John Mayer, 45, spotted on a date with 22-year-old Kiernan Shipka


This is somehow surprising and yet not surprising at the same time. John Mayer, 45, was spotted on a date over the weekend with Kieran Shipka, 22. They went to Giorgio Baldi on Sunday night and enjoyed a four hour dinner and serenade. According to eyewitnesses — I mean, onlookers — they arrived separately, dined together, and left separately, but apparently at some point they pulled over and Kieran got in John’s car, but was dropped off at her own home. Ew, all of this, ew.

John Mayer and Kiernan Shipka were seen meeting up to get a bite at Giorgio Baldi on Sunday, November 6. The musician, 45, and actress, 22, were both spotted arriving separately at the Santa Monica eatery in new photos, which you can see here, via DailyMail. The pair reportedly spent four hours at the restaurant and onlookers told the outlet that John even began singing to Kiernan later in the evening.

As John arrived, he rocked a warm, black jacket over an olive-green t-shirt, along with gray pants and white sneakers for the evening. Kiernan rocked a long, black charcoal trenchcoat, over black pants and a pair of burgundy heels. The Chilling Adventures of Sabrina star looked gorgeous with her blonde hair parted down the middle, as they arrived at the restaurant.

The Santa Monica date wasn’t the first time that John and Kiernan were seen out together. The “Your Body is a Wonderland” singer was seen meeting with the actress at the Sunset Strip’s Tower Bar to get drinks back in February. The pair were seen embracing as they arrived for the evening out together.

The dinner date came about two weeks after John’s ex-girlfriend Taylor Swift, 32, dropped her latest album Midnights on October 21. Shortly after the record dropped, the “Anti-Hero” singer’s fans quickly started speculating that the track “Would’ve Could’ve Should’ve” referred to her romance with John, which she also sang about in her Speak Now song “Dear John.” Fans drew a parallel between a line from the 2010 song, and the lyric where Taylor sings, “I damn sure never would have danced with the devil at 19,” in the Midnights tune. Fans thought that lines like “Give me back my girlhood, it was mine first,” were written about the Sob Rock star.

[From Hollywood Life]

So is this still on? They were spotted together before, including in February. Or is it on again? Either way, it’s gross. Despite technically being an adult woman in her 20s, Kieran seems (and looks) so young, like too young to be dating a 45-year-old man. And I often judge celebrity dating age differences on whether or not I would have done it at that age and 45 would have been a bridge too far when I was 22, even if he was extremely cute, which John Mayer is not. Also, he’s John Mayer! Notoriously sleazy and pretentious and misogynistic (not to mention kind of racist, with his “David Duke D”). The way he’s talked about his previous relationships has been quite disrespectful and even he’s really embodying that Taylor Swift lyric about getting older while the girls stay the same age. Even if it wasn’t about him, it’s still a bad look. I’ll excuse Kiernan because everyone dates inappropriate people in their early 20s and she’s not the first young woman to fall for his supposed charms. But don’t publicly date John Mayer. Giorgio Baldi means they wanted to be seen. And the singing is so ew and cringe too. Did John sing his own song — one he wrote for/about someone else? The whole thing is just ugh.

photos credit: Avalon.red and Cover Images

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

60 Responses to “John Mayer, 45, spotted on a date with 22-year-old Kiernan Shipka”

Comments are Closed

We close comments on older posts to fight comment spam.

  1. Hannah says:

    Nooo. Please please please don’t let this be *a thing* I adore Kiernan. I mean I watched every episode of Sabrina 🫣 I watched Mad Men for the 1st time recently. With hindsight you can see she is low key in teen lust with John Hamm/Don Draper in Mad Men. But John Mayer 🤮

    • XOXO says:

      People on this site were just praising Cher and her 40yr age gap with her new beau.
      Are we upset because it’s John Mayer, or that it’s a May-Dec relationship?

      • Beth says:

        I say this as someone who also thinks the age gap between Cher and her boyfriend is gross.

        There is a big difference in dating and life experience between a 22 year old and a 36 year old (Cher’s boyfriend’s age). Your brain (executive function) is also not finished developing at age 22. These are not equivalent scenarios.

      • AMA1977 says:

        There is a world of difference between Cher’s mid-70’s “dating” a mid-30’s man, and John Mayer’s 45 (JOHN MAYER!!! Notorious for being a f^ckboy) dating an early 20’s starlet. Yes, she’s an adult, yes it’s legal, and it’s STILL creepy. She does not have the wisdom and maturity of someone even 5 years older. If she were my daughter I’d be waiting for the fallout. John Mayer has dated every cute blonde up-and-comer for the last 20 years and he’s just gross. Also, I think the Cher thing is weird, but less alarming and more :::shrug:::

        Also, an aside, I recently listened to “Room For Squares” again with MY 45 year-old ears for the first time since it was on constant repeat when it came out, and MAN. He has not grown or matured ONE BIT since he put that album out. It was charming and sexy (IMO) when we were both 25, but now?? He’s still in arrested development, and those of us in his former fanbase have marriages, careers, kids, and mortgages. Continuing to date women 20+ years his junior is not a good look, but he doesn’t have the emotional depth for anyone older to bother with him.

      • XOXO says:

        First- I said what I said.
        Second- John Mayer is gross.
        Third- Cher is gross.
        Fourth- Despite brain development not being completed until age 25, KS may believe herself to be more mature than the average 22yr old, because of all she has been exposed to, and earning her keep since she was a child.
        Fifth- I said what I said.

      • BayTampaBay says:

        Kiernan Shipka dating some one 45 years old does not bother me in the least.

        Kiernan Shipka dating John Mayer DOES bother me BIG TIME.

      • C says:

        I agree with AMA1977.

      • Normades says:

        Probably an unpopular opinion here but when both parties are over 30 and want the same things out of the relationship I am ok with age differences (example the Clooneys).
        Afterwards it’s a cliché but I think the half + 7 rule is actually pretty correct. That said Cher’s relesh doesn’t make it but he’s a grown ass man.

      • Normades says:

        Also would I say the same if the tables were turned? Yes I would. A 36 year old woman dating an almost 80 year old dude: Gross but yer a grown ass woman. However a 22 year old dude dating a 45 year old woman à la Kate Beckinsale? Nope. I side eye her like Leo.

    • mel says:

      So, JM tried to have sex with me when I was 19. This was 14 years ago, but I kid you not…. I am going to edit the next sentence as cautiously as possible. We were at the tour wrap party for whatever tour he was on, and I knew one of the guys in his road band so I was invited.

      He came up to me and said:
      “I am going to take you back to my hotel room, lay you on the couch, and make you sq**rt.”

      I laughed in his face. He got really angry. His guys kept telling me I had to go with “the boss.” I didn’t. He pouted. Overall, he’s so gross.

      • OriginalLaLa says:

        holy crap, that is sickening. I’m so sorry you experienced that – he is gross.

      • Persephone says:

        @mel I think I love you!
        I too would have laughed in his face.
        He is looking at creepy in the rear view mirror.

      • AMA1977 says:

        OMG, grooooosssss. I’m so glad 19 year-old you laughed in his face and wasn’t intimidated by his idiot pimps in the band. That’s disgusting and they should all be mortified. Like, he may be THEIR boss, but you’re YOUR boss. F^ckwits, all of them.

      • Emily says:

        Gross. He thought he could just order you off the menu and to his bedroom?

        Dear Kiernan, if you don’t believe Taylor Swift at least read what Jessica Simpson who was an adult when they dated has to say about him.

      • Tiffany:) says:

        That is so disgusting that he said that to you! I am so happy you laughed in his face. Well done.

  2. Barrett says:

    It does make you think that Mayer has an inappropriate fetish for girls not woman. I’m puking in my mouth. Pervert in plain site.

    • Snoozer says:

      He’s not just gross and sleezy. From Jessica’s memoir and Taylor’s songs, (along with Katy’s references to needing more therapy when he’s brought up) there are clear patterns of manipulative behaviour, emotional abuse, and highly toxic behaviour.

      I highly encourage people to either read Jessica’s memoir or listen to the You’re Wrong About podcast episodes that cover it. You will never look at this guy the same way again. The shit he put her through… my god! Mind-blowing fuckery.

    • Mel says:

      Yeah I was a teenager when he came after me…. and I looked like an absolute baby. There was no mistaking my age.

  3. Shanaynay says:

    I’m totally with you on this. Everyone knows his reputation, so I would be weary about dating a guy like him. I wouldn’t advise her to expect anything too much out of this relationship. Maybe he’s really good in bed which is why he gets all these beautiful women??

    • Lee says:

      My first thought always is that he must be good in bed. Or he at least has an extra 20 years of experience on her peers. Or it’s quite possible that because he’s getting his older, his drive is more manageable than guys her age. I can’t imagine there aren’t other men even ten years older that wouldn’t fit the bill. I’ve never found him attractive (like, I don’t think he’s physically unattractive, but if he were a random guy on bumble I’d probably swipe left), there must be something about him that is appealing though. Ugh.

    • Emily_C says:

      He’s manipulative. That’s all that’s necessary. And women with some experience can see it. Very young women are much easier to lovebomb and puppeteer.

  4. Mle428 says:

    The header shot of John Mayer made me lol. Also I 100% judge romances by “would I have at 22…” and I might have? I had a thing for older musicians and a terrible picker at 22.

    That being said I turned down any trophy girlfriend opportunities with much older men, so who knows? I worked in the film industry in LA so there were definitely opportunities.

  5. PaperclipNumber99 says:

    Oh, Sweetie. No. Just…no. You are too good for this. Oh well. As Kaiser says, we all date the wrong guys sometimes.

  6. hangonamin says:

    really?? why?? way to not listen to anything ever said bout him. In your early twenties, you inevitably date some d*bags and losers, but don’t be exploited by this gross grown man…ugh. i don’t care how amazing of a musician, or even how great in bed he is…

  7. Geegee says:

    Ewwww

  8. Jessamine says:

    Just here to add my voice to the chorus of ewwwwwww nooooooo.

  9. ElsaBug says:

    I feel like I have known that John Mayer is gross for longer than Kiernan has been alive?

  10. Miss Owlsyn says:

    Honestly, if I were a famous actress or singer and I had the opportunity to go on a few dates or have a fling with someone I had an enormous crush on when I was younger? I totally would. A lot of people would.

  11. CTgirl says:

    Gross.

  12. Lucy says:

    Don and Betty, come get your daughter!

  13. María says:

    This is beyond creepy and predatory behavior! Kiernan get the F out!

  14. Miss Owlsyn says:

    This might not be a popular comment but, Kiernan is 22, not 16. I personally would not date John Mayer but at what age are women allowed to make their own decisions without needing to be ‘protected’ from their choices?

    • Bettyrose says:

      ITA. She’s a grown ass adult and he’s a known racist whose creepy with women. If she is in fact dating him that’s 💯% on her. I’m just leaving a tiny window of hope open that she’s not.

    • C says:

      Well that would be why people are side-eyeing it and not physically restraining her.

  15. teecee says:

    At least it’s not still BJ Novak? Although…maybe Novak is better than Mayer?…Sorry tough to figure out where all these gross Hollywood guys lie on the scale of grossness.

    She looks very Hollywood now. My guess is she’s not getting the quality or level of offers she did during Mad Men and is trying to play up the “starlet dates older men” route to drum up interest. There are a lot of cute kid actors who grow up less cute and then they’re lost.

    I hope she goes to college soon.

    • Normades says:

      She was the lead in her own series and does a lot of Netflix stuff so she’s doing OK. But it’s gotta be hard being a young actress that everyone said was so promising to make that transition to young adult roles. She’s probably in competition with Millie Bobbie Brown for every role and neither have the career of Florence Pugh.

      But just to add to the chorus: Girllll……nooooooooo!

      • JaneBee says:

        After watching Kiernan in Sabrina, it became clear that her acting range is fine, but not great (and that is accounting for the hit or miss writing quality). It was disappointing after seeing her as Sally in Mad Men.

        For at least a year, Kiernan was very publicly dating and apparently head over heels in love with a grandson or great nephew of Francis Ford Coppola? There were some very sappy Instagram pics.

        JM is just disgusting.

      • Normades says:

        Agreed she was the less interesting character in that show. And somehow Camilla Mendes and Lilli Reinhard make it work.

  16. Bettyrose says:

    He’s not kind of racist. Racist is his whole identity. I judge any one who dates him after he outed himself. Kieran Shipka is a grown ass adult who knows his history or racist comments and gross behavior with women. But it makes no sense that she’d be dating him in a world of men who are him. It could be some kinda work/contractual thing?

  17. lucy2 says:

    You know, no matter how many women shout from the rooftops that a guy is awful, there’s always one who thinks “I can fix him”. Please, let it not be Kiernan, because she is so very young, and he is so very gross.

  18. Goldie says:

    Haven’t there been rumors about these 2 for a long time? I wouldn’t be surprised if they’ve been quietly hooking up for years, and they decided to go public now that Kiernan is over 21.

  19. Queen Meghan’s Hand says:

    I thought he was dealing with Larry David’s daughter?
    When I was in my twenties, I absolutely did not want to sex middle-aged men. They would approach me but why would I want an old man to slip and slide all over me? Ew. I don’t get it.

    • Saba says:

      Yes! They have been seen together for years! She’s popped up on insta at his house in Montana. But it was made to sound like they were friends and seeing other people. If they are dating, it may be far longer than we think.

      Yes, it is gross! Young people will always make bad choices. It’s the responsibility of the older person to stop that from happening. Yet there’s always someone who’s willing to milk a young person’s naivety/vulnerability/stupidity for their own needs 🙁

      My rule is if you’re going to have a large age hap, both parties need to be over 30, this way it’s a considered choice and both parties know what they’re getting out of the transaction.

  20. Winnie Cooper’s Mom says:

    I would just like to point out that “Your Body is a Wonderland” was released when she was a toddler.

  21. MaryContrary says:

    I know DeuxMoi is not totally reliable, but according to reports on that (supposedly via his friends) they are not dating, he wouldn’t date her, and they are just friends. It’s implied that she has a big crush on him. I know he’s had a bad reputation, so anything is possible-but I guess time will tell.

    • ally says:

      I read DM as well and just agree…this wouldn’t work They call him safe sex, he isn’t going to date a child.

    • Candy says:

      So, according to him, she wants him but he doesn’t want her. This sounds like something an old, entitled douche would say. And he’s spending time with her so yes, he’s interested.

  22. Christine says:

    I thought she was in a long-term relationship with Christian Coppola?

    • JaneBee says:

      @Christine This was my understanding as well, but the lovey dovey posts with Coppola on Insta seem to have stopped in past 12 months?

  23. Stef says:

    Leave Sally Draper alone, you gross, dysfunctional, lecherous pervert!

    I’m actually a John Mayer fan and have been for about 20 years, his music and live shows are great! Just can’t stand him as a person, especially after reading what he put Jessica Simpson through – he’s toxic AF!

  24. Emily says:

    There was an interview where John talked about Taylor drawing between takes of a video, and how she looked like a child when she did. Then he pursued her.

    I love the line in her song Would’ve, Could’ve, Should’ve where she calls him a “promising grown man.”

  25. Mabs A'Mabbin says:

    OMG the way he’s always talked about his conquests. Run Kiernan. RUN!

  26. Emily_C says:

    It’s not 100% on her, any more than it would be for any abuse victim at any age. Emotional abuse and manipulation are abuse. It’s not her fault, any more than being punched would be.

    Here’s the deal: I don’t like Taylor Swift. I only like one of her songs. HOWEVER, when I read her lyrics about John Mayer, I’m like “Oh, yep, been there.” (Except when for some reason she wants her girlhood back — why the hell do you want to be a teenager again?) Anyway, I think of men like Mayer as Iagos. They get you dancing however they want until you don’t know who you are any more.

    Source: My life. My first boyfriend was my age, so there are young men like this too, Lack of age gap does not mean safety. He eventually told me he liked me best because I was the most challenging person to manipulate that he’d ever met, and that he liked treating me like a rat in a maze. I was so turned inside out by then, I stayed with him. Until, one day, for no reason I’ve figured out, I didn’t.

  27. jferber says:

    These pigs are just SOOO predictable!!!!

  28. jferber says:

    I bet he thinks he looks soulful in the header pic, but he just looks like a constipated poseur.

  29. Lorelei says:

    I’m not side eyeing the age gap necessarily, she’s 22 not 18 and grew up in Hollywood, plus as someone in my 20’s I would have totally gone for some of my favourite band’s singers who were all in their 40’s. I think your 20’s are when you need experiences (good and bad) to truly discover who you are and what you really want in a partner.
    But…John Mayer????? Yeeeewwwwww . That I do side eye and hard.

  30. Serena says:

    Ewwww Kiernan, noo.