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Holly And Kendra’s Complicated History


Over the past year, Holly Madison and Kendra Wilkinson-Baskett have spoken publicly about their contempt for one another.

The former Girls Next Door co-stars didn’t always have such bad blood between them, at least, it certainly didn’t seem that way.

To an outsider, Kendra and Holly appeared to be friends, or at the very least, friendly. This wasn’t the case, though, according to Kendra and Holly.

So when exactly did things go awry between the Playboy Mansion roomies? In order to figure that out, let’s take a look back at their friendship/frenemy timeline.


Holly and Bridget Marquardt began dating Hugh Hefner around the same time, but it was Holly who became his No. 1 girlfriend. Over the course of her 6-year relationship with the Playboy mogul, Holly made it clear she hoped to eventually marry Hef.


Kendra first met Hef when she was hired to appear in body paint at his 78th birthday party. Shortly thereafter, Hef asked her to be one of his girlfriends and invited her to move into the mansion.


Holly, Kendra, Bridget and Hef (to a lesser degree) began filming The Girls Next Door, which premiered in the fall on E!

“During that first season, Bridget, Holly, and I continued to keep our distance, except when we were filming,”

Kendra later recalled in her 2010 memoir Sliding Into Home.

“We did our thing off camera, and there was an unspoken competition for camera time when the cameras were around. Each of us wanted the others to look good and be successful, but whether they will admit it or not, I think we each wanted the spotlight and to look the best in every episode.”

The Girls Next Door aired for six seasons.


Kendra and Hank Baskett got engaged in the fall with Hef’s blessing. The Girls Next Door star subsequently moved out of the mansion but continued to appear on the show alongside Holly and Bridget.


On June 27, Kendra married Hank at the Playboy Mansion. Both Holly and Bridget were bridesmaids. The wedding

“was awesome and the craziest reunion,”

Holly told E! News at the time.

Bridget noted that “Holly cried like a faucet” while she “held back tears.”

Shortly after saying “I do,” Kendra revealed she was pregnant with her and Hank’s first child.

In September 2009, both Holly and Bridget celebrated with Kendra by throwing her a baby shower.


Although Holly and Kendra had gone their separate ways at this point, they weren’t yet at odds publicly.

Holly, who competed on Dancing With the Stars in 2009, publicly supported Kendra’s bid for that Mirror Ball Trophy.

“She absolutely has a chance at winning,”

she told People.

“She’s a natural athlete and she’s really competitive and she has a fan following, so I think she’ll do really well and certainly better than I did.”


The pot hadn’t boiled over quite yet, but it seems like the heat was increasing.

In 2012, Kendra told CNN things had just been “awkward” with her, Holly and Bridget because they all dated Hef at once,

“so, it’s not like it was a sorority house or like a sisterly bond…we were never even really friends to begin with, we all just kind of lived together and knew each other, so we’re all in each other’s lives.”


Holly released Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny in June.

The book included shocking allegations about Hef and life at the mansion (all of which he adamantly denied).

Kendra, who Holly described as

“the fakest person I’ve ever met,”

publicly defended Hef.

She also denied ever having been friends with Holly in the first place, telling E! News,

“At the end of the day, what we did was we just f–ked the same man. That’s not friends.”


Tension between Holly and Kendra has continued to escalate. Holly’s book “The Vegas Diaries” comes out later this month, and although it has yet to be released, the press tour surrounding it is already stirring up drama.

In an interview with People, Holly explained she has no interest in reconnecting with Kendra, saying,

“I wish her the best, but I’m done with that portion of my life. I’ve moved on. I’m happier now. I don’t think there would be anything positive about us meeting up. It’s not a real friendship and it’s not part of my life anymore.”

Kendra caught wind of the interview and responded to Holly in series of vulgar tweets (which have since been deleted).

Holly responded with a statement of her own, telling E! News,

“I’ve written a book,The Vegas Diaries, that’s about letting go and moving on. About resolving the past so you can live a future. I’ve dealt with my demons and I’ve come out ahead. I can hold my head high and work hard to be the classy and kind person I aspire to be. I want no part of a one-sided argument or feud where one woman lives to demoralize and degrade another woman.”For those with unresolved issues, therapy works. You should try it.”

Kendra responded about an hour later.

“I know my recent posts were a little over the top and I apologize for that,”

she told her followers after having deleted her NSFW tweets.

“Sticking up for me n my beliefs is hard for me at times. Sorry.”

Rebecca Macatee

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