Hugh Hefner’s new squeeze to be (29 Photos)

  • Cringer

    Well she looks closer to his age than the previous ones.

    • party pooper

      well that's one ugly trophy wifed bimbo.
      I wouldn't touch her even with Mapa gloves.

      • Really?

        Why did you pick the chive to come out of the closet?

    • Jim Kelly

      Hope he makes her sign a prenup.

    • Yep

      I saw an interview with Heff once. He said "When I die, I want to come back as me!"

      GD right Heff…

    • Static

      there is no way in hell that girl is 26. lmao.. more like 46.

      • whale huntr

        Maybe she is 26 Lindsay Lohan years…….

    • Silverstone

      Yeah…50 years closer instead of 55!

  • Adz

    nice to know there is a bit of consistency

  • Lia

    An 80+ year old is getting hotter chicks than most men will in their lifetime

    • The Drunk IT Guy

      I fall into that 'most men' category.

    • what

      I wonder if having a shit ton of money has anything to do with his attractiveness to the young gold… I mean ladies

    • jjjjjjjj


    • judson

      An 80+ is the understatement of the year…

      • NoodlumNad

        its either the fact that he probably has money money than he could spend in 3 lifetimes or he's hung like a horse.

    • TommyKnockers

      yeah 80 year old billionaires have this amazing ability to become super attractive, it's a scientific fact.

  • The Drunk IT Guy

    How he does it I will never know. Proper LAD.

    • GoldDigga

      One word. MONEY

      • Meme

        Also Viagra

        • Pretty Smile

          And a couple Popsicle sticks…..

      • Nishtai

        I think that besides money, he had vision. He's been humping hotties since he started Playboy in 51, at least. He was 30-ish then. And no money. No BIG money, anyway. He's the ultimate example of how you can succeed if you put your mind to it… And how you can still bang chicks that'd give most 40 year-olds a heart attack at his advanced age.
        Chapeau, Heff

  • Yazo

    # 1 Look! He just muffed her.

  • Tiber_Septim

    Second time around, should be a winner

  • Not me

    No way in hell she is 26

    • gclark

      A few of those pics look like shes late 20's early 30's

      #2 her hand looks aged


      mid to late 30s id bet

    • Gabe

      I agree… those are some hard city miles

  • passwordistaco

    At least she's hot. Before you say "of course she's hot" remember the 3 bimbos from that awful tv show, 2 were hideous and I don't think he was banging the 3rd.

    • ImpressMe

      Every one of them was hotter than this heifer. Shes got some serious manface going on. Great body..but…no thank you.

      • Concerned Chiver

        You both are bitter idiots.

  • N2MotoX

    #8 I'd hop on that bunny!

  • Guest

    She isn't even that hot. I'd imagine she's a horrible person.

    • Parasite

      I hope he makes her suck his old balls and then dumps her trashy ass at the alter out of spite. You know she's just missing some spotlight and sugar daddy support, and you know he has an iron-clad prenup – particularly after her last episode.

      Sometimes in these April-December deals I think the guys are taking advantage, but this skank seems like a parasite.

      • Dez

        I heard her on Howard Stern after she left him before the first wedding. She was talking shit about him and the lifestyle he provided for her. Fuck that ungrateful gold digging skank. I'm hoping Hef snaps out of it and shitcans her.

  • ViagraForBreakfast

    hope there'll be a leaked sextape..

    • BobbieJimmy

      I was gonna write that u r a perv if u wanna see that old guy naked.
      but then I read your name, and i lolled.

      well played sir

  • hotrippr

    Meh, he can do better.

  • iaDF!

    Weren't they supposed to get married before, and she backed out last minute ?

    • Guest

      You read good!

  • gclark

    I smell a unexpected death soon and an extremely rich mistress.

    • C2tha3


    • DeputyDandy

      He's 86…….wouldn't call that unexpected.

  • @onebigkelevra

    I hope she knows how to do CPR….

  • Eric

    "Give me your hand while we cross the street, grampy. I mean, oops"

  • That Guy

    The whole vampire thing in the first 10 photos or so, seems a bit fitting for her. Although, I imagine it is mutually beneficial, he gets to play with a kid and she gets money.

  • seabath

    He's not even smiling in half of these pictures. Does he know what's going on anymore?

    • incontanance

      Probably not…but that is one hot nursemaid.

  • BigManJones

    Age old question: How much old man penis will you touch for lots of money?

    • John

      A whole lot of penis

    • Guest

      Seven! Wait, what?

    • Realist

      She probably won't have to touch much. He is so old that I doubt Hugh can remember where it is, or what it is for.

  • csor1120

    #25 It's nice to see a couple together that is truly in love, errrr, she loves his money

  • The Dude

    Now I ain't sayin she's a gold digger but……… Aw fuck it, I'm just jealous. Rock on Heff.

    • Yep

      I said this earlier but it's worth repeating:

      I saw an interview with Heff once. He said "When I die, I want to come back as me!"

      I want to come back as him too!

  • Dr. Beardface

    Its good to see some people are still really close with their grand parents like this young girl with her grandpa.

  • K-1

    #2: This is also how she got the position in the first place!

  • TheGnome

    Dont do it Hef. Holly was way more loyal than this whore.

    • Uncle Dirty

      And way hotter than this chick, too. This chick's face would scare a horse.

  • HughGoFirst

    #22 You think the son ever gets sloppy seconds?

    • Guest

      That just made me throw up in my mouth a little…

    • Silverstone

      Yes…and thirds, and fourths, and fifths, and,,,,

    • Silverstone

      Those girls probably prefer Junior…he doesn't need Viagra!

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