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Holly And Hef Reunite For The First Time Since His Engagement

| Filed under: Love LinePlayboyPerezTVHolly MadisonReality TV

This is pretty hard to watch.

Holly Madison and Hef come face-to-face for the first time since he announced his engagement to Playmate Crystal Harris.

Holly visits the Playboy mansion during a segment for her E! show Holly's World where she makes uncomfortable small talk with Hef and then blurts out, "Congratulations on your engagement!"

Watch the very awkward exchange (above).

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34 comments to “Holly And Hef Reunite For The First Time Since His Engagement”

  1. 1

    Aww she loves him still and you can see hef loves her too - IT SHOULDVE BEEN HER

  2. 2

    holly is just mad because she not the one who going to get all his money. to be honest who would be in love with this old man. the only person who probably ever really loved him is his first wife. everybody else is just dating him for his money. who would be in love with the crept keeper?

  3. 3

    I don't believe Holly was engaged for real with Hef. I don't believe that Crystal is engaged for real with Hef either. It's all fake to sell magazines, dvds and reality shows.
    By the way, I think Hef's real love is his secretary Maria and I think Hef is a pretty generous person. I like him.

  4. 4

    It shows a not very articulate giggly girl trying to speak to her aging great grandfather??, while monkey humps purse? I sat through a commercial and you showed nothing of her confronting hef yawn lols

  5. 5

    ewww she wants that dead$$ thats whats up!

  6. 6


  7. 7

    Nice he got to use her like the gold-digging, spooch receptacle she is before moving on. Holly the wHore.

  8. 8

    AW you can you see the way they look at each other they still love eachother. I know she loved him a lot but he couldnt give her kids so she ditched which is kinda stupid if you ask me. why didnt she just adopt

  9. Wrenn says – reply to this


    She needs to move on and find someone her own age. The only reason any young woman would want Hef is because of his money. I know she wants kids and I would hope that she would want to find someone who is young enough to be around to raise them with her. Move on Holly!!!

  10. 10

    You can see the hurt in her eyes.

  11. 11

    she wishes she was marrying him instead

  12. 12

    She's really a lucky girl to have escaped!

  13. 13

    holly still loves hef and hev still loves holly you can see it in their eyes

  14. 14

    Canèt see the vid

  15. 15

    Really gooooooood heheehehe

  16. 16

    She has every right to be pissed.

  17. 17

    i think he's gonna die soon.

  18. sgold says – reply to this


    ew not my cup of tea, but whatever, not my life. I can tell she genuinely still has feelings for him and visa versa. just my opinion!

  19. 19

    Yeah, that sucks. We've all been there. Seeing the ex for the first time after a long time and not knowing what to say.

  20. 20

    I feel sad for her. I think she really loves him still.

  21. 21

    wow heff really loves her and I could say that holly really loves him for her body lenguage but is hard to believe a girl her age love a guy his age so I'm not sure what I just watched

  22. 22

    Awww… she misses his wallet. How whore-able for her.

  23. 23

    Very interesting how nobody mentions how shrivelled up Hef is looking. I kind of feel sorry for all of the bimbos that hang around at the mansion hoping to find a man who will pay for all of their cosmetic surgery. The whole Hef & playboy thing is vulgar and gross

  24. 24

    She clearly still has feelings for him. How sad to watch.

  25. 25

    hes a sad old man.. buying young women with his millions. if he was broke noone would touch him. sorry.

  26. 26

    A) Who cares. B) How the hell was Holly's World picked up for another season? That bitch is DAMN LUCKY she has Josh on that show to draw viewers because God knows she couldn't hold a viewer's attention for longer than a few seconds. Holly you have ZERO personality, hun. And the phony personality you do have is…well…phony. BOOOOORING! But YUM I do love me some Josh. I say fuck Holly and make it Josh's World!

  27. 27

    well that was depressing…

  28. 28

    I honestly believed she truly loved him. When I used to watch The Girls Next Door, you can see how much she loved him. All the other girls did it for a job (Bridget was my favorite though!) but Holly truly found love. Yes it is strange how old he is, but she always wanted to be with him and not go out with the girls. I think his fiance is marrying him for all the wrong reasons. Poor Holly, I can't believe it isn't her.

  29. 29

    in her eyes and his it kind of looks like they do miss eachother and still love eachother. who knows it could be just for cameras. but you gotta remember she lived with him for 7 yrs that's a long time to stay with someone so you know there's more to them then just the fame for tv. i can see why anyone would love hef tho he seems really traditional as in he treats the ladys good still opens doors ect. and he is generous all around and shares his many houses. supposedly his ex wife still lives in one of the houses next door also and has since they split up. if there's not some sort of hurt in her eyes shes a damn good actress. when i watch the kendra show you can always tell when shes acting lol even tho i still like her shes a bad actress lol. but i bet holly's just upset cause hef hasn't even been w/this crystal girl for that long. i would think too that crystal's only in it for the wrong reasons.

  30. 30

    Seriously, there's something wrong with your links or something. I can never see the videos that ae linked from external sites.

  31. 31

    oh please Hef is gay,can't believe people actually believe this rubbish!

  32. 32

    Everytime she looks at him you can tell she still loves him and that it is akward for her because she feels a little hurt.

  33. 33

    Re: kaitlyn_swing – Yeah, you're right. The people that say she's nothing more than a gold digger obviously have never seen the show. She was with him way before those E! cameras started rolling. And you could just tell by their body language that they were in love, especially her. Like you said, whenever the other girls would go out, she would either come back early, or not go at all. Nothing about their relationship was an act. Hell, when I was 18 and 19 I was in love with someone a lot older (not that old, though). But that guy didn't have money, and he's probably the guy I had loved the most. So you don't need money to have feelings for someone.

  34. 34

    awwww I actually found myself a bit choked up over this lol Maybe she really loved him after all? Up until this video, I figured she was just another wannabe-playboy-legacy-mrs-hefner-gold-digger. Now I feel bad for judging Holly! Shame on me! I guess they would have been a loving couple. This is sad :(