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In January 2009, Crystal started dating Hugh Hefner, who was 60 years her senior. She joined the Shannon twins after his previous "number one girlfriend", Holly Madison, had ended their seven-year relationship. On December 24, 2010, she became engaged to Hefner, to become his third wife. Harris broke off their engagement on June 14, 2011, five days before their planned wedding. In anticipation of the wedding, the July issue of Playboy, which reached store shelves and customers' homes within days of the wedding date, featured Harris on the cover and in a photo spread, as well. The headline on the cover read "America's Princess, Introducing Mrs. Crystal Hefner." Hefner and Harris subsequently reconciled and married on December 31, 2012. She remained married to Hefner until his death on September 27, 2017. In 2016, Harris announced on her social media outlets that she had been diagnosed with Lyme disease and toxic mold before finding her symptoms were also due to "breast implant illness". Hefner stated that she experienced "brain fog" and "chronic fatigue" due to the implants but had them removed, which alleviated some of the symptoms
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