Breaking up sucks for anyone, but it sucks doubly for celebrities. Not only do celebrities have to feel bad about the breakup but the media discusses it in detail. The sorted details of the breakup end up in People Magazine and while some of those details may be true, others may be complete fabrications.
Thankfully though, for those unfortunate celebs going through a breakup, it seems that celebrity couples are constantly breaking up and making up. For the most part, we’ll read the juicy details about a certain breakup for a week or maybe a month, but then the breakup will be old news. Of course, there are the breaks we read about for years. I think people are still talking about the Jennifer Aniston/Brad Pitt/Angelina Jolie love triangle and it’s been a decade.
While breakups come and go, there are some celebrities who it seems are particularly awful to break up with. The reasons, of course, will vary as to why these celebs are the worst to break up with but, regardless, they are celebrities you would not want to break up with. Some celebs will talk negatively about the person they broke up with to the media. That is awful considering the person they were with trusted them with the private details of their life. Other celebrities like to turn their heartbreak into art and this can be a problem as well. How much would you enjoy seeing a movie or hearing a song about you and your failed relationship? It would be embarrassing and painful.
While we’ll probably never get the chance to actually date any of these celebs, we may be better off because the 15 people on this list don’t always react well to a breakup.
15 Kanye West
Kanye called Rose a 'stripper gold-digger' by tweeting at Wiz Khalifa saying, “you let a stripper trap you." Not only did Kanye insult Rose on Twitter, but he also did so in his song, with lyrics stating: 'My ex said she gave me the best years of her life, I saw a recent picture of her, guess she was right.' Well, way to make your heartbreak into art, I guess? Although, Kanye doesn't seem very heartbroken, rather just angry.
He also said in an interview that he had to take 30 showers after dating Amber Rose before Kim Kardashian would have sex with him. Rose responded by suggesting that Kanye, uh, was interested in some backdoor activity for himself while they dated, which Kanye denied. So, maybe Amber Rose had the last laugh after all, though if I were Kim I'd probably not break up with him any time soon.
14 Taylor Swift
Considering Tay-Tay has basically built her music empire off of being broken up with, you should understand why she’s one of the worst celebs to break up with. Almost every single hit song she has was written about an ex of hers and, for the most part, all of her ex-boyfriends are also pretty famous, which makes her songs just that much juicer.
For whatever reason, guys still flock to Taylor despite the fact that after they break up, Taylor’s next number one hit single will be about their sex life. Okay, we get why guys still flock to her. I mean, she has legs for days. So far ol’ Tay had written about Harry Styles (“I Knew You Were Trouble”), Jake Gyllenhaal ("The Last Time"), and Joe Jonas ("Last Kiss").
13 Alanis Morissette
Alanis Morissette makes this list for one song: "You Oughta Know". This song is up there with "I Will Survive" and "You’re So Vain" as one of the best breakup songs ever written, but the wrath in Morissette's lyrics truly sets it apart.
With lines like “It was a slap in the face how quickly I was replaced. Are you thinking of me when you f**k her?” and “Every time I scratch my nails down someone else’s back, I hope you feel it… well, can you feel it?” it’s easy to see how can easily this became an anthem for anyone with a broken heart.
What makes the song even more interesting is the fact that it may have been written about Uncle Joey from Full House – yes, the creepy uncle with the puppet. Dave Coulier briefly dated Alanis in the early 1990s and claims have been made that he’s the ex in the song. Alanis has kept quiet on who actually inspired the song.
Either way, if she’s capable of writing such harsh but catchy lyrics, it’s best to not break her heart.
So, this one is totally hypothetical because she’s married to Jay Z and despite rumors following the release of Lemonade, they don’t seem to be spilling any time soon.
The thing about Beyonce is, well, she’s Beyonce. Once you date Beyonce, there’s really nowhere to go but down. I mean, where are you going to find someone who looks as beautiful, sings as well, or dances as great as Beyonce? Here's the answer: you're probably not going to find that person anywhere.
Even worse, if you broke Beyonce’s heart, her beehive would probably order your execution. No, but seriously, her fans are insane and they would not be down with anyone breaking up with their queen.
Also, Beyonce’s Lemonade shook up the whole world, as everyone was wondering who the hell Becky with the good hair was, so it’s probably best to not give Beyonce any material for her music.
11 Any Of The Kardashians
Say what you will of the Kardashian and Jenner family but they really believe in the whole ‘blood is thicker than water’ thing. On more than one occasion, the sisters have jumped to the defense of one another via social media, and boy, do they have large social media followings. We’re talking millions and millions of people following each of them so all together they probably have like 500 million followers.
Getting called out on social media after breaking the heart of a Jenner or Kardashian is just about the best possibility for the break up scenario. The worst possible scenario would be that you appeared on KUWTK – just ask ol’ Kris Humphries how he felt about the whole experience.
Furthermore, the family is tabloid bait. Anything they do winds up in magazines and on the internet. If you were to break up with any of them (and there are quite a few of them), you would also likely wind up being under the microscope of the media.
10 Kate Upton
Okay, so there are many girls who could be in this category: Kate Upton, Emily Ratajkowski, Emilia Clarke and basically anyone else considered one of the hottest women in Hollywood. These women are so gorgeous that there is really nowhere to go but down.
Could you imagine breaking up with Emily Ratajkowski then crying yourself to sleep as you replay the "Blurred Lines" videos over and over again? Of course, Seth MacFarlane does have some personal experience to this situation, as he dated The Mother of Dragons for a short period. No, I'm being serious. Somehow Seth MacFarlane convinced Emilia Clarke to date him. I wonder if he can bear to watch Game of Thrones anymore. Considering how hot she is and the amount of nude scenes she's done in the show, I'm going to guess that he probably skips watching this on Sundays.
I know they say beauty is only skin deep and all, but seriously, these women are too hot to ever get over.
9 Gwyneth Paltrow
When you break up with Gwyneth Paltrow, it isn’t like a normal break up because she’s perfect and tends to do everything better than normal people.
When Gwyneth and Chris Martin announced their split, Gwyneth stated that they were consciously uncoupling… whatever that means. If you’d actually like to know what that does mean, her lifestyle website, GOOP, posted a whole article on it. Instead of reading it though, I can sum it up: conscious uncoupling is breaking up. It’s, like, literally the same thing, except Paltrow gave it a new name because she can't just break up with someone. Simply breaking up is so common.
She is also the queen of the backhanded compliment, which is truly an art form in some ways. In response to Chris Martin and Jennifer Lawrence’s relationship, Gwyneth reportedly said, “He could do worse.” Alright, Gwyn, I see you.
8 Jennifer Lawrence
Well, first things first, Jennifer Lawrence is currently America's #1 Sweetheart, but she's a bit more than your average sweetheart. She's always insisting that she's just like all of us normal people. She likes to eat and watch Keeping up with the Kardashians. She even tripped when she was walking up the stairs to accept her Oscar! Don't you just hate when that happens?
Despite her whole not-filtered brand, she is usually pretty good at keeping her private life private. However, after her break up with Chris Martin in 2015, in an interview, she raised her glass to the reporters and said, “Cheers to my hymen growing back!”
That's 100% not the worst thing she could say. She's basically making a joke about her sexless life following her break up with Chris Martin. The issue is that anything she says becomes another click-bait article so her little cool-girl jokes following a break up tend to be very much talked about. It's best not to date someone who is so willing to let the media in on those little details.
7 Russell Brand
When the marriage between Russell Brand and Katy Perry ended, who would have thought that Brand would be so harsh towards his ex? Sure some of the lyrics to some of her songs are corny, but what’s so wrong with her? She’s a gorgeous singer with a rocking bod and she even does Super Bowl halftime shows with people in shark costumes.
Well, after the split Brand stated that he was living a “vapid, vacuous, plastic, constructed, mindless celebrity” life with her. Ouch. Ouch times 1000. That is harsh. This clearly makes Brand one of the worst celebs to break up with. Anyone who would willingly say something so hurtful about you to the press is not good to break up with.
At least Katy Perry is still a gorgeous singer with a rocking bod. She’ll bounce back just fine.
6 Leo DiCaprio
I mean, who really breaks up with Leo DiCaprio? No body. Absolutely no one in the world should break up with Leo. He’s Jack Dawson from Titanic, ‘king of the world’ and now, an Oscar-winning actor. He seems like he’s the smoothest celebrity in the biz so instead of breaking up with Leo, for the most part you should be trying to lock that down.
Unfortunately, breakups are a two-way street so Leo could easily be the one breaking with whomever it is that he is dating. Despite who does the breaking up, Leo would be one of the hardest celebrities ever to get over. You would have to avoid watching any of his movies ever, except for maybe The Revenant. He, uh, doesn't look so hot in that movie. But he's still Leo.
Also, if you were to break up with Leo, he’d be sad for 2.5 seconds and then be on to having sex with his next model-of-the-week on his yacht or whatever.
5 Demi Moore
Shortly after the split, Moore was rushed to the hospital after doing whip-its (inhaling nitrous oxide). She followed that up by checking into rehab for an eating disorder and pill addiction. While one cannot be sure that the breakup drove Moore to this place, she did seem in control until her split with Kutcher.
To make matters worse, Moore had to deal with Kutcher getting together with Mila Kunis very shortly after their split. Breaking up with someone who will have a public meltdown is not the most desirable situation to be in.
4 Jennifer Aniston
After the whole Brad Pitt/Jennifer Aniston/Angelina Jolie triangle, Aniston became America’s favorite sweetheart. People seriously started to adore her and there are a few logical reasons why.
First if all, Jennifer Aniston was pitted against siren Jolie, who literally looks like some kind of Greek goddess living in our modern society. Because Aniston had those girl-next-door looks and lost her man to the sultry Jolie, women began to love her.
Furthermore, Aniston looked hot after the divorce. Like, super hot. She started running and drinking Smartwater (that’s her secret, right?) then appeared on the cover of GQ wearing just a tie.
So, everyone loves her and wants her to have her happy ending – that is what leads to Jennifer Aniston being one of the worst celebs to break up with. Every guy she dated following Pitt had to put up with all the labels flung at him after breaking up with Aniston. Also, anyone she breaks up with ends up in tabloid magazines so that's another issue.
3 Matt Damon
Matt Damon seems like an odd addition to this list. He's been married for ten years to a normal woman, who was just like the rest of us when he met her. She was working as a bartender at a bar when he met her, which seems like some unrealistic romantic comedy but apparently that's for real how Matt Damon met his wife.
The issue with breaking up with Matt Damon is that he's just so damn likable. I cannot imagine anyone not liking Matt Damon and how horrible it would be to break up with someone who is basically loved by everyone in the world. That would be so annoying, right? He's also friends with a lot of people in Hollywood, like Ben Affleck, George Clooney, and Brad Pitt. Would you really want to break up with someone who counts those guys as his besties?
2 Woody Allen
Woody Allen is one of the worst people in Hollywood to break up with for several reasons. First of all, Allen uses some of his personal life experience for inspiration for his films. It is widely known that his film Manhattan pulls pieces from his relationship with Stacey Nelkin.
The larger reason as to why you shouldn't break up with Woody Allen is that be may date your daughter. After being with Mia Farrow for 12 years, the pair split and Woody Allen began dating her adopted daughter, Soon-Yi Previn. Since Allen never married Farrow, he was not legally Soon-Yi's step-father so I guess that makes it less weird, right?
The whole family tree gets even odder when you think about the fact that Mia Farrow and Woody Allen had a biological son together, who would have then been Soon-Yi's brother. See, I told you the family tree gets weirder.
Allen went on to marry Soon-Yi in 1997.
1 Justin Timberlake
If you don’t want a song and music video made about your supposed infidelities, don’t breakup with JT. After Britney Spears allegedly cheated on Justin, he went on to write “Cry Me A River”, but he didn’t stop there.
He then made a seriously hot video about his revenge and even cast an actress who looked like Britney to be in it. I suppose that's the dice you roll when you break the heart of a musician.
Britney went on record “Everytime” in response to JT’s “Cry Me A River”. I guess when two singers have an ugly breakup they can both go the route of singing songs about the other.