{"id":17786,"date":"2025-03-23T15:03:49","date_gmt":"2025-03-23T15:03:49","guid":{"rendered":"https:\/\/ourtimenew.com\/?p=17786"},"modified":"2025-03-23T15:03:49","modified_gmt":"2025-03-23T15:03:49","slug":"hugh-hefners-ex-girlfriend-kendra-wilkinson-reveals-60-year-age-gap-relationship-has-left-her-with-problems-with-intimacy","status":"publish","type":"post","link":"https:\/\/ourtimenew.com\/?p=17786","title":{"rendered":"Hugh Hefner’s ex-girlfriend Kendra Wilkinson reveals 60-year age-gap relationship has left her with problems with intimacy"},"content":{"rendered":"

Kendra Wilkinson has opened up about the long-lasting effects her relationship with Hugh Hefner has had on her life.
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\nKendra Wilkinson has revealed how her 60-year age-gap relationship still affects her life. Credit: Amanda Edwards\/Getty Images<\/p>\n

The former Playboy model, now 39, was the youngest of the magazine mogul’s three girlfriends featured on their reality show, The Girls Next Door.<\/p>\n

At the time, Hefner was also dating Bridget Marquardt, now 51, and main girlfriend Holly Madison, now 45.<\/p>\n

Wilkinson had met Hefner at his 78th birthday party when she was just 18 years old, where she had been working as a ‘painted lady’, which involved her being nude except for body paint.<\/p>\n

She moved into the Playboy Mansion shortly after they met in 2004, and went on to remain living there until 2009.
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\nKendra Wilkinson (left) was one of Hugh Hefner’s three girlfriends, along with Bridget Marquardt (second left) and Holly Madison (right). Credit: Kevin Winter\/Getty Images<\/p>\n

Many of Hefner’s former girlfriends have spoken out about their experiences at the mansion, and Wilkinson has now shared how it still affects her sexual relationships.<\/p>\n

Speaking on the Amy & T.J. podcast, Wilkinson admitted: “Look, I struggle still to this day with my relationships and my views on sex.<\/p>\n

“I had to go through a lot of therapy, and they looked at me and they\u2019re like \u2014 this is the first time I\u2019m admitting this \u2014 but they\u2019re like, ‘You might have a little bit of a sex problem. You have a little bit of a problem when it comes to thinking of sex.'”<\/p>\n

Host T.J. Holmes asked the model-turned-real-estate agent how her relationship with Hefner – and their 60-year age-gap – as well as the “environment” she spent those formative years in affected her long-term.
\nHe asked: “Again, you\u2019re a teenager. You hadn\u2019t been necessarily exposed to healthy relationships at that point in your life, but it puts you on a certain path \u2014 what did that do to you and [how did it] shape what you thought a relationship was, should be, and the type of person you were interested in?”
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\nKendra Wilkinson admitted her 60-year age-gap relationship with Hugh Hefner still causes her ‘problems’ with intimacy. Credit: Denise Truscello\/WireImage\/Getty Images<\/p>\n

Wilkinson admitted it caused her to have “just unhealthy thoughts”, explaining: “Not really settling for a marriage and stuff like that.<\/p>\n

“Which is not, I wouldn\u2019t say unhealthy \u2014 I\u2019m saying that everyone has their choices, and some people wanna be single, some people wanna be married \u2026 and I\u2019m more of a fun idea type of person.”<\/p>\n

Wilkinson ended up leaving the mansion for good in 2009 after getting engaged to former Philadelphia Eagles star Hank Baskett, with the pair even holding their wedding ceremony at the Playboy Mansion.<\/p>\n

She revealed that after five years at the notorious property, she was ready to move on with her life, telling Holmes and co-host Amy Robach: “I found myself so bored at the Playboy Mansion.<\/p>\n

“I was just like, ‘I\u2019m ready to leave this place. I\u2019m ready to start a family. I\u2019m ready for the lifestyle: My kids go to a great school. I\u2019m a soccer mom. I\u2019m a softball mom. I\u2019m a basketball mom.’<\/p>\n

“I manifested it, and it came to me, and I met the perfect man, the man of my dreams.”
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\nKendra Wilkinson and Hank Baskett share two children. Credit: Joe Scarnici\/Getty Images<\/p>\n

Though she and Baskett ended up divorcing in 2018, she still recalls those times as “the golden years” of being a wife and a mother.<\/p>\n

She admitted: “When those days came to an end, I crumbled so hard and it almost killed me. It almost killed me.”<\/p>\n

Despite their break-up being sparked by cheating allegations, Wilkinson and Baskett have managed to maintain a great relationship as co-parents.
\nShe explained: “Even though we\u2019re divorced, he\u2019s the father of my kids and he\u2019s the most amazing father to my kids, and I know I chose right with him.”<\/p>\n

Wilkinson and Baskett share two children – son Hank, 15, and daughter Alijah, 10.<\/p>\n","protected":false},"excerpt":{"rendered":"

Kendra Wilkinson has opened up about the long-lasting effects her relationship with Hugh Hefner has had on her life. Kendra Wilkinson has revealed how her 60-year age-gap… <\/p>\n","protected":false},"author":1,"featured_media":17787,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[1],"tags":[],"class_list":["post-17786","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-uncategorized"],"_links":{"self":[{"href":"https:\/\/ourtimenew.com\/index.php?rest_route=\/wp\/v2\/posts\/17786","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/ourtimenew.com\/index.php?rest_route=\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/ourtimenew.com\/index.php?rest_route=\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/ourtimenew.com\/index.php?rest_route=\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/ourtimenew.com\/index.php?rest_route=%2Fwp%2Fv2%2Fcomments&post=17786"}],"version-history":[{"count":1,"href":"https:\/\/ourtimenew.com\/index.php?rest_route=\/wp\/v2\/posts\/17786\/revisions"}],"predecessor-version":[{"id":17791,"href":"https:\/\/ourtimenew.com\/index.php?rest_route=\/wp\/v2\/posts\/17786\/revisions\/17791"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/ourtimenew.com\/index.php?rest_route=\/wp\/v2\/media\/17787"}],"wp:attachment":[{"href":"https:\/\/ourtimenew.com\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=17786"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/ourtimenew.com\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=17786"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/ourtimenew.com\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=17786"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}