The Cringiest Public Figure Sexts of All Time

The Cringiest Public Figure Sexts of All Time

Tiger Woods, Jeff Bezos, and, yes, King Charles, are among some of the worst offenders.

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Photo: Getty

This week, the girlies of TikTok conspired to expose Maroon 5 singer Adam Levine as a serial text cheater—and a weird one, at that. On top of roasting the married father of two (with a third child on the way!) for asking his alleged mistress for permission to name his next child after her, Twitter has since become a cesspool of tweets and memes mocking Levine’s sexts. The sexts in question, are, indeed, dripping with surprising levels of thirst and desperation from a man once named People’s Sexiest Man Alive: “I may need to see the booty,” reads one, with a follow-up that simply says, “Fuckkkkkkkkkkkkkkk.” Another message: “It is truly unreal how fucking hot you are. Like it blows my mind.”

All of this has raised much more important questions: Why are rich famous men so bad at sexting? Is there really such thing as a “good” sext at all?? Maybe all sexts just look a little awkward when decontextualized from the heat of the moment?

But some celebrity sexts are just...unequivocally weird. Might I bring your attention to the leaked (also extramarital) sexts of former Democratic nominee for U.S. Senate, Cal Cunningham, in which he calls a woman “historically sexy 😘” and says her proposition to hang out “sounds so hot and so fun!”

And because this world is apparently a bottomless pit of horny, entitled, famous men, there’s more, much more where that came from. Join me in perusing a bunch of rich, famous people’s cringe written attempts at flirting and fucking—and thank god they have money, because I have a feeling they’d be living pretty lonely lives without it.

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Jeff Bezos

Jeff Bezos

All the money in the world apparently cannot buy a single ounce of game. Case in point: I give you Amazon founder Jeff Bezos’ leaked sexts to his partner Lauren Sanchez from 2019, while he was still married to ex-wife MacKenzie Scott, in which Bezos sent a string of X-rated nude photos, as well as texts reading: “I love you, alive girl. I will show you with my body, and my lips and my eyes, very soon.”

Another text: “I want to smell you, I want to breathe you in. I want to hold you tight.… I want to kiss your lips…. I love you. I am in love with you.” It gets better, still, and by better, I mean worse: “You know what I want? I want to get a little drunk with you tonight. Not falling down. Just a little drunk. I want to talk to you and plan with you. Listen and laugh.” Live love laugh!!!

Let’s not forget the particularly passionate caps lock texts: “I basically WANT TO BE WITH YOU!!! Then I want to fall asleep with you and wake up tomorrow and read the paper with you and have coffee with you.”

If you’ve ever felt embarrassed before, I implore you to read the above screen-shotted texts in their entirety. You will feel much better!!

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Tiger Woods

Tiger Woods

God, these were so good, although tragically-slash-predictably enough, Woods was also married. And there are so many more texts like these, permanently archived in the New York Post, though they’re more befitting of the MoMA. I’ve taken the liberty of pasting some highlights below:

  • Tiger: quiet and secretively we will always be together
  • Tiger: send me something very naughty
  • Jaimee: some things are worth waiting for lol … besides im at work
  • Tiger: go to the bathroom and take it

At some point in October 2008:

  • Jaimee: well I appreciate you not wanting to wake me up but if y couldn’t sleep I would have rather sat up and talked to u more … find out why I keep falling more and more for u ;)
  • Tiger: Because I’m blasian :)

On Thanksgiving:

  • Tiger: happy thanksgiving to you
  • Jaimee: u too love
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Cal Cunningham

Cal Cunningham

Well, from reading these, it probably wouldn’t surprise you to learn Democrats lost that Senate seat! Cunningham, you’ll recall, is married, and so was the woman with whom he was cheating on his wife. Yet, for two people who were horny enough to cheat on their spouses, their “sexts”—if you can even call them that—were pretty tame. By the looks of it, these two just wanted to kiss, like, a lot!

“Sounds so hot and so fun!” Cunningham replies to a text soliciting him. His mistress then tells him to “starch your white shirt, and be ready to kiss a lot.”

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King Charles

King Charles

King Charles and Camilla Parker-Bowles’ once-extramarital relationship obviously predates sexts and racy Instagram DMs. But phone calls were apparently still a thing, and audio of those calls got leaked in 1989. You can read a transcript of the call above, in which it seems quite clear Charles had a tampon kink. Anyway, that’s the new King of England, everyone!

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Ben Affleck

Ben Affleck

Bennifer is going strong, but there was once a 20-year stretch of time during which the couple was broken up. And during those two decades, Affleck was sure getting his cringe on. In May 2021, when a TikToker unmatched him on Raya, he sent her a two-second video message asking in a vaguely sultry tone, “Nivine, why did you unmatch me? It’s me.”

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Adam Levine

Adam Levine

Back, briefly, to the man who started it all: Adam Levine. There’s truly no living any of this down. But arguably the most embarrassing part? As one Twitter user wrote, “the best part of the adam levine sexts is that u know he was getting all worked up meanwhile this girl was probably eating fettuccine alfredo on the couch and laughing with her friends about it.” We’ve all been there!

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Andrew Broad

Andrew Broad

Andrew Broad, a married, former member of Parliament and assistant minister to the deputy prime minister of Australia, resigned from his post in 2018 after a string of quirky texts to his mistress were leaked and caused quite the scandal in the island-continent. One of his sexts to the mistress, whom he reportedly met via a sugar baby network, reads: “I pull you close, run my strong hands down your back, softly kiss your neck and whisper G’day mate.” He continued: “I’m a country guy, so I know how to fly a plane, ride a horse, fuck my woman. My intentions are completely dishonourable.”

Say what you will, but at the very least, he was repping Australia: “G’day mate,” indeed!

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G-Eazy

G-Eazy

Image for article titled The Cringiest Public Figure Sexts of All Time
Photo: Getty

In 2018, while dating singer Halsey, noted white rapper (derogatory) G-Eazy was exposed for exchanging racy Snapchat messages with a woman in London, and his sexts were about as uninspired as his music. After she sent a nude photo, he replied, “Damn... you got some ass on you shorty.”

“Ha thanks. How’s your 🍆,” the woman sent back.

He responded by predictably begging for another nude: “Lemma see the front tho 👀”

The rapper appears to have eventually responded with a precise number when the woman asked, yet again, how big his dick was. But the Daily Star, for whatever reason, deprived us of this by censoring it. That’s just bad journalism!

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Armie Hammer

Armie Hammer

Armie Hammer is currently under investigation by the Los Angeles Police Department for allegedly “violently” raping a woman for four hours in 2017. That is, certainly, the most important revelation from his inappropriately, widely-memed cannibalism scandal of 2021.

For the purpose of this slideshow about rich people’s total and complete inability to sext, I’d just like to enter into the record that Hammer’s consensual sexts are pretty fucking embarrassing. One of the above messages, in which he tells a woman, “You are like the Michael Phelps of fucking,” isn’t necessarily awful in itself—it’s the sad little follow-up apology that makes it weird: “Wow. Ok, sorry that came spilling out and I feel badly.”

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