Hugh Hefner Regrets Not Marrying Holly Madison — She's 'Loyal' & 'Kind!'

Wed, June 22, 2011 6:04pm EST by 8 Comments

Hef is feeling the pain following his split from fiancee Crystal Harris, and wishing he stayed with former lover Holly!

Hugh Hefner, 85, is pining for his ex-flame now that his engagement to much younger girlfriend Crystal Harris, 26, has been called off. She got cold feet just days before her $1 million wedding to the eternal playboy!

Earlier this year, former Playboy Playmate Holly Madison, 32, expressed her concern for Hef to Life & Style magazine, worrying that Crystal was “using him to start her career.” After she heard the engagement was called off, Holly went straight to the Playboy mansion to give Hef her support.

While she’s happy to be a shoulder to lean on, sources close to the reality star insist that she and Hef will never rekindle their romance, explaining, “That chapter of her life is closed.” Holly is now dating the managing partner of XS nightclub in Las Vegas, Jesse Waits.

So sad for Hef — he’s reportedly been telling people, “I should’ve married Holly.” — Too little too late!

–Paris Grimmond

Get More Hugh Hefner Gossip Here

  1. Holly Madison Attacks Crystal Harris On Twitter!
  2. Crystal Harris Breaks Down Over Hugh Hefner In Interview, ‘Relieved’ She Called Off Wedding.
  3. See Crystal Harris’ Sexy New Playboy Cover! Plus, Why She Left Hugh Hefner!

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Posted at 3:13 PM on October 3, 2012  

poop :(

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Posted at 8:22 AM on May 8, 2012  

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Posted at 11:26 AM on April 27, 2012  

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Posted at 1:06 PM on March 25, 2012  

I to the believe that Hef should have married Our Holly. She loved him and treated him like a king. Holly called it when she voiced her concern to Hef about his now ex fiancee and what her true intentions were. TEAM HOLLY FOREVER.

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Charleen Ramus

Posted at 5:33 AM on November 16, 2011  

Dear Hef,
If in fact you are a forward thinker , I ask you to look back and view the loyalty you once enjoyed in Holly. Perhaps you might ask yourself why you in all your selfishness couldn’t recognize a true spirit in Holly. I hope you are left the time to find such an indulgence.If not I trust your children might give you a sense of balance as I feel concern that your race for t&a have left you broke of the mark.Holly may have been your truth dude,god’s speed!!!!!

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Posted at 6:19 AM on July 27, 2011  

Crystal Harris looks like a guy. Hef definitely should have married Holly. Holly is the perfect woman.
Crystal is a bum. She should remain unemployed and living on the streets for all she has done to Hef.
Hef was punished for letting Holly leave. Worst mistake of his life.

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Posted at 2:43 AM on June 24, 2011  

*jealous blogger slant*

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Posted at 1:17 PM on June 23, 2011  

Hef should realize marriage again for him is crazy he needs all the ho’s that come in the mansion screened and back ground checked and keep his Social security checks in the vault..

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