Ashton Kutcher asked Jennifer Aniston’s then-husband Pitt if he could ask her out (update)

Update: This story is old! My bad, the Graham Norton people posted it on YouTube last week with no context. Apparently this interview was conducted in 2011. So the fact that it doesn’t age well isn’t as much on Ashton. Sorry about that. Also now I know why he looks so hot.

Ashton Kutcher was on The Graham Norton show last week in 2011. I’m going by the clip on YouTube, so I didn’t see the whole thing and assume that he was promoting The Ranch on Netflix. (Is anyone watching that? I have heard no buzz about it.) He told a story I’m assuming he thought was funny about making a thousand dollar bet with his buddy back in high school that he would go out with Jennifer Aniston at some point. When he finally became famous and got the chance to meet Aniston she was married to Brad Pitt. So he asked Pitt first for some reason, because men own us, and Pitt was like “whatever man” and kept smoking up (I’m taking creative license with this story). When Kutcher asked Aniston she wisely said “no” though. Can you imagine?

I made a bet when I was in high school. You have to imagine I’m living on a farm in the middle of America, really having no chance of living a happy life. Sitting around a basement with my buddies making bets… I say [to my buddy] ‘I bet you $1,000 dollars that one day I will go on a date with Jennifer Aniston.’ I’m 17 years old, she’s like on my screen saver on my computer. Four or five years later I actually meet Jennifer Aniston. She’s married to Brad Pitt at the time. So I went to Brad Pitt and I asked him permission to ask his wife out.

I said ‘Listen I made this bet with my buddy. You’re a cool guy, you’re going to let this go down, right?’

He looks at me and he’s like ‘You go for it.’

So I asked her and she turned me down. She’s like ‘That’s not a good idea. No.’

Ashton Kutcher has blocked both Kaiser and me on Twitter so he’s not likely to see this. I get it, he was young and wanted to win this long standing bet and get to know his teenage crush, that part isn’t that bad, but it’s a story that doesn’t age well. A lot of things Kutcher has done don’t age well. He’s matured and grown though, we all have, and I have to say that he looks hot now. What is wrong with me? He needs to get rid of that Shaggy from Scooby Doo beard though.

Comedian Greg Davies was on too. I know him from a show now on Netflix called Cuckoo with Andy Samberg. (That’s mildly funny but it made me cringe too much. I didn’t stick with it. Incidentally Davies is huge, he’s 6’8″.) He told a story about shagging his girlfriend in his parents’ garden and his granddad coming around the corner. That’s well worth watching.

Here’s the video

Also I think Ashton and Mila are cute together. I said it!

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Night out with the wife

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42 Responses to “Ashton Kutcher asked Jennifer Aniston’s then-husband Pitt if he could ask her out (update)”

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  1. Erinn says:

    I know he’s not been the most mature guy throughout the years, but I do like Kutcher. I really enjoyed him on Dax’s podcast a while back as well. He seems to have grown a lot, and I think he genuinely knows that he needed to change.

    • Ericia says:

      So , on a serious note I love Jenn. Always have she’s a hella actor and more so the way she carries herself. So I think, Anywho, that being said Brad was my all time crush, not in a werido way just like Damn, can I tell ya. Up until he made the biggest idoit move and switch sides like a special agent ‘who_d”enny act dumb dumb ‘ You know damn well ‘ you sir are crazy as hell. Other then your beautiful children… N not hate- in the baby’s Momma but damn how you turn Transformer and leave a Dimond in the Ruff.. “so to speak” ..? You ever hear about those ‘ Once in a lifetime people,,. / Your ride n die without doubt. To me that’s how Jenn comes off re-presenting her whole personal character.. As for Mr & Mrs Ashton,,. Again not hate- in just wondering Is it just me or both their facial structural apperences look way different.? Reminded me of ol,, Justin B apperences when he was everywhere you looked concering his Marriage.. I didn’t even recognize who he was … ” Like a sinker in the water without a bobber” Seventies Coke making the rounds…. Just an opinion, more as thought really. No dis respect intented…

  2. Maya says:

    Wasn’t a fan of his until it came out how many women & children he saved from sex trafficking.

    Those people are dangerous and Ashton should be praised for not caring about his & his family’s safety.

  3. lana86 says:

    Why so many women start laying eyeliner on the inner lid, just makes them look older and angrier lol. Her, dushess Kate, Sara jessika Parker, …

    • Erinn says:

      A lot of women do it – It’s to give a smoldering look. I don’t think it makes anyone actually look angry- you’re the first person I’ve heard say that. Meghan Markle has gone through a phase of tight lining as well.

      I actually tight lined mine this morning. Hopefully I look older than my 28 years, as well as angrier and nobody will bother me.

      • DiegoInSF says:

        Mila’s makeup looks flawless in that picture. I don’t get it, “angrier”?

      • Valiantly Varnished says:

        I tightline and line my waterline all the time when I’m going for a smoky look. I also add eyeshadow of course but you cant do a smoky eye and not line your waterline.

    • Josephine says:

      It’s a black-tie event based on his tux, so the heavier make-up is par for the course.

    • Valiantly Varnished says:

      Angry?? It’s called a smoky eye and hers is on point. It’s gorgeous and sultry. When I do a smoky eye I tightline and line my waterline.

    • brutalethyl says:

      I think Mila is beautiful without all the spackle. She (and all women IMO) look so much better with minimal make-up. Highlight the good, distract from the bad, and that should be enough. I don’t like Mila’s look here. I get old Russian peasant woman from it. And don’t jump on me. There’s nothing wrong with old Russian peasant women but it’s not a look Mila needs to cultivate.

  4. Janey says:

    I enjoyed the first series / season of the Ranch but honestly the only reason I continued was because I could close my eyes and listen to Sam Elliott.
    Additionally Greg Davies is one of the funniest men ever. I adore him, especially in The Inbetweeners. Hilariously dry sense of humour.

  5. Torontoe says:

    Now I am morbidly curious as to what you said to get him to block you both? Is it just tagging him in gossip stories?

  6. Babadook says:

    Which article made Kutcher block the celebitchy ladies? I’m very curious!

  7. anp says:

    Question has he not made that statement before.

  8. Zee says:

    If an acquaintance planned to ask my husband out on a date, even as a joke, I would want them to ask me before,too. It has nothing to do with owning another person, it’s just to avoid misunderstandings and problems that can be easily avoided. And if I wanted to do that with a friend’s husband I’d ask her, too. There’s really no need to turn this into a faux feminist issue.

  9. OzJennifer says:

    This is actually a very old clip, from the 2011 series.

    • Celebitchy says:

      Thanks Jennifer I saw the video was new on the Graham Norton YouTube channel and they didn’t write that it was old. Appreciate that and issued an update.

  10. whatWHAT? says:

    I found The Ranch to be painfully unfunny. Plus, it employed a d*ckhead $ci-bot who was then accused of multiple sexual assaults/harassment. they dropped him but the show still sucks.

    as for Kutcher, he’s not my favorite but I’ll forever remember him as the man who made Justin Timberlake cry.

  11. itspurplespice says:

    I hate to be the one to say it, but I LOVE Kutcher and Kunis together. I know he did a lot of questionable shiz but I do feel like marriage and fatherhood have matured him well. They’re really cute together and seem like a happy, grounded couple and I like to see that.

    To answer your questions, hubby and I have watched every season (they don’t call them seasons though, I think it’s “parts”) of the The Ranch. It’s…..ok. It has funny moments and cringey moments. Kutcher’s character is his standard stupid pretty-boy character but it does have a realness to it, especially when paired with his on-screen wife Elisha Cuthbert (who is really good as Abby). Also, although I totally understand why it had to happen (and agree it SHOULD have happened), I will say losing Danny Masterson was a blow for the show. They tried replacing him with a long lost nephew (Dax Shepherd) but it just doesn’t work as well.

  12. K says:

    Mila has aged quite a bit in the last few years and looks much older than her age. she looks much older than her husband now.

    • Kate says:

      Booooo – go home.

    • Snowflake says:

      She does. Unfortunately I feel I am aging faster than a coworker who is 9 months younger than me. I have pronounced crow’s feet and my upper eyelids are starting to sag, sob!

  13. Dee says:

    I’m still curious; did he ever denounce Masterson? I know he’s off The Ranch, but what of their relationship? After all of Kutcher’s work with human trafficking, and even having Masterson work with him and child victims? Are they still friends?

    • brutalethyl says:

      I thought the law was hot and heavy on his trail and then… Nothing. Dead silence. I guess the CO$ threw some (more) money at LAPD and made all the accusations go away. You know, their usual MO when someone comes after one of their money-making stars.

  14. Catherine says:


  15. elimaeby says:

    Okay, I really want to like Ashton. But I get beyond irritated with his “farm boy from the sticks” shtick. My extended family is from his home town (Cedar Rapids, Iowa). His brother dated my cousin. The town has a population of over 250,000 people. He’s always talking about “living on a farm” or “shooting squirrels”. I’m sorry, Kutch, but you are not a country boy. Never were. Normal Midwest small-city kid, sure. The closest this guy has been to being a farm boy is being on that Ranch show on Netflix. It’s just irritating. Enough people think Iowa is just a bunch of bramblef**k yokels. It’s a surprisingly diverse and liberal state when you get into the bigger towns and cities (his hometown included). Rant over. Sorry.

  16. SM says:

    This video is from a while back. Graham Norton has a beard now and had it for about few years now by my count. I am not sure why this video is being recycled.

  17. Shelley says:

    The Ranch is a great show. My husband was a farmer/rancher and this is his favorite show.

  18. Sara says:

    I still can’t believe that Jackie and Kelso got together in real life!