18 Things Hugh Hefner Has Taught Us About Relationships

The famous octogenarian has had more conquests than most. Lucky for everyone, he’s an open book.

Kate Dries 3 months ago 40 responses

The Many Loves Of Hugh Hefner

Lifelong ladies man Hugh Hefner finally married Crystal Harris on New Year’s Eve. In honor of their recent nuptials, let’s take a look at the other ladies in Hef’s past.

Louis Peitzman 4 months ago 84 responses

Hugh Hefner And Crystal Harris Wed On New Year’s Eve

It all went down at the Playboy Mansion last night. (Crystal is the one who left Hugh just five days before they were supposed to get married last year.)

Whitney Jefferson 4 months ago 113 responses

Meet Sherlyn Chopra, The First Indian To Pose For Playboy

Sherlyn got the gig after she wrote a letter to Hugh Hefner asking to be in the magazine after pleading that no Indian has ever had the honor. Her issue comes out in November.

Samir Mezrahi 9 months ago 62 responses

Playboy October 2011 Issue Will Sell For 60 Cents!

The October 2011 issue of Playboy will sell for the same cost as the magazine during the 1960s…60 cents. Why? To pay tribute to the when the original Playboy Club was first opened and to promote the upcoming show, “The Playboy Club”. (via dailymail.co.uk) View Image ›

Yes, El Guapo! a year ago 13 responses

Horsemaning At The Playboy Mansion

We know that Hef embraces meme culture, so this comes as no surprise. Pictured here: Anna Sophia Berglund, Miss January 2011 (head). View Image ›

Mike Hayes a year ago 54 responses

Hugh Hefner Alters Cover Of Playboy After Crystal Harris Calls Off Wedding

Hugh Hefner, having already given the go ahead for a Playboy cover with the title “Mrs. Crystal Hefner,” slapped a sticker on top to reflect Crystal Harris getting cold feet. Turning lemons into a lemon party. Don’t look that up. Tawdry details of the non-wedding here. View Image ›

Gavon Laessig a year ago 94 responses

Hugh Hefner Tweets His Heartache

Hugh Hefner has taken to his Twitter after his fiance left him days before their wedding. She apparently left him for Dr. Phil’s son. View List ›

Matt Stopera a year ago 42 responses

Hugh Hefner Sees Justin Bieber’s Movie, Gets Laid

Nice. View Image ›

Matt Stopera 2 years ago 97 responses

Hugh Hefner Talks Virginity Loss, ‘Overcompensation’ Issues on huffingtonpost.com ›

Grandpa talks about his first time.

The Huffington Post 2 years ago respond

Hef’s Taking Playboy’s Privates Private on huffingtonpost.com ›

The publisher of Playboy magazine has agreed to accept a sweetened buyout offer from a partnership headed by founder Hugh Hefner, allowing the original playboy to fulfill his plans to take the company private.

Roger Brunswick 2 years ago 1 response

Former Playmate On Sex With ‘Dead Fish’ Hugh Hefner on huffingtonpost.com ›

Details about Hugh Hefner’s sex life you probably didn’t want to know.

The Huffington Post 2 years ago respond

Crystal Harris Tweets Pic of Engagement Ring on okmagazine.com ›

It is apparent that Hugh Hefner has money.

OK! Magazine 2 years ago respond

The Ultimate Dating Timeline of Hugh Hefner

Since Hef just got engaged… again… Daily Hot Chick thought it would be an appropriate time to timeline the girlfriends of the world’s most infamous Playboy. Here they are! View List ›

PopularNobodies 2 years ago 39 responses

Raw Deal for Holly Madison: Hef Is Engaged on thegloss.com ›

Looks like all those excuses Hef made for not tying the knot with his former girlfriend were just lies.

The Gloss 2 years ago respond

Hugh Hefner Got Engaged to Crystal Harris on thesuperficial.com ›

Hugh Hefner proposed to his 24-year-old girlfriend Crystal Harris. Neat.

The Superficial 2 years ago respond

Hugh Hefner Got Engaged to Crystal Harris on thesuperficial.com ›

Hugh Hefner proposed to his 24-year-old girlfriend.

The Superficial 2 years ago respond

Hugh Hefner and Playmate Crystal Harris Get Engaged on mtv.com ›

Hugh Hefner and Playmate Crystal Harris got engaged on Christmas Eve.

MTV 2 years ago respond

Hugh Hefner & Crystal Harris Got Engaged On Christmas Eve on starpulse.com ›

Playboy boss Hugh Hefner got engaged to a relative infant over the weekend.

Starpulse 2 years ago respond

Hugh Hefner Engaged to 23-Year-Old Playmate on hollywoodlife.com ›

He’s older than three of her.

HollywoodLife 2 years ago respond

Hugh Hefner on Twitter

Everybody, Hugh Hefner has made it to Twitter. The tweets aren’t quite as aged as Ivy Bean’s, BUT, is it an unfortunate happenstance that both Hugh and Ivy recently tweeted about playing dominoes? I think not… Read More ›

Brian Ries 3 years ago 1 response

Hef Wants Holly Back at the Mansion on thefablife.com ›

Aw, Hef says Holly is the love of his life! Sure hope those crazy kids can work it out. Check out a gallery of the lovebirds through the years at TheFabLife.com.

The Fab Life 4 years ago 3 responses

Hugh Hefner’s Christmas Card

Yeah, those sports bras are just bodypaint. Happy Holidays from Hef, Kristina and Karissa, everyone! View Image ›

Amanda Dobbins 4 years ago respond

Hugh Hefner’s New Twins

Yesterday Holly Madison, Hugh Hefner’s “longtime” girlfriend from the Girls Next Door posted on her Myspace that her and Hef have broken up. New speculation suggests that Hef is dating these two 19-year-old twins, Kristina and Karissa Shannon. It’s rumored that they could possibly be on next seasons totally new (and different) Girls Next Door . Check out this picture and notice Holly and Hef in the background. Scandalous. Also check out the twins Myspaces for more pics n’ shiz. View Image ›

Matt Stopera 4 years ago 1 response

Pamela Anderson Naked Cake Delivery

Last night on Girls Next Door 40-year-old Pamela Anderson delivered a cake completely naked to Hugh Hefner for his 82nd birthday. All Hef could say was, “you’re lookin’ good.” View Image ›

Matt Stopera 4 years ago respond

YouTube Playmate Submissions

Always wanted to flash your naughties in the pages of Playboy? Well, now the nudie mag (we mean “gentleman’s monthly”) has partnered with YouTube to pick a naked lady straight out of the teh Internetz to celebrate its 55th anniversary issue. With a tepid audience response and a dismally low number of video submissions, it looks like Grandpa Hef might want to stop trying to figure out “this damn computerbox.” Read More ›

Eliot Glazer 4 years ago respond