If you’re going to do it, then do it right. Sexting can be great fun, and it’s probably one of the main reasons we’re glad to live in a world with unlimited free texting. But it definitely has the potential to go so wrong, so fast. Anybody that ever accidentally sexted a family member or a friend can attest to that – or worse, one with a picture attached.
Double-check the recipient before you click send. Make sure the person you’re talking to isn’t going to rat you out in public – and definitely confirm the age of the person you’re talking to before you start.
Fortunately, it’s not just everyday people who screw this up. Celebrities suck at it too. Here are some high-profile incidents of failed sexting to make you feel better about your own failures. Don’t let it scare you off if you’ve never gone wrong yet. Take these examples as cases of what not to do, and learn from their pain – or in some cases, just wince. You’ll notice that a lot of them involve infidelity, so… if you’re thinking that sexting would be an easy way to get a little something outside of your relationship?
You’re wrong. You’ll be caught, and you’re a jerk. Don’t do it.
10. Calum Hood
Young Calum Hood has a lot to learn. You may not have even heard of him, but this guy is the bassist from Five Seconds of Summer. In a move that clearly demonstrated he’s still not used to how rabid boy-band groupies can be, Calum sent a Snapchat video of his penis to a fan he’d been exchanging messages with – and now, that video is all over the internet. He took it in his stride, taking to Twitter to boldly state: “Least ya know what it looks like now.” They sure do, Calum. Needless to say, like a true gent, he didn’t spread the fan’s nudes in return.
9. David Boreanaz
Buffy fans, take note. (Yes, we know you exist.) In 2010, while his Playboy model wife Jaime Bergman was pregnant with their child, David Boreanaz clearly couldn’t keep it in his pants. His texts to the woman he was having an affair with – who, coincidentally, was Rachel Uchitel, who’s also connected to Tiger Woods – were later leaked to the media. They weren’t particularly flowery, as anybody who read them can attest, but they caused a real problem for Boreanaz. For some reason, Bergman forgave him, and the pair are now married. Let’s hope he’s learned his lesson. Just send them to your wife instead, David!
8. Tony Parker
This bright spark from the NBA managed to ruin his marriage to beautiful Desperate Housewives actress Eva Longoria by cheating on her, leaving countless texts on his phone for her to find as evidence. You might call it stupid, but clearly the stupidest part of all of this was cheating on somebody as amazing as Eva Longoria. Not only did he cheat on his pretty wife, but Parker actually had numerous flings on the side. That’s surely a reason to hate him forever!
7. Casper Smart
You may know him best as Jennifer Lopez’s ex-boyfriend – he’s a dancer. As it turns out, he’s also a keen sexter – though he may want to rethink that for the future, as clearly he’s not capable of being a very subtle one. Not long after his breakup with Jennifer, he was revealed to have been talking dirty with two Instagram models who happened to be transgender. He’s denied it all, but the evidence speaks for itself – and for the record, Casper, nobody cares if you’ve been talking to transgender models. Those women are gorgeous, and you were single. What’s all the fuss about?
6. Jesse James
Why you’d need to sext another woman when you’re married to Sandra Bullock is anybody’s guess – but that’s exactly what Jesse James did, and it certainly contributed to their divorce. Unfortunately for poor Sandra, she only discovered this infidelity when the woman he was contacting, model Michelle McGee, revealed all the intricate details to the media in one exclusive interview. Clearly he shouldn’t have done it in the first place, but evidently, McGee didn’t hesitate to tell her story. In the future, he might be more careful about who he gets in touch with.
5. Ryan Phillipe
Here’s another married man who couldn’t keep his phone in his pocket and his hands out of his pants – and poor Reese Witherspoon paid the price. She found dirty texts sent to actress Abbie Cornish on her husband’s phone, and it inevitably led to their divorce. No getting mad at your girlfriend if she checks your phone and finds out you’ve been cheating. If there was nothing for her to find, then it’s an invasion of privacy – but chances are if she’s checking, she’s already suspicious. If there is something for her to find, then that’s all on you. Shame on you, Ryan!
4. Ashton Kutcher
Okay, one more badly behaved husband. When Ashton Kutcher ended his affair with his mistress Brittney Jones, she wasn’t having any of it. Though he’d asked her to delete any text messages that would serve as evidence for his affair, fearing that then-wife Demi Moore would find out, Brittney had declined to delete them – and as soon as he ended things, she spread them to the media and beyond. Bad move, Ashton. As soon as you’ve sent the message, you can’t control it anymore; that’s lesson number one when you’re sending dirty texts.
3. Kanye West
Of course Kanye West has a sexting scandal. We’d be more worried if he hadn’t.
When Kanye sent unsolicited pictures of his penis to a handful of female adult entertainers, he probably thought he was doing them a favor; he just didn’t realize what kind of favor it was. After his slut-shaming attacks on Amber Rose, those stars decided it would be a good time to give Kanye a taste of his own medicine, and those sexts came back to haunt him. One picture was sold to the media, and now it’s out there for all to see online. Presumably it hasn’t affected Kanye’s ego much, but no matter what the man himself might think, it still counts as a fail.
2. James Franco
In a move that landed him in hot water, James Franco was revealed to have continued exchanging message of a sexual nature with a 17-year-old girl – after she revealed her age. Granted, this happened in the state of New York, where this is perfectly legal, but clearly, there’s something a little sleazy about a 36-year-old A-list celebrity asking a 17-year-old girl if he should rent them a room. Some people claim this is meant to be a big publicity stunt to promote his movie Palo Alto. If that’s true, it’s almost just as bad. Get a little class, Franco.
1. Anthony Weiner
This is probably the most well-known story on the list, but sorry, it just hasn’t been said enough. The guy’s name is Anthony Weiner, and he got caught sending a d–k pic. You don’t have to be 10 years old to appreciate that. And in case that doesn’t tickle your funny bone, let’s remind ourselves that Weiner was actually texting under an alias. That alias was Carlos Danger.
This guy has actually been hit by sexting scandals twice – once in 2011, and once in 2013. Both times, he was caught sending pictures of himself to women outside of his marriage. It’s not all hilarious, though; one woman who claimed to have had sexual online contact with Weiner was only 17 at the time. If that’s the case, he’s clearly earned his spot as a grade-A sleazebag, as well as the top spot in this list.