Hugh Hefner dating Jenna Bentley? 

Pacific Coast News is asking the question "Does Hef have a new girlfriend?" after Hugh Hefner has been seen lately getting close to model Jenna Bentley (here and here is what she looks like topless - NSFW). That's Hef and Jenna at the Playboy mansion earlier this month. For those of you wondering, Jenna's 21. Hef was 63 when she was born. Honestly, I don't see what the big deal is. I mean, it's not like he was 67. Jenna had already learned how to walk well before Hef turned 67. When I put it in those terms, it's not so "weird" anymore, is it? Hater.

*5 Hugh Hefner Jenna Bentley pictures total in the gallery:

  • Hugh Hefner Jenna Bentley Dating 1
  • Hugh Hefner Jenna Bentley Dating 2
  • Hugh Hefner Jenna Bentley Dating 3
  • Hugh Hefner Jenna Bentley Dating 4
  • Hugh Hefner Jenna Bentley Dating 5
STUFF YOU MAY HAVE MISSED:

[Pacific Coast News]
  • mark

    she is hot! damn lucky man!!

  • T

    To be honest I'd be WAY more surprised if he was with somebody his own age. It's really stopped being shocking. Still gross though.

  • The Brain

    Hugh looks like a drum major for a gay marching band!

  • Zarcastic

    It seems to me Hef is growing boobs or are they fake boobs? He's pathetic.

  • Dragon

    Luckiest man alive.

  • brit

    that girl looks way older than 21!! and beyond the surface of the skinny-tan-fake tits- bleached hair formula...she's not the most beautiful :/ hef can do better!

  • kjih-tv

    Um... that's great, but... uh... why do you have a picture of Charlie Sheen up there w/ one his bimbos?

    I swear... Charlie Sheen has rapidly detorirated into a 40-something Hef in the past 10 years. Anyone remember when he was strong, hunky and good look during 'Hot Shot!'? Whatever happened to those days?

  • Paul

    Charlie was a Navy Seal for many years. The physical and mental stress of many combat missions have taken their toll on him. It is tough being a fighting warrior.

  • Frank

    I want a pair of PJs just like that. Where can I buy them?

  • James

    Another blonde with fake boobs. Come on Hef. Switch it up once in a while.

  • Carlos

    I wish them the best.


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