Jennifer Aniston parties with Chelsea Handler in Cabo

101125f1_aniston_b-gr_16

Over the holidays, Jennifer Aniston and several of her friends flew down to Cabo, of course. One of those friends was Chelsea Handler – whom Aniston has claimed is not a close friend, although Chelsea Handler does obsessively maintain her “Team Aniston” status publicly, very often. And for that, Chelsea was rewarded with a trip to Cabo. Chelsea and Jennifer even did coordinating bikinis, although Aniston looked much better in her bikini, of course.

101125f1_aniston_b-gr_35

There was also something about Aniston possibly having some romantic interest in Cabo too – she was photographed with this dark haired guy, and at one point, it looks like they’re hugging…? But even in these telephoto pics, this dude is giving me “he’s a gay BFF” vibes. Seriously, the dude looks like Johnny Weir is Johnny let himself go. If this is Aniston’s new boyfriend, then she could do WAY better.

101125F1

101125F1

101125f1_aniston_b-gr_01

101125F1

101125f1_aniston_b-gr_18

101125f1_aniston_b-gr_34

101125f1_aniston_b-gr_37

101125F1

Photos courtesy of Bauer-Griffin.

You can follow any responses to this entry through the RSS 2.0 feed.

90 Responses to “Jennifer Aniston parties with Chelsea Handler in Cabo”

Comments are Closed

We close comments on older posts to fight comment spam.

  1. Kiska says:

    Jennifer’s body is frickin’ amazing!
    Chelsey not so much…

  2. aenflex says:

    he’s totally gay.

  3. YUCK says:

    Please! They are both sooo passe! Come on go have babies and get out of the limelight

  4. jinni says:

    He looks like a pale Javier Bardem too me.

  5. Jezi says:

    Jennifer Aniston’s body is sick. I’m so jealous….lol.

  6. mslewis says:

    You know something, I’ve been to Cabo and it’s not that great!! Sure, it has a great beach and that 5-star hotel they stay in is beautiful but, really!! One or two visits and there is no reason to go back. There are so many other small Mexican towns that have so much more character and so much more to do. Maybe it’s the beach!! Or maybe it’s just a nice familiar place to go for a long weekend. Kind of like people in Miami hopping down to the Bahamas for a weekend.

    Jennifer looks great in that bikini, as usual. Handler, not so much.

  7. Malin says:

    “Come on go have babies”

    Oh crap, when did time rewind? I didn’t realize we were suck in 1953.

  8. MissCramer says:

    Kaiser- you are one of my very favs, and celebitchy is the only website Iread religiously. It’s my guilty pleasure.

    That said- I really think you guys have got it wrong with Chelsea Handler. I’ve loved her for years- long before Chelsea Lately, I was a bog fan on her standup. I understand why you aren’t a fan but I really think you’ve read her and some of her schtick wrong. Just my opinion.

    Anyway, the reason I’m commenting- I think that guy in the pics is Chelseas book tour manager person. He’s been on the show against his will before and yes I think he’s gay.

    Also, Chelsea may have invited Aniston, she frequents Cabo often and regularly takes her staff and friends.

  9. Kaboom says:

    If he isn’t gay I’m Pablo Picasso.

  10. Cheyenne says:

    No, Kaiser, she can’t do way better. They all keep dumping her.

  11. Marjalane says:

    Chelsea’s been so nasty lately, I’ve kind of gone sour on her. Kind of makes me sour of JA by association. But that didn’t take much.

  12. Granger says:

    To each her own, of course — and while I can see the appeal in spending your entire vacation at a ridiculously priced resort, lying by the beach/pool all day with your friends, and eating amazing food, I still can’t imagine doing it year after year after year, sometimes two and three times a year. It would bore me to tears! I don’t think Aniston is a very adventurous person, to say the least.

  13. Jayna says:

    Jennifer has the perfect body. But I can see why Brad moved on. She does a few movies a year and goes to Mexican beach resorts year after year and tans tans tans.

  14. Liana says:

    I don’t see the problem in going to the same vacation spot. My husband and I go to Lake George several times a year. *shrugs*

  15. puliz says:

    I’m all for consistency but this chick does the same thing over and over again.

  16. Jeri says:

    Was this the “Girls Gone Wild” estate Anniston usually stays at?

  17. danielle says:

    Chelsea doesn’t look THAT bad, I just think that’s an unflattering suit. And anyone would look bad next to Aniston in a bikini.

  18. serena says:

    Yeah it give me gay vibes too!

  19. OtherChris says:

    When is all that tanning going to catch up with JA? She must have super-human skin because most women would looke like wrinkled leather by her age with all that sun.

  20. Susan says:

    @Danielle, you’re absolutely right. Nothing wrong with Chelsea’s figure, just the strapless top is terrible. I hate to think how much that suit cost, but she’d have done better for 1/10 the price at Old Navy.

  21. karina says:

    I think Handler actually looks better than Aniston in these shots: certainly much healthier. The bikini top is not the most flattering, but who’s to say Handler picked it out? could well be Aniston was all “matching suits!! here ya go” then you can’t change out of it, no matter how horrid you look in it. Kaiser: totally gay. I think Aniston just wants to be seen with a man, probably part of her ongoing ploy to get John back (or any other guy in her arms as a “look how hot i am” ploy)

  22. Mia says:

    When I saw mystery guy, I immediately thought Gay BFF. LOL.

    Chelsea didn’t bother me until she jumped on the Team Aniston train. Since then, she’s become unbearably smug and annoying.

  23. redlips says:

    I have three friends that have homes in Cabo and they go every chance they get. My family owns a home in Cayman, and before it was bought, we went ever chance we had……once you find a place you adore, what is wrong with going? Nothing!

    The guy in the photo’s is Handler’s “book” agent, and yes, he is gay. Jennifer looks great! Not sure what agency used a “telephoto” lens to capture these pics, however, I will lay money on the table that they were trespassing!

  24. heathen says:

    I don’t like Chelsea Handler — something about her just bugs me — but I don’t think she looks bad. As someone up thread said, the suit isn’t that flattering & her “paleness” in the suit doesn’t help, but her body is ok. Jennifer’s body looks great — she puts a lot of work into it & it shows.
    I would bet the farm that guy is gay.

  25. The Hamm is My Dream Man says:

    Seems gay to me too.

    I don’t see anything wrong with finding something you like and sticking to it. If I had an amazing experience every time I went to a certain place, I’d do it year after year. And my family have traditions and places we go year after year.

    karina: That ploy about Aniston wanting to be seen with another man doesn’t make any sense considering this man is gayer than the day is long.

  26. nnn says:

    I think there is nothing wrong with going to the same place but if i had her money, i would go to so many other more beautiful beaches….Praia Do paraiso in both Brasil and Algarve (soutern Portigal), Praia do Carvalho (Algarve too woth its thousands of beaches and caves…a european jewel), Sevilla and benidorm in Spain, natural and beautiful beaches of East southern Africa like in Moçambique or in those eastern african islands/indian ocean like in Madagascar or in the Seychelles which has the most beautiful beaches with super white sand.

    The mediterranean area in Corsica, in GREECE (my god, this country has so many beautiful islands with super beautoful beaches) !!! Even Turqkey, Tunisia, Romania who is becoming the new Ibizza. The traditional carabean places with Bahamas, Barbados, Saint Lucia, Virgin Island, Trinidad & Tobaggo, Saint Vincent…even central america with Venezuella….so many hot places around the world where you can mix sun, beaches and cultural experiences….

  27. Mia says:

    A poster on another site has identified mystery man as Jen’s manager’s brother, who is gay. Whew! That was a mouthful.

  28. gWest says:

    I am not a Chelsea regular follower, I’ve only watched a handful interviews of hers. The one with T.I. is an all time favorite, I’ve watched it like a hundred times. She and T.I were absolutely hilarious together.
    I agree Aniston should try and get more inventive with her vacations cause she sure can afford it. Someone must be a creature of routine.

  29. skibunny says:

    @karina: you’ve got to be kidding!

  30. di butler says:

    Vacationing in Mexico, looking great in a bikini, tons of money. I feel so, so sorry for this sad woman.

  31. caramia says:

    @Marjalane:
    I feel exactly the same way about Chelsea, she is nasty at times and I used to think she was so witty. sourness is off putting for a cable talk host with no talent
    JA is so busy playing the same friggin’ character in every movie, she bores me to death.

  32. jen says:

    @Kaboom #9-LOL!!

  33. Kiska says:

    @ Other Chris. Jennifer can thank her Greek ancestry for being able to tan and not turn into a wrinkled mess. She has gorgeous skin. I’d never be able to get away with tanning like she does.

  34. Kloops says:

    GBFF.

    I’m not fond of CH, I think she’s mean spirited and rarely funny. Knowing she hangs out with JA makes me question JA’s character. I know it shouldn’t, but the b*tchiness casts a shadow. But, I’ll give her props, her body is amazing. CH looks ok too for 45.

  35. Louise says:

    I used to like Chelsea but she has become vicious and hateful for the last year or so. I still believe that she and Jennifer have a business arrangement. On her show Jennifer used to be one of her biggest targets. Chelsea is someone’s date to one of her birthday parties all of the sudden she thinks Jennifer is the greatest person in the world. There’s nothing wrong with going to the same place every year but most people would mix it up once in a while. She goes to Cabo at least 3 times a year every year for at least 10 years. Once in a blue moon she will tagalong on Courtney cox’s vacation.

  36. Cyui says:

    Please stop talking about Aniston’s skin. You’d look like that too with airbrushing. You can go on tmz or ohnotheydidnt.com and see her dark sun spots and wrinkles. She looks like the OC housewives.

  37. Tess says:

    Agree, Marjalane and Caramia. Such maliciousness becomes unwatchable, sooner or later, for most people.

    And I agree that their friendship sheds a very unflattering light on Aniston, who I’ve never previously had strong feelings about, one way or the other.

    But Handler’s comments, especially about Sarah Palin, are really over the line and reveal a bitter, hate-filled heart. VERY unattractive.

    Also, Aniston’s body is fabulous, but I don’t believe for a second that she hasn’t had some boob work.

  38. Abby says:

    Did not read all the comments just a few

    Think Jen goes there because of privacy moreso than anything. She looks amazing and I think Chelsea looks good as well.

    Actually I love Chelsea, and I think their personalities probably would mesh well together.

    That guy is in no way romantically involved with Jen. No way IMO>

  39. Abby says:

    Actually more sad that Chelsea or Jennifer did not spend time with their families on this Holiday. Are they both that busy?

    Do they not have any?

  40. Mizz Tickles says:

    Charlie Sheen called, he wants his wig back!

  41. Hmmm says:

    I just realized that Jennifer Aniston seems to have no girlfriends she hangs out with regularly. No obvious female BFF.

  42. misschrissy83 says:

    @Hmmm- Ahhh Hello Courtney Cox!! They have been friends since ahh…FRIENDS!

    Anyway I love Chelsea and sometimes you gotta be a bitch but an opinionated woman is always called a bitch by people when a man states his opinion he’s called ballsy and funny i.e. Bill Maur

    Why do we care that JA goes to Cabo all the time? SO WHAT! People create these opinions about celebrities like they asked us for advice!

    Oh and that guy is queerer than a 3 dollar bill.

  43. ziggy says:

    great for them! hope they’re having fun!!

  44. Josephina says:

    Someone mentioned that she should try other exotic beaches—there are MANY. Jennifer is obviously comfortable going to the same beach, year after year. It is what it is. Ho hum.

    I would like to believe that Aniston was held at gunpoint to invite Chelsea along with her to vacay in Mexico. Hanging out with Chelsea is as good of a choice as dating John Mayer–twice.

    Relaxing on a beach is nice, but there never seems to be any pictures of her spending any family time during the holidays in recent years. At the end of the day, she is a single woman living her life.

  45. gg says:

    Please tell me Chelsea isn’t really dating that idjit 50p.

  46. Trippin says:

    That hat sucks! How shallow and sad that in your 40’s all you’re known for is having a good body and looking good in a bikini.

  47. Hannah says:

    Cabo is just a VERY short plane ride from
    LA. It seems to me it’s a place she goes to for 2-3 days of relaxation–not a full on vacation.

    To Hmmmm. Isn’t Courtney Cox her BFF?

  48. maxpurr9 says:

    gay

  49. mln says:

    Hmmm maybe Chelsea and Jen are doin’ it??? Why else would she be so psychotically Team Aniston (i.e. the racist rants against Maddox) BTW I would like them both alot more if that were the case rather than just a paid lackey of Huvane.

  50. poppy says:

    he’s not a main squeeze and chelsea needs to see the root doctor.
    who is doing her hair?

    fyi talking heads, if you are going to “appear” in public, vacation or not, please, if you are going to go fake blonde, please maintain the illusion.

    sorry if i’m repeating anyone else but the roots distracted me from your comments.

  51. Cruisin_Through says:

    So she likes Cabo, so what? Whether you like her or not, she works alot and probably just wants a few days of R&R. No harm in that. She’s grown and can afford it, so good for her I say!

  52. OPN says:

    The guy in the pics is Alex, Aleen (her manager’s brother). And yeah he is gay.

  53. trish says:

    She’s helping the mexicans out. That’s her idea of charity.

  54. CaramelKiss says:

    If I had $100 Mill as well my body would look like Jen’s. Damn, I need 2 win the lotto or get a date with Charlie Sheen.

  55. kiki says:

    cosign miss crammer~ we need female comedians who dont follow gender sterotypes shes a playa baby~~~

  56. kiki says:

    love chelsea ~ i agree miss crammer

  57. norma says:

    can’t she try anywhere else for a change? boring old fart. looks great though, which is understandable, as she doesn’t have much else to do with her spare time.

  58. Jazz says:

    Now these pictures are going to be all over the magazines next week as “Jen’s New Love Interest” – ugh!!

  59. Liana says:

    She goes to Cabo at least 3 times a year every year for at least 10 years. Once in a blue moon she will tagalong on Courtney cox’s vacation.
    ************

    So what? Not a big Aniston fan anymore, but why would anyone care where she goes for vacation? I’ll be heading up to the lake for my 4th time this year. Poor pitiful me.

  60. spinner says:

    I have a condo in Cabo & I absolutely love it there. As was stated above, it is such a short flight from Southern CA that it is the perfect get-away. That said…I think Jen has switched teams & is now batting for the home team. Oh well.

  61. Henriette says:

    Aniston has a fantastic body, a gigantic house, lots of friends, plenty of work (sure, it’s mediocre, but it certainly pays the bills and then some) and had Brad back when he was still hot. I don’t think that’s in the least bit pitiable or sad.

    Maybe she’ll remarry some day. Or not. Maybe she’ll adopt a kid. Or not. Does a woman need kids and a spouse to be happy, or “worth something” in our society? Maybe, but I certainly hope that’s changing. How about if a person is happy, not hurting anyone else (eg. stealing another woman’s husband!), giving a chunk of money to charity, we let them live in peace, without accusing them of being pathetic or worthless.

    Oh, and I don’t like Chelsea Handler at all, but not because she’s single and childless; because she’s a drunken biatch.

  62. Kim says:

    A woman doesn’t need kids nor does a woman have to mention she wants kids on every press tour. Just say kids are not on my radar like Renee Z does.I find it a tad odd that Jen spends holidays and Bdays with her friends rather than her family particularly since her parents have had health issues.I guess I’m biased because my mom passed away and I would have loved to spend Thansgiving with her.

  63. normades says:

    Cabo *yawn* . Yes, this is why Brad left her.

  64. coucou says:

    Uuuuh, i think Angelina had a lot more to do with Brad leaving than Cabo…

  65. Lulu says:

    Chelsea is horrible. I watched a small snip of E! and she was making fun of Maddox using this racist, fake Asian voice. She also says the word, retard, a lot. I guess she and Aniston can discuss their mutual insensitivity towards others together. They certainly share that trait. Birds of a feather. I think Jen is just as catty as Chelsea. She hides behind her fake image.

  66. Cheyenne says:

    @Lulu: It takes a total creep to make racist comments about somebody else’s kid. And this is what Aniston chooses for a friend? It speaks volumes.

  67. Ashley says:

    @ YUCK, I totally agree with you…at her age she should show off and be proud of her kids not her flat tummy.
    @Malin, dear,,, Men & women in their 40s have babies if it is not for a medical reason that they can’t have one. They did it in 1950s and they do it in 2010s and they will do it for the rest of the eternity….
    @Caramelkiss, you made me laugh so hard it hurst…

  68. mollination says:

    Her body is so incredible. My god.

    And how could there even be a shred of a shred of a doubt that he’s not gay!?!? Jesus, that must get annoying as a celeb that everyone you touch or talk to is your new love interest. I really hope that blind item about courtney cox and jennifer not being friends anymore isn’t true. It seems what with her recent seperation from David Arquette that she would be a perfect choice for cabo-mate. But yet she’s not there :/

  69. Liana says:

    I agree that Chelsea Handler is horrible. She’s not even funny, just nasty.

  70. Camille says:

    A couple of untalented butterfaces hanging out together. Wow. Neat. 🙄

  71. southerncheerleader says:

    Nick Cannon called said:

    “Chelsea Handler Is Angry, Ugly White Trash.”

    AGREE!!!!!

    Jen, please find less-racist friends. You’re too classy & pretty to hang w/that.

  72. Cheyenne says:

    @mollination: Maybe Cox has moved on to new friends. Or maybe she doesn’t want to hang out with Aniston if Handler is part of the package.

  73. mscabo says:

    mslewis, I have lived in Cabo for almost 10 years and love it here. There are so many incredible people that live here and we have always a lot of things to do from golf, water activities (scuba diving, snorkeling, etc.), tennis, fishing, great social life, art walks and so much more!!! Cabo offers incredible weather whenever you visit! Jennifer looks fantastic, I just saw her today.

  74. Carrie says:

    The issue that I have with Jennifer Aniston is that she presents herself in interviews as a woman who is desperate for marriage, children, etc. while she lives her life as a woman who is perfectly content with life the way it is.

    A woman doesn’t need a man or children to enjoy her life. I am a single, childless woman by choice and I enjoy my life quite a bit.

    The reason that the press persists in calling Jennifer “lonely and sad” is because that’s the narrative she gives them- she appeases the heartland by playing the “poor victim Jen, whose dreams of home and children was snatched by Angelina” when we all recognize that if she wanted a husband and children, she’d have a husband and children.

    The hypocrisy of it makes me dislike Aloneiston.

  75. Katherine Mac says:

    golf? water activities? scuba diving? snorkeling? tennis? fishing? art walks?

    Does anyone truly think Aniston does ANY of those things? Hell, I don’t think she even does etc?

    She drinks and sits around and gazes at her own belly button while gossiping about all those other people doing something useful with their time and money. She has turned out to be a huge waste of oxygen.

    Handler is trash. Didn’t your mothers tell you that you csn tell a lot about a person by the company they keep?

  76. truthzbetta says:

    Aniston’s rocking body almost makes up for her plastic generic face.

    Her body’s aging in reverse, and looking fit, beautiful and healthy, at least she’s kind of inspirational in that one area.

  77. puliz says:

    Jennifer does the same thing she can do in her mansion by her pool in Bev Hills. Sometimes you wonder why she has to go to Cabo numerous times to sit by the pool and drink margaritas. Eh is Mexico drug central? uh ok…we might be onto something now.

  78. Eve says:

    Handler is trash. Didn’t your mothers tell you that you csn tell a lot about a person by the company they keep?

    @ Katherine Mac:

    We have an old saying in Brazil that states something like “Tell me who your friends are (or who you hang out with) and I tell you who you are”. I think the similar quote in English would be “Birds of a feather flock together”.

    People are assuming that Chelsea handler, as horrible and racist as she is, would be the bad influence in that friendship. Consider that they may be of the same kind and that’s why they’re BFF now.

  79. Me11 says:

    I believe Jen’s new love interest is Chelsea Handler.

  80. Dana says:

    They are at The One and Only La Palmilla resort. Go check it out online. I’ve stayed there and it is fantastic. If I had the money I would also go back over and over.

  81. southerncheerleader says:

    * Katherine Mac *

    “YES” – My mom did tell me that; it is sooo true.

    I had an experience with a person whom I thought was noble, who hung out with a horrible person, and I thought why would “NOBLE” be skin tight with “HORRIBLE” ????

    Turns out “NOBLE” was 2wc as bad.
    BIRDS OF A FEATHER, DO FLOCK TOGETHER.

    Jen, (& Jen’s people), we aren’t blind!

  82. Mario says:

    Chelsea confuses being a bitch with being a comedian. She looks worn out and old and she should not wear a two piece swim suit in public ever again.

  83. Ashley says:

    @ Mario, I have had 2 kids many years ago and my tummy jiggles but I wear a bikini on the beach at the reasort, becuase I like it, and my husband likes to look at me wearing it. I know for a fact that my body is not like what it was 20 years ago and will never be, I am proud of having stratch marks that are a sing of my 2 pregnancies. I could have kept my perfect body(I was alwyas fit and not over weight) and not have children. I am not over weight now just the right weight for my age and am damn proud of it,,,and to tell you the truth, whoever thinks my body is ugly doesn’t have to look at it, it is a free country. Jeniffer’s body is many many times better then mine, so why shouldn’t she wear a bikini?? But my life is many many times more meaningful than hers,, I know this.

  84. Eve says:

    @ Ashley:

    I think you have a really valid point here, but Mario was actually referring to Chelsea Handler, not Aniston (comment # 83).

  85. southerncheerleader says:

    OMG – Chesire Handman was making fun of the kid, Maddox — this is just NOT acceptable.

    It’s one thing to go after Angie, but after a kid.

    Chesire has NO class. She’s just MEAN –‘Ole WRINKLY, mean girl, with NO jokes.

    For being ugly to children — KARMA!

  86. The Hamm is My Dream Man says:

    Ashley: “But my life is many many times more meaningful than hers,, I know this.”

    Wow really? Your life is more meaningful because you have children and a husband? Well gee, I feel sorry for all those women who never get married for whatever reason or the women who can’t have children and have those “meaningful” stretch marks.

    Your life is your life and her life is her life. Neither is more meaningful for ANY reason. It is rude and insensitive to assume your life has more meaning that someone else’s.

  87. Ashley says:

    @ The Hamm, thank you for your input. I never in a 1000 years wanted to be rude or hurtful to anyone here or outside here. I have many single men & women friends whom chose to be single and are living their own dream life. I read back then (the last year J was with Brad) that he wanted kids but she wanted to smoke grass and so on…I actually think if she was not ready or didn’t want kids she made the right choice by not having kids than having unwanted kids just to try to keep Brad happy. I still know my life is more meaningful than hers for many reasons, it really has nothing to do with having a husband or having kids,,ha ha ha,,please tell me that was a joke!!!

  88. Jennefer you have a beautiful body so keep up the good work with it,and keep rockin your star from above, sky is the limit

  89. chelsea bully says:

    Just caught Chelsea Lately. Her panel member, referring to a ‘date’ between Angelina Jolie’s FIVE YEAR OLD daughter Zahara and Justin Beiber, said ‘But isn’t Bieber in a committed relationship? Like mother like daughter I guess’. This pathetic grown woman makes nasty implications for a 5 year old girl, it really turns my stomach.

    With all the talk of cyber bullying and bullying in general, you’d think Chelsea would not take her personal issues with Angelina Jolie down to the kids. I promptly changed the channel and am done with Chelsea Handler.

    She had Sophia Bush on her show talking about bullying and not crossing the line… What an utter hypocrite – and I was a fan! I’ve slowly come to realize that Chelsea Handler is a bully and the worst kind. Done with her.