May-December Relationships...... Here I've been concerned and what does Hugh do and do?

Very Simply, P U S S Y ! Originally Posted by WiLsOn

He can get that all day long without marriage. Here's what Kendra Wilkinson said about her first time with him:

One of the girls asked me if I wanted to go upstairs to Hef’s room. In my head I could hear my mom’s voice: ‘You know they have orgies there.’ I said “Okay, if I have to.” It seemed like every other girl was going, and if I didn’t it would be weird. One by one, each girl hopped on Hef and had sex with him… for about a minute. I studied their every move. Then it was my turn… it was very weird. I wasn’t thinking about how much older Hef was—all the body parts worked the same. I wanted to be there.

Not a bad deal if you can get it. So why marry for pussy? Maybe she's a very special and mature 24-year old that he feels a very strong connection with, but I find that hard to believe.

Yep, and you have to keep in mind that Hef is no fool. Just like the 80+ year old man that married the fat blond.. (what's her name that died from drug overdose). You don't get to be a BILLIONAIRE by being stupid. If ya got the $$$$$$$, and you want a young beautiful lady... who's to say "no"?
Maybe she IS sharp, and he really really likes her... stranger things have happened.

Yep, and you have to keep in mind that Hef is no fool. Just like the 80+ year old man that married the fat blond.. (what's her name that died from drug overdose). You don't get to be a BILLIONAIRE by being stupid. If ya got the $$$$$$$, and you want a young beautiful lady... who's to say "no"?
Maybe she IS sharp, and he really really likes her... stranger things have happened. Originally Posted by nuglet

You don't make billions being stupid.. But you can lose it by being senile and horny.

I'm not a billionaire (give me a couple more years), but I'd like to think I'm no fool either, and I'll be the first to admit that some women have made me say and do stupid shit. Some of it makes me cringe, some I don't regret. As long as those guys don't have any regrets, sure, go for it. But I'm still wondering what exactly Hef gets out of it. And I sure as heck don't see what that billionaire saw in Anna Nicole Smith.

You guys have already nailed it. Hef gets all the play he wants, has been getting it pretty much as long as he's been an adult.

If I remember my Playboy history correctly, this would only be the third time he's getting married. All that pussy, all those women, and only the third time. Makes you wonder.

On top of that, you have to consider that when you've got his money, the business run by others, no other worries, wouldn't you want to be a kid again?

When two people genuinely connect, age doesn't seem to matter. Outside the obviously inappropriate relationship with a minor child, I'm a firm believer that two consenting adults should be able to make adult decisions about their relationships, and in a perfect world, not catch any judgment for those decisions.

But we don't live in a perfect world. True, the lady in her late 20's dating a gentleman in his mid-late 40's really doesn't have much to worry about as far as societal judgments go. I'm fairly certain that young lady's biggest concern would be her parents' reaction, and once that is no longer an issue, then everything else should fall into place.

An older gentleman dating someone under 21 may have more difficulty if he likes to frequent bars or adult establishments, simply because his lady friend can't always join him. But I'm sure that two people who care about each other can find other enjoyable activities, like movies, day trips, cooking dinner at home, etc. that are also more likely to strengthen the bond between them.

Of course, maturity and life experience are both very important on both sides of a May-December relationship. I've dated plenty of "men" in my age range who turned out to be as selfish and immature as teenage boys. It's no wonder I'm attracted to "older" men. (For the record, my two biggest celebrity crushes are Jon Stewart and Anthony Bourdain. Those silver-haired, silver-tongued devils steal my heart every time they pop up on my television screen.)

And I have to agree with Rand Al'Thor. Hef has easy access to some of the sexiest women in the nation, and he's not a stupid man. If he felt the urge to marry this woman instead of keeping her as a mistress or a girlfriend like most of the others, then there must be some real feelings between them. Bravo, Hef.

What Wilson said lol but no I've dabbled/date outside of "working" with men up to very late 40's, it helps when there not acting like old men, they like to go places and are funny, high sex drive etc. I'm a mix of a young and old "soul" so basically he has to be also in a nutshell. Even if he is older than late 40's genuine attraction is big for me for it to be a truly manageable relationship I've never been attracted to men over like 55 or so. So if they older than that it'd probably be only for the money unless he has a beyond incredible personality but that's still not quite enough for me I have to at least kind of like looking at you lol.