Hugh Hefner, the iconic founder of Playboy, and Crystal Harris, a former Playboy Playmate, captivated the public with their high-profile and often scrutinized relationship. With Hefner 60 years older than Harris, many looked down on their relationship and believed Harris was only after Hefner’s fortune. Nevertheless, the two pushed forward with their love and were married until 2017, when Hefner sadly passed away.
Crystal Harris has since claimed that she’s ready to drop Hefner’s last name, and published a tell-all memoir in January 2024, titled, Only Say Good Things: Surviving Playboy And Finding Myself. It’s been met with mixed reviews, but Harris definitely dropped a few bombshells. This article traces the fascinating timeline of their journey through love, commitment, and the challenges they faced.
2008-2009: Initial Meetings And Moving Into The Playboy Mansion
Hugh Hefner and Crystal Harris met at Hugh’s 2008 Halloween party. Crystal, 22 years old at the time, was introduced to Hugh, and despite the incredible age difference, the two hit it off pretty quickly. Their connection quickly evidently deepened, and Harris became a regular presence in Hefner's life. That same month, Harris was named “Co-Ed Of The Month” on Playboy.com. By January 2009, Harris began dating Hefner and moved into the Playboy Mansion. There, she lived with Hugh and his other two girlfriends, the twin sisters Karissa and Kristina Shannon. In October of the same year, Harris made her debut on Girls Next Door. Two months later, she was crowned “Playmate Of The Month.”
2010: Hugh Proposes To Crystal Harris
On Christmas Eve 2010, Hefner proposed to Crystal Harris with a 3.39-carat engagement ring and Harris said yes. Evidently, despite Hugh’s two previous marriages, he was still willing to give love a chance. Soon after, the couple announced their engagement to the public. Hefner posted on Twitter, stating: “When I gave Crystal the ring, she burst into tears. This is the happiest Christmas weekend in memory.” The news shocked many and the announcement of their engagement raised many eyebrows, especially considering their age gap. While Hefner was known for his many girlfriends, marriage was rarely a step for the casanova. As a result, many believed the 22-year-old was solely attracted to Hefner for his extensive wealth associated with Playboy.
June 2011: Crystal Harris Calls Off The Wedding
Even though Hefner was ready to spend the rest of his life with Harris, it seemed she did not feel the same way. Mere days before they were scheduled to exchange vows, Crystal decided to cancel the wedding. She went on to speak on Entertainment Tonight a few days later, explaining her decision. “I wasn't the only woman in Hef's life,” she said. “I didn't feel comfortable in my heart knowing that and getting married to him because a marriage is between two people.”
July 2011: Throwing Shade
Just a month after the wedding was canceled, Crystal went on Sirius XM’s Howard Stern Show. There, she threw shade at her former fiancé and their sex life. “The sex lasted like two seconds. Then I was just over it,” she said. She ended by claiming she “walked away” and was “not turned on by Hef.” The information did not shock many, especially considering Hefner’s age at the time. Nonetheless, Hefner took the matter to heart and fired back in a now-deleted tweet. “For the record, I have sex on a weekly basis. And I did throughout my two-and-a-half years with Crystal.” The pair were ultimately believed to be over, and for months, did not exchange words publicly.
2012: Hugh Hefner And Crystal Harris Reconcile And Exchange Vows
Surprising many, Hefner and Harris reconciled in mid-2012. Moreover, they announced their renewed engagement. Harris tweeted that she was “his #1 girl again,” and that they were both happy. Hefner went more in-depth about how they reconciled in his own tweet, however. “It's Mary O'Conner that brought Crystal Harris back. Crystal was miserable and said so. Mary told Crystal to write and tell me, which she did,” he wrote.
Hugh Hefner and Crystal Harris finally tied the knot on December 31, 2012, in an intimate ceremony at the Playboy Mansion. The wedding was attended by Harris’ family and Hefner's four children. Unsurprisingly, it was reported that Crystal was required to sign an “iron-clad” pre-nuptial agreement. This was in an effort to safeguard Hefner’s massive fortune.
2013: Enjoying Married Life
Throughout 2013, Hugh Hefner and Crystal Harris were photographed attending various events together, portraying a united front. The couple's lifestyle, which included a bustling social calendar and the glamorous world of Playboy, was closely followed by the media. Despite her previous confidence, Harris was elusive when discussing their intimate life post-marriage. Nonetheless, they remained heavily on the paparazzi’s radar that year. As time went on, media coverage on their lives began to dwindle.
December 2014: A Welcoming Christmas Tour
To share in the holiday spirit, Harris provided fans with an exclusive glimpse into the holiday festivities at the Playboy Mansion. Posting the tour on YouTube, Harris stated: “It’s the best time of year not just ’cause of gifts and stuff, but because of my friends and because of [my Christmas tree] and because it’s just such a cozy holiday. I love it. Christmas is my favorite holiday!”
September 2017: Hugh Hefner’s Passing
The legendary Hugh Hefner passed away on September 27, 2017, at the age of 91. Crystal Harris mourned the loss of her husband, expressing her grief and gratitude for the time they had together. Speaking to PEOPLE after the funeral, she said: “I will feel eternally grateful to have been by his side, holding his hand, and telling him how much I love him. He changed my life, he saved my life. He made me feel loved every single day.”
2018-2023: Crystal Harris’ New Life After Hugh Hefner
Crystal Harris, now widowed, continued her life outside of the Playboy Mansion. Unlike what many people assumed, Hefner did not leave a large chunk of his fortune for Harris. She also eventually moved out of the Playboy Mansion to Hawaii. Harris soon ventured into different pursuits, and her post-Hefner life became a subject of interest for those who had followed their relationship.
2024: Starting From The Beginning
Harris’ tell-all memoir was published in January 2024. It detailed many events that happened in the Playboy Mansion, and away from the public gaze. Harris also spoke about how she was forced to conform to Hefner’s views and wants, both physically and emotionally. In an interview with CBS Mornings, Harris admitted to never loving Hefner. She said: “I don’t think it was love. I did care for him. He was getting older and I know he wanted to protect his image… I felt sorry for him in a way and I felt that he really needed me.” As aforementioned, the memoir has polarized the public.