Some of you may be surprised, while some of you may start sleeping better at night. 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!—is cause for a bit of sadness.
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.
October 2008: Crystal Harris and twins Kristina and Karissa Shannon move into the Playboy Mansion after the Girls Next Door reign of Kendra Wilkinson, Bridget Marquardt and Holly Madison comes to an end. Harris becomes Hef's new No. 1 girlfriend. 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.
Sept. 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. 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.
January 2010: Hefner stops romancing the Shannon twins and they move out.
March 2010: Hefner's divorce from Conrad is finalized, leaving him free to do whatever he wants. Finally.
April 2010: Hefner tells E! News that marriage to Harris is "certainly possible."
Dec. 30, 2010: The Playboy visionary assures E! News that he has no misgivings about the 60-year age difference between him and his future missus. "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. 5: Former No. 1 Holly Madison admits that she has "a lot of different feelings" about Hef's engagement, telling E! News she isn't sure whether she will attend the wedding or not.
March 3: Kendra, who tied the knot at the Playboy Mansion herself in June 2009, wonders aloud to E! News why the heck she hasn't received her save-the-date notice yet. "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.
March 23: Rumor has it that Harris is stepping out on her fiancé with Dr. Phil McGraw's son Jordan, who's a record producer. And Harris is an aspiring singer, so...you know! All was denied, with a Playboy Enterprises rep assuring the world that Harris and McGraw were just friends, and Hefner himself said there was "no truth to the gossip."
April 14: An appeased Kendra says Hef, upon hearing of her concerns, immediately emailed her to assure her that she'd be getting a formal invite, even telling her they'd change the date if she couldn't make it.
May 4: Hef tweets a picture of the couple's calligraphic wedding invitation, which requests "the pleasure of your company" at the Playboy Mansion on June 18. (So, like, wedding was still on.)
June 13: Harris bolts, with her manager calling it an "amiable split."
June 14: Hef confirms via Twitter that the wedding is off. (And, we like to think, breaks out his not-so-little black book and starts looking for new housemates.)
June 14: Harris posts this message on her website: "After much deep reflection and thought I have decided to end my engagement with Hef. I have the utmost respect for Hef and wish him the best going forward. I hope the media will give each of us the privacy we deserve during this time."
June 14: Uh-oh. Jordan McGraw's name surfaces again, but any unsavory suspicions are deemed "categorically untrue" by Harris' manager, Michael Blakey. "It's nonsense and has nothing to do whatsoever with the split," he tells E! News. A rep for McGraw says he has no comment on the story.
—Additional reporting by Ashley Fultz