George Clooney vacations with Cindy Crawford & Stacy Keibler in Cabo yet again

Last night, I read a Daily Mail story about George Clooney traveling down to Cabo san Lucas yet again, for his millionth Mexican holiday of the year. First: when did Clooney become of the male version of Jennifer Aniston? Second: At first, the reports suggested that Clooney was flying solo in Cabo… meaning that Stacy Keibler was NOT traveling with him. But the Mail claimed that Cindy Crawford was there, so I got super-excited that Clooney might have dumped Stacy right before his big awards season push. Turns out, not so much. These are new photos of George and Stacy together in Cabo yesterday. You can see them riding in a golf cart together.

So… Stacy and George are still together. Oscar-Date Barbie will be Clooney’s Oscar Date, for better or for worse. But will she last much longer than the awards season? Elisabetta Canalis managed to stick around a lot longer than I was expecting, but then Eli messed it up by talking about marriage and babies and Clooney quickly had security escort her out. Stacy might fall into the same trap too – one look at her Twitter page, and it’s clear that she’s got love and babies on her mind. Poor Cray-Cray. At least she’s making money out of this relationship though – the NYDN just re-confirmed that Keibler’s appearance fee has jumped to $25,000 a gig, and that she’s in high demand now that she’s Clooney’s Girl.

I’m also including a photo of Cindy Crawford, the girl Clooney wishes he was with.

Photos courtesy of Fame.

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49 Responses to “George Clooney vacations with Cindy Crawford & Stacy Keibler in Cabo yet again”

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  1. Bite me says:

    This is all perfectly normal… Um where is Cindy husband

  2. k says:

    Clooney is not aging well.

  3. guest says:

    Well you gave Stacy what she wants more publicity. Now we are going to see Stacy around Cabo for the next two weeks. Boring…

    I did notice that she does not tweet cryptic messages about George the last two weeks. I think if she wants to be Oscar Barbie she is going to tame the comments. He has her on a tighter leash. I bet stacy is dying to tweet about her love, but can’t. She may last for awhile ,but eventually she will want more and he won’t provide what she wants.

  4. Eve says:

    He’s not aging well…that second thumbnail: it looks like his cheeks are sliding off.

  5. inception fan says:

    By the way, did you know that a few years ago she tried to hook-up with Leo Dicaprio? photo proof
    http://www.bellazon.com
    /main/index.php?showtopic=1405&st=12080

  6. Marjalane says:

    Stacy Kiebler ALWAYS has a smug little smile on her face, and seems to be very aware of where the camera is positioned. I’m a lot more envious of the weather in Cabo, than of her relationship with Clooney.

  7. constance says:

    Meh. These are people that never leave the all inclusive resorts they pay to sit around in. That hotel and resort could be anywhere, I’m sure.

    • constance says:

      I agree. When I go to a location to vacation, it is because I want to explore the whole region! Not sit on the same beach I could sit on behind my mansion back in California.

  8. Kali says:

    This “relationship” makes me just scratch my head and go huh?

  9. Intercontinental says:

    Umm… These look very much like the last lot of pics..or, have we seen that many they’re all rolling into one..?? Either way the showmance is boring…

    @Kaiser: comment on her twitter page made us laugh but, for those of us who don’t follow twitter we know what’s on there because of GC’s reinforced denials on marriage and babies which have not been forced by gossip columns recently as far as we can see! No, she really isn’t the brightest button in the box is she…hhmm…very sad actually…

  10. madpoe says:

    I heard some saying from someone I don’t recall, but they said something like “Vacation is for people who hate their jobs”

    On the other hand, I’m guessing the MO for Clooney is to spoil this woman so rotten that she’ll slip up and beg for kids and the ring and he’ll dump her b/c the stars he helped put in her eyes got too big.

  11. Kara Ann says:

    I really, really hope that we don’t get constant photos of them. Seeing pictures of Elisabetta Canalis’ naked *ss during their vacations really got on my nerves.

  12. dorothy says:

    Clooney on vacation with another one of his beards.

  13. Jenny says:

    Why does he never take his women somewhere alone, just the two of them. It’s like he needs a chaparone with Cindy and her husband. Kind of weird. His vacations are beginning to blend.

    Are their families coming later as I recall her saying they were spending the holidays together. But as awards season heats up, her oversharing will probably decrease–don’t want anything embarassing.

  14. T.C. says:

    Look it’s grandpaw with his tall, leggy granddaughter…oops I mean Clooney and his new piece. The man is looking more pathetic everyday next to Stacy. Someone should really tell him that she makes him look OLD.

  15. Lady LaLa says:

    Cindy still walks like a Model, even on the beach, lol

  16. Suze says:

    He looks like hell. Maybe he is battling chronic pain and health issues – he sure looks like it.

  17. Rita says:

    @Kaiser

    So what is this close relationship George has with Cindy Crawford. I don’t see anything wrong with it but what’s the history. Can anyone dish?

    • atorontogal says:

      I’ve always thought George has a thing for Cindy. I could be wrong but it’s just weird he spends ALL his holidays (no matter with which flavour of the month) in Cabo with Cindy and family.

    • spinner says:

      George has a thing for Cindy’s husband…Randy Gerber. George & Randy get it on & they also have the luxury of watching Cindy work it out with George’s latest beard.

  18. spinner says:

    I have a condo in Cabo & try to make it down a few times a year. It is a wonderful get-away with a charm all it’s own. It is a short flight from LA which is a definite plus for the Hollywood crowd. I can definitely understand why people visit Cabo again & again.

  19. LeaR says:

    “I’m also including a photo of Cindy Crawford, the girl Clooney wishes he was with.”

    Cindy Crawford is:

    a) In her 40s
    b) apparently pretty bright – she was on scholarship studying chemical engineering before turning to modeling full-time
    c) extremely successful career-wise

    No, Clooney doesn’t wish he was with that. Crawford’s intelligent, not-desperate-for-a-famous-man’s-scraps vibe is like a bucket of cold water on his boner.

    I would love to eavesdrop on Crawford’s convo with her husband when they dish on who Clooney is bringing around this year. You know they do it, if only to avoid embarrassing faux pas like “Oh Stacy, I made you a gin & tonic since I know you like them – oh wait….that was the girl from 2006….”

    • Alexis says:

      Disagree. If he’s not gay (a huge IF), he probably sort of wants do CC (not like he would, but that’s generally how hetero M-W friendships are). Maybe he’s not man enough to date a woman like her (after all, he doesn’t want to marry), so he goes for bimbos in their early-to-mid thirties.

      It is the character of the women that are the problem more than their ages. I really don’t think 32 and 50 would be that creepy if the woman was a mature, legit person — which his girls never seem to be.

      But if he were the serious-relationship kind…maybe CC’s what he’d go for.

  20. Oenix says:

    Rumour has it that Cindy and Randy are bi: Randy&Clooney; Cindy&Stacy. A “Menage a quatre” if you will…..

    • Snappyfish says:

      Clooney has always had a thing for Cindy. He has said it himself in an interview with Gerber (they are business partners in some club in Vegas) elisabetta looked a lot like Cindy. He bought implants for the one before her & the rumor was they were based on Cindy’s.

      As for Cindy & chemical engineering. She was at Northwestern which is a v v good school. However.she was only there for first semester freshman year so can’t say how much actual engineering study you do in 4 months. But kudos to her for getting into Northwestern

      Maybe the above poster is right & it’s all about Gerber & not Cindy as that would explain a great deal

  21. Oenix says:

    And a few “sandwiches” in between…

  22. Jayna says:

    No chemistry with Stacy for George. He always looks bored out of his mind with her.

  23. wunder says:

    They are swinging together for sure.

  24. LucyOriginal says:

    I never thought I would agree with this theory , but the more I see Clooney´s choices and vaca with friends (not his family)… the more I think they do swing.

  25. lara says:

    clooney on vacation is always surrounded but al least 30 friends complacent which i exploit it and profit from it we’ve never seen celebrating chrimas or thanksgiving with his parents or sister,could be around them because age,that our little man george!

  26. Hmmm says:

    I so agree with #5 comments! I guess when you’re self-absorbed, it’s all about you and the world that revolves around you. You’re more concerned about a sybaritic lifestyle, your tan and the sex and drink and being catered to than to actually explore the big, wide, wondrous world that is not in the least interested in you. Geez, all that money and no curiosity. What a waste!

  27. Playlist says:

    Cabo is like going to Mr. Chow or the Ivy Restaurant. Celebs go there to be seen, especially if they are trying to sell something to the media (a movie, a relationship, or in George’s case, both). They have plenty of money to go somewhere more private but they are not going there for privacy.

  28. Saph says:

    Stacy may not make it too the red carpet she wants so much. Already hearing rumors of a split and going by the latest pictures Grandpa Clooney can’t hide his disdain for her. He never looks at her and doesn’t seem to care less that she is around. Amazon Barbie went a little too far with he loves me tweets and it is hard not to notice she hasn’t tweeted anything for sometime. No more guess where I’m going, pictures of Georges dog and her letting the press know in advance where they will be together. Looking like the last days of the Italian Queen. George should grow a backbone and walk the red carpets with out the Amazon Barbie who makes him look like an old grandpa with his hot nurse. He would get more attention alone then with this fake over botoxed wannabe. No one is buying this showmance…..

  29. guest says:

    After about 48 hours of having a vacation together in their Cabo Bubble, what could these two possibly have in common or talk about, besides football, drinking and cleansing.

  30. lisa says:

    You would think Cindy/Randy would be tired of befriending all Georges’ girlfriends. Has to be strange. Do they ever slip and call the new on the old ones name. Gosh SMH

    But Stacy will be on Georges arm for Oscar. She will be wearing a great dress and the press will be all over them.. UNTIL.., the JPs show up he and she will be forgotten.

    Time will tell how long she and he stay together. She is way more talkative and visible then the ones before her.

    • shawn says:

      She’s no more talkative or visible than Canalis, except that Canalis did most of her yapping to the Italian press. I still say she’s gone by the end of the year, as I said on one of the blog entries about one of the premieres she went to. It would explain why she wore gowns to premieres that the other women wore cocktail dresses to. I also am starting to think that Clooney signed the contract with Keibler at the same time he signed the one with Canalis, and he was stuck with doing six months minimum with Keibler. I think he told her up front that all she was going to get was six months, and she didn’t care that’s all she was getting as she was happy to get any of the famewhoring opportunity.

  31. Nev says:

    yes cindy!!!

    top ten forever.

  32. Poppy says:

    Same ol’, same ol’, he has all the money and time in the world to visit amazing and unusual places for his holidays but he just does the same thing over and over, love life included. He really has turned into just a boring middle aged man.

  33. crtb says:

    Am I the only one who thinks that George isn’t having all the hot sex we think he’s having? He has really cronic pain and back problems. That is why he surrounds himself with PYT so that we will think he is having hot sex 24 hrs a day. When in fact they are tucking him in at night. The other one told us he was nothing but a father figure. She wasn’t joking!

  34. wunder says:

    Just saw ‘The Descendents’ last night.

    Was suprised at how ‘scrawny’ George looked. He really needs to hit the gym!

  35. Julie says:

    Where are her kids…Christmas vacation? I would hope they would be with their children instead of sex buds.