Hugh Hefner

The former Playmate dated Hugh Hefner from 2001 to 2008.

Things got crazy at the Playboy Mansion the other night, and Playmate Anna Sophia Berglund — Hugh Hefner’s new “number one” girlfriend — got the octogenarian to engage in a bit of planking.

Hugh Hefner's 25 year old fiancee called off the wedding yesterday just days before it was set to take place.  Do you think she got cold feet?  ~Erin Well, so much for that: Hugh Hefner confirmed Tuesday that his wedding to 25-year-old model Crystal Harris has been called off...

Last February, Hugh Hefner and his posse held a fundraising event at the notorious Playboy mansion. And as you probably have already heard, over 100 of the guests reported having pneumonia and flu-like symptoms after the evening's shindig came to a close. What caused this? The LA Health officials finally have the answer.

He's on his third attempt at marriage, and this time it might be true love. It appears that way because the millionaire isn't protecting himself with a prenuptial. I kind of agree that if you really do care for someone, losing them would be worse than losing your money. Good for Hugh!