If he had had his way, Hugh Hefner would have exchanged vows with Crystal Harris in the summer of 2011.
But the Playboy founder says he won't be making that same mistake in the new year, telling People this week that he "dodged a bullet" when Harris dumped him days before their scheduled June wedding.
Hugh Hefner and Crystal Harris are involved in a major doggy dilemma. A canine conundrum. A puppy problem for the ages... literally!
While this couple narrowly avoided a wedding in June - when the young blonde essentially stood her much elder fiance up at the altar - and while they have little contact with each other at this point, Hefner tells People Magazine there's still one very cute point of contention between him and his ex.
Hugh Hefner believes Lindsay Lohan's Marilyn Monroe-themed Playboy pictures will make the new issue a keepsake - proving some people wrong, including himself.
"The concept came from my editors," Hefner told People in a recent interview.
Not unlike the men it is marketed toward, Lindsay Lohan's Playboy spread will come early this month. Hugh Hefner confirmed the news on Twitter Friday.
"Because of the interest & the Internet leak, we're releasing the Lindsay Lohan issue early," Hugh said after the leak of the Lindsay Lohan Playboy pictures.
Hugh Hefner may have given it to Crystal Harris on multiple occasions, but the Playboy founder's former fiancee is about to give it right back to her ex - but giving away his engagement ring!
TMZ has actually posted the listing for this 3.39 carat rock, which will go up for auction in October at Christie's, a famous auction house in New York City. It's expected to fetch between $20,000 to $30,000.
Hugh Hefner has an important point to make: He has totally made love to Crystal Harris. Multiple times!
In a new interview with The Hollywood Reporter, the Playboy founder goes into way too much detail about this insertion as a response to his ex-fiancee claiming over the summer that she wasn't attracted to Hef and he was only inside of her for like two seconds one time.
Kendra Wilkinson just doesn't get it.
Granted, this former Girl Next Door opened up about her relationship with Hugh Hefner in the memoir "Sliding Into Home," but her situation can't compare to that of Crystal Harris. Why?
Crystal Harris, you've messed with the octogenarian.
That's the message Jayde Nicole has sent to Hugh Hefner's former fiancee, after Harris humiliated the Playboy founder by telling the world he only lasts for two seconds in bed.
During an appearance on Howard Stern's radio show this week, Crystal Harris said she wasn't attracted to Hugh Hefner, she never saw him naked and they only had sex once, with it lasting for like "two seconds."
Now, the busty blonde has something to tell her former fiance: My bad!
Crystal Harris made news this week for saying Hugh Hefner can't satisfy a woman.
But a couple Playmates have come out and stood up for the magazine magnate by saying he definitely knows what to do when girlfriends are lying down.
Don't pity Hugh Hefner, folks.
Granted, the 85-year old didn't exactly make Crystal Harris scream during their time together. But the Playboy founder says his ex-fiancee is the one who needs your sympathy, following a revealing interview with Howard Stern in which Harris slammed Hef's stamina.
Crystal Harris appeared on The Howard Stern Show this morning and had nothing flattering to say about ex-fiance Hugh Hefner. At all.
Asked by the host how long it took for the pair to consummate their relationship, Harris replied "two seconds." Perhaps even more incredible? That's one more second than number of times the pair actually did it!
Hugh Hefner is a twice-divorced 85-year old who strolls around his mansion all day in a bathrobe, attached to multiple beautiful women.
So why the heck did he ever contemplate marrying Crystal Harris?!? The magazine magnate has no idea, he admits in a new interview with Entertainment Tonight.
Crystal Harris is a 25-year old blonde with an aspiring singing career who chose not to marry an 85-year old who spends all day in a bathrobe.
Tomorrow night at 10 p.m. EST, Lifetime will spend an hour exploring the reasons behind this shocking split.
Yes, Anna Sophia Berglund is Hugh Hefner's "best girl." That's what the Playboy owner labeled Miss January 2011 as late last month.
But, no, that doesn't mean Berglund is actually getting it on with someone old enough to be her grandfather, at least not according to a woman who really doesn't want that rumor to be true: Anna's mother.
Sorry, reader. But you're no Hugh Hefner.
That 85-year old has charm, millions in the bank account and a silk bath robe that drives the ladies wild. As a result, he can date both Anna Sophia Berglund (referred to this week as his "best gal") AND Shera Bechard (labeled by Hef as his "new girlfriend" yesterday).
Move over, Anna Sophia Burgland. Not too far. Just a little closer to the edge of the bed.
Just a couple days after Hugh Hefner labeled this Playmate as his "best girl," the magazine magnate has Tweeted that he has a "new girlfriend." Say hello to Shera Bechard!
His love life in flux, Hugh Hefner aimed to clear things up yesterday. In response to a fan question, the 85-year old Tweeted:
"With Crystal gone, Anna is my best girl. Anna is really one in a million."
Congratulations are in order for Shera Bechard. We guess.
Playboy's Miss November 2010 has been promoted by boss Hugh Hefner: she's now his number-two girlfriend!
Hugh Hefner thought he'd be a married man today.
But the Playboy founder was dumped by Crystal Harris just days prior to their wedding, and then watched as the woman he made famous partied and posed at an event in Las Vegas.
When you're 85 years old, you don't have much time to sulk over a broken heart.
In his quest to move on from Crystal Harris, Hugh Hefner has reportedly rolled over and found another serious girlfriend. Her name is Anna Sophia Berglund, she was Playboy's Miss January 2011 and she's already moved in to her boss' bed!
Hugh Hefner is a really nice guy and reeling emotionally after being dumped by Crystal Harris, but that didn't stop him from gaining a little revenge.
The publisher is making sure all copies of July's Crystal Harris Playboy cover come with a giant asterisk of sorts - a red "RUNAWAY BRIDE" sticker!
Was Crystal Harris cheating on Hugh Hefner with Dr. Phil's son, Jordan McGraw? Does she really want a career in music? Why is it surprising news that a 25-year old would choose not to marry an 85-year old?
Yes, there are numerous questions surrounding the split of Harris and Hefner, mostly because it took place five days prior to their wedding date.
It's definitely over for Crystal Harris and Hugh Hefner.
The Playboy founder acknowledged via Twitter yesterday that his 25-year old fiancee walked out on him five days prior to their wedding, and now Harris has also confirmed the split.
