Sadly, like Gene Simmons before him, another icon of male sexuality has surrendered to marriage. Perhaps not monogamous marriage, that remains to be seen, but an ostensibly traditional Disney marriage.

A little history on Hef. He married a much younger Playboy Playmate before, Kimberly Conrad back in 1988. However that marriage was a bullshit marriage from the start, and was largely a result of Hef toning back his lifestyle after having a stroke a year or two earlier. Near-death experiences can change a guy, so after his stroke he toned his wild parties way back, handed day-to-day control of his Playboy empire to his daughter, and got married.

Of course, human beings are human beings, and the need for sexual variety is not something you can just switch off when you feel like it, especially for Alphas, so after very quickly cranking out two babies with his new young wife Tom Cruise style, he started fucking other women again, and eventually booted her ass out, moving her into a house next to the Playboy Mansion. However he did not get a legal divorce, a very interesting move on his part that I’ll revisit in a minute.

The rest of the story is familiar to most people. Hef started an ever-rotating coterie of live-in MLTRs, dating between three and seven women at any one given point in time. The Girls Next Door show was made featuring three of his live-in chicks, Holly Madison (his primary MLTR who always approached, but never quite got to, OLTR status) and Bridget Marquardt and Kendra Wilkinson (low-end MLTRs).

Throughout this period, Hef never got divorced. Interesting. Many people thought it was because deep down he still “loved” Conrad, but that’s the Disney answer.  Hef is a very intelligent guy and a very strategic thinker. I can only speculate here, but my guess is staying married was somehow easier for him financially and it gave him an easy “out” with other women, specifically Madison, who was constantly pressuring him to kick the other bitches out and marry her. “Hey baby, I love you, but I can’t marry you. I’m still married! I’d get divorced but I can’t because legally that means that the business would have to <blah blah complicated businessspeak blah blah>.”

When asked why he stayed legally married for so long, he mumbled some BS about not hurting his kids, but I am 99% certain that his decision to never get legally divorced from Conrad was a purposeful, calculated decision on his part, both for financial reasons and relationship reasons. It’s also clear to me that, at that time anyway, he never wanted to get married again.

But, alas, as men age things change. Maybe his increased health problems made him think about death. Or something. Regardless, in 2010 his divorce was finalized, and just nine months later he proposed to his latest chick, Crystal Harris. The timing of those two events is not a coincidence…when he wanted to get married, then he got a divorce. It was not the other way around.

Harris left him at the altar, almost literally, last year, and then did a LSNFTE, leaving him to pursue monogamy elsewhere, possibly returning to Dr. Phil’s son. Both Hef and Harris attacked each other publicly, her calling him disgusting and only lasting “two seconds” in bed, him calling her a liar, etc, etc. Not a big deal. He quickly scooped up two new MLTRs (Anna Sophia Berglund and Shera Bechard) and continued as normal.

Somewhere around late last year, Hef and Harris reunited, got engaged around December, and married on New Years Eve, essentially doing a 180 on everything bad they said about each other just a few months earlier. Stupid. (This is why you really need to THINK before you say shit publicly. If you’re not careful, it will come back around to bite you in the ass and make you look really fuckin’ stupid. Hef looks really, really bad for taking this woman back after all the crap she threw at him.)

So why did Hef act so silly? Why did he do all this? I don’t know for sure, but I have educated guesses. Gene Simmons surrendered to marriage because of his hardcore oneitis, the killer of men. I don’t think Hef had, or has, oneitis. My guess is that it’s simply his age. He’s 86, and could die any time, and I think he feels it. Perhaps he wants some level of normalcy in his life now that he’s at death’s door.

Unlike Gene Simmons, I don’t think Hef is going to try monogamy very hard, and I think (again I’m guessing) that little miss 26 year-old wifey understands that once the honeymoon period is over, Hef will be right back to fucking chicks on the side. Despite her shortcomings, Crystal Harris is not the over-33 demanding bitchfest Shannon Tweed is, making Hef’s marriage far less of a surrender than Gene Simmons’ was.

Lastly, I’m going to say what I’ve said many times before. Once a man hits age 60, and perhaps he realizes death is closer, and perhaps his body can’t do what it once did, and perhaps the testosterone isn’t quite as strong, and perhaps the sex drive isn’t what it once was, some of the rules start to change. Do I fault men over age 60 who get married and take a shot at monogamy? Yes and no.

Yes, because it’s still not going to make them happy, since being married to a beyond-NRE-phase bitchy shrew will make a man unhappy at age 65 just like it will at age 25.

No, because let’s be real here, if you get married past age 60, your marriage really might last “the rest of your life”. Not because of your great relationship skills, but because you’re going to die in a few years. It’s simple math. So for that reason I don’t quite have the problem with a man who’s 65 (much less 86) getting married and monogamous than I do with man who’s 20, 30, or 40 trying it. The 65 year-old guy is going to be dead in a few years. Those other guys have decades and decades of prime-time yet to live through and experience.

All of this comes back to this: One of your greatest goals in life, because it certainly is mine, is to be as young, healthy, and physically fit in your old age as humanly possible. When you hit your sixties, you want to look and be as young, fit, and vibrant as guys like Liam Nesson or David Hasselhoff, or better! If you end up old and drained and tired in your sixties, you’ll be more than likely to surrender to monogamy prison with some bossy bitch. We don’t want that, now do we?

6 Comments on “Hugh Hefner Married

  1. Another one bit the bullet. But if there’s anybody who’s earned the right to do whatever they want, it’s Hugh Hefner. He got married twice in his twenties as well, if I’m not mistaken.

  2. “Only lasts two seconds?”

    That’s not much of an insult. If I was 86 and survived a stroke I’d be happy that the plumbing still works at all. 🙂

  3. Hef is super wealthy and his business provides him with his choice of 20 something women that are using him for a career move. I’m 60+, wealthy(no where near as wealthy as Hef), but I’m not exposed to 20 somethings that want careers from me like Hef’s women. Via online I get women in there late 40s and early 50s. As women approach 60 and beyond they loss their female hormones, get fat and wrinkled. I fucked a woman who was 60(one of the slim ones) and another who was 53. What a difference in skin tone(wrinkled vs smooth skin) and vaginal lub. In addition if a woman in her 60s doesn’t use Hormone Replacement Therapy she starts to get vaginal atrophy which makes sex painful, especially with women who have not had any kids. I fear what’s going to be available to me when I hit my 70s and 80s…Yuck. BTW I’m in great shape, have a six pack and workout with weights 4x a week so I’m not one of those fat fucks in their 60s that you see at the gym and elsewhere.

  4. I’m not sure a guy in his 70s or 80s is able to fuck young chicks based on game alone. Some amount of Gold-digging pretty much has to be involved. In Hef’s case is not just a carreer thing but also an issue of inheriting a good amount of money when the guy dies (which is probably in less than 10 or 15 years). If I reach 70-80s and I still have an itch for young pussy I guess I’m going to bite the bullet and just fuck a bunch of scorts/golddiggers. Chances are I will have a lot of wealth accumulated by then so the money won’t be a problem.

  5. Dennis – I’m curious. Why would you think having sex with hot early-50 year olds would be any less doable at your age vs. age 70 or 80? I really don’t see a huge difference between the two situations, especially if you stay reasonably non-fat.

    Alejandro – I very reluctantly have to agree with you, at least a little. If you’re literally in your 80’s, nailing a hot 52 year old should be workable with game alone, but if you wanted to nail a hot 22 year-old, then yeah, you may have to throw a little money around. I don’t mean thousands of dollars, but the money may have to flow a little more than my usual $0 – $14 average meet-to-lay. It does indeed go back to having strong financial goals as a man.

  6. The reason Hef stayed married.

    You can not be sued for palimony if you are married.

    Your wife has more right to your money than you do

    or your “pal”.

    Adulteresses do not win palimony suits the wife does.

    And if you have a wife that is cool with you situation

    (she got a lot out of the deal) you are bullet proof……

Leave a Reply

To leave a comment, enter your comment below. PLEASE make sure to read the commenting rules before commenting, since failure to follow these rules means your comment may be deleted. Also please do not use the username “Anonymous” or “Anon” or any variation thereof (makes things too confusing).

Off-topic comments are allowed, but Caleb will ignore those.

Caleb responds to comments in person, but he only does so on the two most current blog articles.

Related Posts

Begin typing your search term above and press enter to search.