Relationship Details

Celebrity Biographies

Hugh Hefner dated Kendra Wilkinson in the past, but they broke up in October, 2008. Hugh Hefner dated Kendra Wilkinson for 4.5 years. Hugh Hefner is currently married to Crystal Harris.

Hugh Hefner Profile Photo

Hugh Hefner

Media - Publisher

Why Famous: CEO of Playboy Enterprises

Age: 90 (b. 4/9/1926)

Hugh Hefner Photos (5)

Hugh Hefner's Relationships (31)

Kendra Wilkinson Profile Photo

Kendra Wilkinson

Porn Industry - Playboy Model

Why Famous: The Girls Next Door

Age: 31 (b. 6/12/1985)

Kendra Wilkinson Photos (24)

Kendra Wilkinson's Relationships (5)

Relationship Timeline

Event Start Date Length
Dating 4/2004 4.5 years
Broke Up 10/2008 --
 Total4.5 years

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Relationship Information, Quotes, and Trivia

Where and/or how did Hugh Hefner and Kendra Wilkinson meet?

Wilkinson met Hugh Hefner at his 78th birthday party in April 2004, where she was hired to be one of the "painted girls" (women who are nude except for painted-on accessories). Hefner had apparently seen her picture, shot by photographer Kim Riley, on a fax machine at the Playboy Mansion and wanted to know who she was. Shortly after they met, Hefner asked Wilkinson to be one of his girlfriends, and he moved her into the Playboy Mansion along with her dogs, Raskal and Martini.

Why did Hugh Hefner and Kendra Wilkinson break up?

She moved out of the Playboy Mansion in 2009 after meeting her future husband, Hank Baskett, and filmed her own spin-off reality show for E! called Kendra. The first season was about her living on her own and planning her wedding.

Other Relationship Information about Hugh Hefner and Kendra Wilkinson:

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Classic Quotes by Hugh Hefner and Kendra Wilkinson about their relationship:

"I have given her my blessing, and will be giving her away at a very special wedding ceremony at the Playboy Mansion this coming June." Hugh Hefner 11/24/2008
"I was living in San Diego with my boyfriend. I was a dental assistant, but I quit and we just lived together. As soon as I turned 18, I got my boobs done. Not for Playboy, for myself. I went from a small B to [a] 36C. I was at a car show and a guy came up and was like, 'Hey, would you like to do a photo shoot?' And he put my pictures on his website. Hef sees my picture and goes, 'Get this girl's number. I want this girl to be a girlfriend.' He paid for a limo to come get me every weekend. My life was just kinda boring, not going anywhere. One weekend I just packed up my bags and said, 'I gotta go. I have to start exploring my life.' My mom was completely against me moving. She though they had orgies up there!" Kendra Wilkinson 1/26/2009
"Even though I'm a tough bitch, it was scary at first being around in the plastic Hollywood thing. I felt like nobody really liked me for who I was, and I had to change who I was a little bit for them to accept me. I wore tons of makeup and dyed my hair from blonde to Playboy-white. I was that girl. I changed. At first I felt Holly and Bridget hated me. When I got there, Bridget was in Room 3 and Holly was in Hef's room. They asked me, 'What room did Hef give you?' When I told them Room 2, they were like, 'No, no you're not.' They had already made plans to turn it into a scrapbook room. But in the end I got it and there was no more drama. We were never best friends, but it was cool getting to know them. We're sisters." Kendra Wilkinson 1/26/2009
"Age ain't nothing but a number. Hef made me feel beautiful and his eyes on me made me feel so good. He looks at the most beautiful women in the world every single day, and it's crazy to think he considered me one. I'm like a dude, you know? I'm like a total tomboy." Kendra Wilkinson 1/26/2009
"Besides the nights we went out, I only saw Hef, like, once a day walking through the halls to his office. There were never solo dates. Thank God. I wouldn't know what to do! It's so intimidating talking to Hef one-on-one. The most we kind of say to each other is, 'I love you,' 'Love you too,' 'I hope you have a good day,' 'Did you have a good day?' But past that, I was intimidated. There were romantic times, but I never saw a future with us, and I always knew it was gonna end, so I had to plan for my future. I never stopped hanging out with my guy friends. I had to have sex every now and then, so I had to kind of sneak it. Hef was kind of like my best friend, but a sugar daddy at the same time. He would give me diamond bracelets and stuff." Kendra Wilkinson 1/26/2009
"[I had] to be Hef's arm candy and look good for him and be classy. Fridays, Saturdays, and Sundays, it would be dinner and a movie, and you have to go. Hef would write notes about the movies and he would read them at the screenings. He has all these guys who are all the same exact age as him, and it was like, 'Oh, my God, I have to sit here and talk to all these 80-year-old men who I don't relate to?' I was going crazy." Kendra Wilkinson 1/26/2009
"Hef helped my soul grow up. He's like my mentor." Kendra Wilkinson 1/26/2009
"I feel like I am one of the only ones who has walked into his life that he loved for me. Not for bleached-blonde hair and big boobs. At first, yeah, but then he really got to know my soul." Kendra Wilkinson 1/26/2009
"Now I'm totally against his way of life, with three girlfriends and all of that." Kendra Wilkinson 1/26/2009
"I hope Hef finds real happiness and not something just to rebound and make things feel better. I want classy people around him who don't do drugs, steal cheat, lie." Kendra Wilkinson 1/26/2009
"[I met Hank] in March, during the Playboy Golf Scramble in Palos verdes, California. We hit it off and started dating right around my birthday. That's when we really started falling in love. I didn't tell Hef because I didn't want to make all these decisions and then be fucked at the end. I wanted to make sure Hank was for me and loved me for me. After the stuff about Holly's relationship with Criss Angel came out, the press caught Hank and me at a romantic dinner, so I was finally open with hef. I said, 'Look, I really love this guy Hank, and I think it's time for me to move on. I don't want to make you look bad, so I'm gonna move out, and we'll be friends forever.' He had been blindsided by the Holly and Criss Angel thng, and that hurt him so much that when my thing came out, he really didn't care that much. He knew it was coming." Kendra Wilkinson 1/26/2009
"I might have second thoughts [about Hef walking me down the aisle]. I feel like it would be more appropriate if I ask my brother to walk me down the aisle, maybe at a country club or on a yacht. No offense to Hef. Of course I want him at my wedding, but I'm ready to be done with Playboy. I'm ready to be a classier woman, a wife and a mom. At Playboy, I was a crazy-fun party girl, and now I'm ready to be a lady." Kendra Wilkinson 1/26/2009

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