But barring the obvious May-December oddness of the pairing, any breakup of a seemingly happy couple—especially one that was five days from making things official! Or at least some analysis, which is why we've composed this handy timeline of Hef and Crystal's romance, from it's boy-meets-girl-next-door beginning to the duly denied cheating rumors that foreshadowed the end: April 9, 1926: Hugh Hefner is born and, in 30 years' time, turns pajamas into formal wear and becomes the envy of millions of men around the world. Cameras capture him giving all three a quick smooch on the lips at a Lakers game and you can bet the announcers who comment are jealous. 24, 2009: In case you had forgotten that Hefner's lifestyle is somewhat unconventional, he reminds everybody that he's been married all this time by filing for divorce from onetime Playmate Kimberly Conrad.October 2008: Crystal Harris and twins Kristina and Karissa Shannon move into the Playboy Mansion after the reign of Kendra Wilkinson, Bridget Marquardt and Holly Madison comes to an end. He was hitched to his second wife and mother of his sons Marston and Cooper for 21 years, the final 11 of which they spent separated.She says yes and they announce their engagement the following day. "I do believe that if you are healthy, age is just a number," the certainly hale-seeming media tycoon says."It depends on your DNA and it also depends very much on how you are as a person, your mental attitude, et cetera."Feb. 1 Holly Madison admits that she has "a lot of different feelings" about Hef's engagement, telling E!
"If [Crystal] doesn't give me a save the date soon I'm going to have to put in my save the date with the other wedding," she threatened.Season 1 of Dating Naked came to an end with Episode 11, which was billed as “The Lost Episode.” This episode was actually the first episode filmed and included several differences from the other episodes of Season 1. It also served as a reunion episode, as many of the show’s previous naked daters returned for the festivities, including Joe from Episode 1, Chuck from Episode 4, Marcus from Episode 5, A. Episode 8 of Dating Naked introduced Philly native Mike (not to be confused with Episode 5’s Mike), who comes to the island looking for some romance. Another change is that the final ceremony occurs on the beach. Episode 10 of Dating Naked was billed as a wedding special, celebrating the union between Ashley and Alika, the couple who met in Episode 6. All five of the men, along with the groom Alika, showed rear nudity at points throughout the special.In the end, Keegan picked Jessie to explore romance with after his third date ended in disaster, and led to the show’s first ever on-air verbal tirade by a contestant.The biggest takeaway from the episode, though, is that Keegan is absolutely gorgeous.But later Liddy’s third date, former frat boy Steve, is introduced leading her attentions to stray. J., meanwhile, heads on naked dates with two other ladies, treating viewers to several nude scenes. VH1’s Dating Naked has officially been renewed for a second season.Here’s hoping there’s lots more hunks like the trio introduced in Episode 6. His first date with Ashley is uneventful leaving him ready to move on to the next ladies to visit the island.January 2010: Hefner stops romancing the Shannon twins and they move out. News that marriage to Harris is "certainly possible."Dec.March 2010: Hefner's divorce from Conrad is finalized, leaving him free to do whatever he wants. 25, 2010: Hef proposes to Harris, 24, with a 3-carat-plus ring. News that he has no misgivings about the 60-year age difference between him and his future missus.Equally commonly, the Hyde side shows up in the implicit or explicit threats: if you don’t do x, y and z to bend to the psychopath’s will, he will replace you with other women or abandon you.While in the beginning of romantic relationships psychopaths tend to be mostly polished, charming Dr.