Jennifer Aniston is on vacation in Mexico with Will Speck: boyfriend rollout time?

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One of the weirdest things about my job is that I sometimes have to consult a map to piece together a gossip story. For what it’s worth, through my brief geographic investigation, I feel like I can say that Brad Pitt and Jennifer Aniston were not on vacation together for New Year’s. Maybe. Brad was in Puerto Vallarta for several days after Christmas, and we know that because there were photos of him leaving Puerto Vallarta. And now there are photos of Jennifer Aniston in a resort in Tulum, Mexico. Tulum and Puerto Vallarta are on opposite sides of the country. So… no, Brad & Jen were probably not having a hot holiday hookup, even though that would be the tabloids’ wet dream. Instead, it looks like Jennifer is very casually rolling out a relationship with a director named Will Speck? You can see the photos at the Mail:

The DM doesn’t have anything other than the photos – Jennifer wore a black bikini and she was seen hanging out with Will Speck, but they were there with a bigger group of people, including Jimmy Kimmel and Jason Bateman and their wives. That whole group is very close. Speck directed Aniston in Office Christmas Party and The Switch, and apparently they’ve been seen out and about – often in a larger group – before. The DM says Aniston and Speck are “just friends” but apparently there’s gossip that they have a “very special connection and he’s definitely a candidate to be more than just a friend at this point. He’s witty, compassionate, sensitive and has a real sense of adventure and ambition, which ticks a lot of boxes in what Jen’s looking for in a guy.” He’s 50 years old (same as Jen) and he doesn’t seem to be married or in any kind of long-term relationship.

Methinks that Jen and Will have probably been happening for a while and she’s starting his boyfriend rollout now. Which is funny, because everyone around her probably wants her to play into the “Brad and Jen are going to be together at the Golden Globes” story.

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Photos courtesy of Getty.

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83 Responses to “Jennifer Aniston is on vacation in Mexico with Will Speck: boyfriend rollout time?”

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  1. Sierra says:

    He could be a nice man but he has a frat bro douche face 🤷‍♀️

    I will never understand people who spend Christmas & New Years with friends instead of family members. I love my friends but I don’t spend important holidays with them.

    But then again, not many people are lucky enough to have wonderful family members like me so they might see their friends as family.

    • Sa says:

      “I will never understand people who spend Christmas & New Years with friends instead of family members. I love my friends but I don’t spend important holidays with them.”

      And I always think how wonderful it is for people to have such close friends that they want to spend the holidays with them.

      Not everybody has family and not everybody has relatives they are close with. If you can make your own family that’s really special.

    • Audrey says:

      Why not both? I love my family and made time for them, but then 9am on Christmas Day I was off to Mexico with friends! I’m happy to have friends I am close enough to spend 5 days with AND family that is cool about me sharing my time.

      • sassbr says:

        Because some people don’t have amazing relationships with their family. I don’t spend the holidays with my family because I want to enjoy the holidays and they can be pretty toxic.

    • Harla says:

      Not a very nice thing to say about this man’s face/looks. But you are very lucky that you have such a wonderful family, appreciate them because you’ve got it better than most.

      • Sierra says:

        Believe me, I appreciate and thank God every day for having a loving family.

        The more I read about people who talk about horrible family members, the more grateful I am for my family.

    • Chaine says:

      Lucky you to have a decent family. Mine is toxic and Christmas is absolutely the worst. I would rather spend my vacation time relaxing with people I like and care about than subjecting myself to religious nutjob trumpster misery.

    • subber says:

      Past the age of about 14, many people do a Christmas/New Year’s split – Christmas with family and New Year’s with friends. And there are those who don’t celebrate at all, and “important holidays” aren’t important for everyone. Everyone has different traditions. None are weird.

    • lucy2 says:

      I’m very lucky to have a wonderful family too, and we do spend holidays together, but so many people I know don’t have that.
      Going away to a fun vacation with a bunch of friends sounds great too, especially if it’s a group that enjoys vacationing together.

    • MC2 says:

      He’s adorable & the world does not need each of us to “understand” why everyone does what they do when it’s different from what we do. We all have different lives, experiences & choices, but there’s no need to be judgemental when you don’t understand.

      JA’s mom was a narcissist & was not kind to her, so I applaud her for figuring out that friends were the people who were going to love & support her through her life. She’s lucky to have them.

    • Embee says:

      He has my ex’s eyebrows so I felt instant (biased) hatred lol.

    • Liz says:

      I’m seriously laughing right now, Sierra. What a weird and judgey humble-brag. I have an amazing given family, and I have spent MANY holidays with my chosen family instead. What on Earth made you type that comment?! Yeesh.

      • Riley says:

        + 1 Liz Such an ignorant statement. Who cares what she “understands”?

      • Sierra says:

        @Riley: obviously YOU care since you not only read my comment but also wrote a reply.

        As for being judgmental, sweety, how about looking into a mirror? You judge me for being judgemental? Hypocrite much?

      • Cakes says:

        Clearly, she doesn’t like JA and was looking for something in this article to put her down about.

        That being said, my friends ARE my family, and I feel very grateful for that.

    • Riley says:

      Is your family as judgemental as you?

      • Riley says:

        @Sierra— I do care when people are ignorant and arrogant. Obviously, if you read through the other comments I’m not the only one who took issue with your ignorance. You sound like you’re 12.

      • Cheryl says:

        Just the mere mention of JA will get some of these commenters instantly frothing at the mouth, and will desperately hold onto the narrative that she’s still some kind of barren lonely spinster hag with nobody to love her. It’s very strange indeed.

      • Aubrey. says:

        Lol she is 50 years old
        Why the hell would she spend NYE with her family when she has tons of friends and can travel.
        I highly doubt you would make this comment if it was anyone else with their friends lol.
        Transparent much?

  2. Lisa says:

    Non-story. He‘s gay and is married (to a man obviously). They have a daughter. His husband and their daughter were also in Tulum.

  3. Eliza_ says:

    There’s stories about how Brad and Jen will be seated “just feet” from each other at the Globes which is weird as Jennifer will be in TV area table. But I think this was thrown out there pre-Globes for keeping the triangle story alive… for the ‘will they ever find their way back to their lobster’ shippers out there. Not even a tv show can sustain the will-they-wont-they for this many years, it’s really a brilliant work to watch in PR at this point.

    • Michelle says:

      Golden Globes are all about ratings, so they will definitely put Aniston next to Pitt & not with the tv people at the back.

    • Kebbie says:

      The Morning Show cast is full of movie stars, so they’re not going to be seated like a typical tv show. Big Little Lies cast was in front of movie tables when they were nominated. I think it’s a sure bet that Jennifer Aniston and Reese Witherspoon will have prime seating. Don’t know that they’ll be “just feet” from Brad Pitt, but they won’t be in the back.

  4. boredblond says:

    I think he looks like Charlie Sheen.

  5. sarphati says:

    I used to hate the holidays. Mother in a mental hospital. Sibling living in another country. And one day, a kind Dutchman offered to host Christmas for me in Amsterdam and he did. Elegant dinners, fireworks at midnight, just an amazing time! Christmas dinner 24 years later. A few empty seats, a smaller group. But to this American, these folks ARE my family!

  6. lucia says:

    That man is wearing a wedding ring, so he’s obviously just part of her friend group. This is probably his husband

  7. Busyann says:

    I really like Jen, and always have. Her performance in The Morning Show was great, and she’s really seemed to find some type of peace the past few years. But, sometimes I wonder if she veers into Tom Cruise contractual relationships territory. Her relationship with Justin was bizarre and seemed more of a business type relationship than anything. Now I wonder about this one.

    • ann lawless says:

      Jennifer has a lot of gay friends that should tell you a lot about Jennifer. I think a lot of Jennifer male relationships are covers or business relationship i have worked with Jen she is not as straight as she wants everyone to believe.

  8. Annie Oakley says:

    Will and his family (Including his husband) go on the Mexico Christmas trip every year. He and Aniston and Jason Bateman go way back, Will directed the Switch Starting both of them. He’s still good friends Justin Theroux, too.

  9. Sarah says:

    Impressed by the detective work of my fellow Celebitches!! You could all do investigative journalism for a living, and maybe the United States and the rest of the world wouldn’t find itself in such a dire situation.
    Anyway, back on the Jen topic… I realy don’t get why so many people who proclaim to like her want her to reunite with Pitt. Like whyyy, howww? I don’t even like Aniston who I find highly overrated as an actress and who oscillates between lukewarm and awful as a human being (see Handler, Chelsea) but even I don’t wish Pitt and his many issue on her.

    • Esme says:

      I think (some) people are keen to see Jen with *somebody* – anybody, really. They try to pair her with a gay married man here, they try to pair her with recycled washed up Pitt (I’m loving the old pics, to be honest), they’ll have some other guy cast in the role soon… It’s like some part of society/tabloids cannot conceive of a single woman bring happy and fulfilled on her own.

    • lucy2 says:

      Seems like this should have been a non story if all that info is out there.
      It must be so weird to be one of those celebrities who is “dating” anyone they happen to spend time with.

    • Bookworm says:

      Because it will be salacious and sell stories, which is more important than the truth in the gossip world.

      It seems like she likes people to get along with each other and including Brad at a couple of large parties is probably no more than a friendly gesture.

    • Kebbie says:

      I think the people who want her with Brad see Brad as a good guy who fell under the spell of an awful woman. They don’t see him as a jerk who cheated, left her, then messed up so bad that he’s now estranged from three of his children.

    • Carol says:

      I don’t know anyone who likes Jen that wants her to get back together with Brad. In fact, they don’t care who she’s dating or if she dates. Neither do I. So this story is cracking me up!

  10. AppleTartin says:

    I wonder what went down between Jen and Chelsea. Did Jen finally wake up and realize her bestie was really a sycophant? Or did Chelsea do something like hit on Justin? Chelsea and Whitney Cummings were close too now they never mention each other.

    • Sarah says:

      For my part, I wonder what kind human being could be friend with a proud racist like Chelsea H. I mean, she did call a black little girl a monkey and said she couldn’t be racist because she has sex with black people.

    • crogirl says:

      Nothing went down between them. Chelsea was at her birthday party and also the pre Christmas one. She was also one of the first people Jennifer followed on instagram, so she is obviously still into racists.

  11. JanetFerber says:

    Yes, non-story. Jen looks good–perhaps a face lift for the new year and a toned, thinner body. She’s a hard worker and is always doing a new project. I wish I could find her talented, but I do not. Nothing against her. In the whole Friends lot, I think the blonde woman (forgot her name) was the most talented comedian. I’ve seen her in other parts and she’s very good. But I guess Jen knows how to play the game better.

    • minx says:

      Agree with all of this. I find her very average in looks, talent, personality—she’s not an interesting person at all. But she’s doing something right, obviously.

      • tempest prognosticator says:

        I don’t get it, either. Aniston is the epitome of mediocrity. There is nothing wrong with that, it certainly seems to appeal to the masses. The only time it annoys me is when mediocrity is celebrated and rewarded for being something it isn’t.

    • Jadedone says:

      Whenever there is an article about JA there are always a few comments about her being “average” but she obviously has something interesting otherwise people wouldn’t waste their time commenting.

      • minx says:

        I don’t think so. That would mean we would only be commenting on posts about celebrities we like.

      • Aubrey. says:

        Lol it’s always the same comments over and over .
        We heard you this 1st 600 times.
        She is bland,but the women has people so incredibly pressed that she must be doing something right

    • Lena says:

      People really love her and she seems to have tons of friends, real friends that have stuck together for years. She has stayed friends with her ex’ husbands. And that is impressive to me.

  12. clatie says:

    Will Speck is an out and proud gay man. This is hilarious.

  13. L4frimaire says:

    Well this is a non- story if they’re just friends and he has a husband. The wedding ring is very obvious. As for everyone wanting to put Jen back with Brad, why? That’s so mean! Why would she want to be with her cheating ex-husband who has a bunch of kids he fights with Angelina Jolie over. Jen is having her moment right now and Brad is baggage. Surprised she doesn’t have a billionaire tech trophy boyfriend yet.

    • Sarah says:

      People are wondering because of the PR game that Brad and Jen are playing. It’s not just the media this time.

  14. olala says:

    I like her very much. Also applaud her that afrer all sge went through with her mother etc she to create a great life for her with real friends who love her.
    Regarding her talent i don’t know why so many “mediocre” statements in here. I find her very watchable and really giid in comedies. She was brilliant hillarious in Along came Polly. And she was fantastic in Good Girl with critical acclaim. I loved her in friends too. She knows what she can play doesn’t aspire for an Oscar for dramatic roles either

    • Sierra says:

      You obviously missed her desperate Oscar campaign for Cake.

      • IntheKnow says:

        @sierra, aren’t you just a nasty piece of work. It’s a new year. Get some perspective and rid yourself of that toxic internal poison.

      • Riley says:

        HaHa Sierra, did JA steal your boyfriend or girlfriend? You have some serious issues, in addition to sounding like a 12 year old. Go to bed!

      • Sierra says:

        Oh dear, I think I got myself some offended (dare I say crazy) JA fans.

        Pointing out that Jennifer does want that Oscar isn’t nasty or poisonous.

        What’s with you JA fans claiming that people aren’t allowed to criticise your goddess? This is a gossip side and we are allowed to write our opinions.

        I see tons of other true nasty and horrible comments on here and other posts but I don’t see you saying anything to them.

        Now try and get rid of your poisonous hypocrisy and judgemental feelings for the new year.

      • Aysla says:

        I finally watched ‘Cake’ last year, and I actually thought she was great in it. She really stretched herself. I was hoping we would see more of that– not necessarily tragedies or heavy dramas– but she slid right back into the familiar Adam Sandler comedy territory, which is disappointing (those movies are AWFUL). I did hear that she’s the best thing about The Morning Show, though. Might eventually get around to that.

      • Ann says:

        I remember when she was campaining for her Oscar, and even Jen got raked over the coals for brinning up “the dead guy”. It was young love, and they went their sepoerate ways, and she brought him up all these years later saying “he could have been the one”. Meanwhile, his wife and children were freshly grieving his death when she hit the press with this, and the man’s family was not very pleased about it. I thought it was pretty low of her to do that.

      • norah says:

        i never forgot that. she acted better for the nomination than in the movie

    • Ann says:

      All these interviews with her for all these years, and when she was up for an Oscar, she was suddenly telling the tabloids she was terrified of going underwater, because she had to for the movie. Geesh! She should have got an award for all her PR stunts.

  15. SJR says:

    I dunno, personally I had a rough 2019, and I honestly do not care a bit about who/if JA has a new boyfriend to roll out for PR.

    I watched that hot mess on Netflix w/JA and Adam Sandler. Awful. Both of them should be donating 90% of their salaries to charity just because the dreck they are churning out is so, so bad.

    • Say what says:

      ROTFL. And their PR agents had the audacity to throw to the media that it was the most watch show in Netflix History 🤣🤣🤣. Her and Pitts PR did earn their massive paychecks this summer!
      We don’t dislike JA we just see straight through that facade. The everybody’s friend. Who befriends their ex husbands ex girlfriends and invites them to her parties? She does. She wants you to believe everyone just loves her and she wants everyone to like her. Ya know the popular girl in high school type. Lol You would think after all the coddling Oprah and Ellen did to push that sympathy role on housewives she should be able to lure them to the movies and buy tickets instead of watching rom coms on streaming services. Yes that was a dig!

      • Sierra says:

        Be careful, JAs crazy fans will come after you and call you names and claim you are poisonous and a child just because you wrote negative things about their idol.

      • Ladygyms says:

        Hahaha, yeah must be that or maybe it is that there is nothing between her and Brad. But I guess Angelina did not want bacon when she keeps stealing women’s boyfriends to make women look bad for dating men. Justice has been served good for saint Angelina for being treated like shit by Brad since she is a know it all and it ok to target other women hypocrite nutcase buffoon. Everyone knows she is mad judge person do not like Jennifer Aniston but for this I say team Jen clowns illiterates

  16. Lensblury says:

    I’m not trying to be childish, just putting a random piece of useless info out there: Will Speck means “(I) want bacon” in German.

    Edit: while I’m at it – my two favorite literal translations of German words are “grief bacon” (Kummerspeck, the belly fat you gain from emotional overeating), and “damage joy” (Schadenfreude, malicious glee).

  17. vegasschmegas says:

    Holy Combover, Batman!

  18. GLOWBUG says:

    JA seems to go years between serious relationships. She had casual flings with Vince Vaughn, some model dude, maybe Gerard Butler, and then was more serious with Mayer and Theroux it seems like.
    Seems like the relationship has to be more than casual if she holidays with them so this would fit that but for the fact (I’ve read your excellent detective work upthread ) that’s he’s gay.
    I’m guessing she won’t have a New partner rollout until 2021 at the earliest. She just doesn’t seem to need to be in a relationship to be happy.