorious playboy, which was no surprise from the founder of Playboy magazine. When he was well into his eighties, had been divorced two times, and ran through a countless list of young and beautiful girlfriends, Hugh met Crystal Harris. Harris was 26 years old when she first captured Hef’s eye in 2008 at a Halloween party at the Playboy Mansion.
By December 2010, the couple was engaged. Hef had moved all of his other girlfriends out of the mansion and Crystal had become his number one woman. However, their first engagement did not exactly work out. Just a week before their planned wedding, Crystal got cold feet and called the whole thing off. She even spoke out against Hugh publicly with defamatory comments, but the two ended up working things out. Their wedding took place at the Playboy Mansion in 2012. Hefner 91 when he died in September 2017 and Crystal, 31, was not left with much in the millionaire’s will after being married for nearly five years.
7. Macaulay Culkin And Mila Kunis
Many people were surprised to learn that Mila Kunis had dated Macaulay Culkin for nearly ten years. The celebrity couple kept a low-profile while they were together and while it was known that they were dating, they were rarely photographed so the public was not often reminded of their relationship. Kunis is one of the most beautiful actresses in the world. Granted, at the time, she had not found her big break in films just yet but she had already starred on That ’70s Show and was making a name for herself.
Culkin was a washed-up child actor who looked like he had a serious drug problem, appearing frail, pale, and tired. However, at the time that they were dating, Culkin was still a much bigger star than Kunis. Kunis is now a huge celebrity and has starred in countless Hollywood hits, far surpassing Macaulay’s fame. She is happily married with children to her That ’70s Show co-star, Ashton Kutcher.
6. Anna Nicole Smith And J. Howard Marshall
Anna Nicole Smith was a Playboy model who captivated the country’s attention with her high-profile case, taking her late husband’s family to the Supreme Court in order to gain control of his billion-dollar fortune. Smith also happened to be 63 years younger than her husband, J. Howard Marshall. Marshall was an oil tycoon and she met him when she was in her twenties at a club she worked at in Texas.
Obviously, people assumed that she had only married the man for his money but Anna Nicole insisted she was getting her happily ever after. However, just one year after getting married, Marshall passed away and did not even include Smith in his will. Anna wound up teaming up with Marshall’s youngest son, who had been disinherited, in 1995 to challenge the will in hopes of winning control of the money. Although, Marshall’s oldest son Pierce was determined to stop the pair from ever getting hands on his father’s fortune. Smith actually ended up dying as well, after years of struggles with addiction and weight issues.
5. Angelina Jolie And Billy Bob Thornton
Angelina Jolie married her second husband Billy Bob Thornton in 2000. The scruffy, salt and pepper-haired actor and the ravishingly gorgeous actress were an odd sight to see. The two met on the set of Pushing Tin, a film where the actors played an eccentric married couple. After that, the two were inseparable and appeared everywhere together.
This is also the time when Jolie and Thornton displayed their matching pendant necklaces prominently around their necks, which contained the other’s dried blood. The couple got divorced just a few years later in 2003. Jolie claimed that “it was not meant to be,” while Thornton has said that it was not easy being with the most beautiful woman in the world and that he did not feel like he was ever good enough for her.
4. Chelsea Handler And 50 Cent
The witty blonde bombshell comedian and the talented rapper who started out on the streets have little in common but the public was very infatuated with their relationship back in 2010 after the “21 Questions” singer appeared on her late-night talk show. Chelsea Handler and 50 Cent had a connection that no one can deny and the two are still fairly close to this day.
In 2014, the musician posted an Instagram picture of an exposed Handler, saying that his love for her was “out of control.” Although both of the celebrities have had nothing but wonderful things to say about one another, their relationship did not last long. Chelsea and 50 got into an argument which led to their breakup but that clearly did not have an impact on their lasting friendship.
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