18 Celebrity Exes Whose Messy Breakups Will Give You Secondhand Shame

Breakups are never fun. Even if you have every intention to split with your significant other amicably, there are always going to be some tensions between the two of you. It's a sad inevitability. Not everyone can be Miranda Kerr and Orlando Bloom, after all. Of course, there are always going to be people who have zero intention of keeping the peace between them and their ex, and that's when the breakup goes being unfortunate to insanely dramatic. Which celebrities had the most immature, dramatic breakups ever? Click through to find out which celebs you'd never want to date — or at least, never want to dump.

by Kaitlin Reilly

Rita Ora

The “Black Widow” singer’s ex-boyfriend pulled the plug on her singing the song he penned at the Teen Choice Awards.

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Calvin Harris

The DJ and producer wrote his then-girlfriend’s track “I Will Never Let You Down,” but, after their split, he refused to let her sing the tune at the awards show. Ora has stayed mostly mum about the split, stating that it was really just “distance” that drove them apart — but Harris’ behavior read as totally bitter.

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Rob Kardashian

The youngest Kardashian was publicly accused of cheating by his Cheetah Girl ex.

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Adrienne Bailon

Bailon did a tell-all interview with Latina Magazine that called her ex out for cheating on her during their relationship. Kardashian (and his big sisters Kourtney and Kim) fired back at the former Disney star on Twitter, saying that it wasn’t right to kick their brother when he was down for press.

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Ariana Grande

The “Love Me Harder” singer was accused of cheating on her ex with a member of The Wanted.

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Jai Brooks

After learning that Grande was dating Nathan Sykes, Brooks took to Twitter to rant about being cheated on. Dude was not even subtle about it — he called out both Grande and Sykes by name in his rant.

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Katy Perry

The “Dark Horse” singer was devastated when her husband asked for a divorce…

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Russell Brand

…probably because it was over text message. (Yikes.) Luckily for no one, the drama was captured by Perry’s documentary crew.

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Taylor Swift

The “Blank Space” singer may have a lot of exes who would say that she’s insane, and I firmly believe that it’s mostly their problem. The feud between her and this ex might be on both of them, though.

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Joe Jonas

Swift was very candid about the fact that Jonas dumped her via a phone call, and that her song “Forever & Always” was about the middle JoBro. To get back at the singer, Jonas penned a track called “Much Better” about doing, well, “much better” now that his ex is out of his life.

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Lucy Hale

The Pretty Little Liars star’s ex didn’t take their breakup very well, but he did take to Twitter.

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Chris Zylka

The Leftovers actor dissed his ex on Twitter shortly after their breakup, saying that he “didn’t have a girlfriend anymore” because she “thought she was too good.” He since apologized, so props for that… but maybe stay off social media while your heart is still mending.

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Abigail Breslin

The Little Miss Sunshine actress borrowed a page from Taylor Swift’s book of breakups when she penned this song about her ex.

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Michael Clifford

Breslin’s new song “You Suck” is allegedly about this 5 Seconds of Summer guy, though the actress/singer recently denied that they dated at all. If it’s not about Clifford (despite the very specific references to his hair, tattoos, and band), it’s about someone — and it’s so not flattering.

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Rob Kardashian (Again)

Kardashian slammed his pop star ex in a series of tweets, calling her out for cheating on him with “more than 20 guys” and even claiming that he got her pregnant during their relationship.

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Rita Ora (Again)

Not to be outdone, the singer fired back at Kardashian with her own nasty tweets, saying that his “d*** was whack” and that she had to “get it” from somewhere. The tweets have since been deleted. Stay classy, you two.

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Sophia Bush

There is no love lost between Bush and her ex-husband. Like, none. At all.

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Chad Michael Murray

Bush admitted on Watch What Happens Live that she has nothing nice to say about her husband of five months, who allegedly cheated on her during their short-lived marriage in 2005. Apparently the feeling is mutual — Bush also claimed that while she’s “fine” with her ex, he still “hates” her after all these years.

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Paris Hilton

Technically, this isn’t a romantic breakup, but it gets its own place on the list because Hilton’s friendship with this reality star is basically a crash course in what not to do after you breakup with a friend.

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Kim Kardashian

No one is sure exactly what went down between former BFFs Hilton and Kardashian, but my personal opinion is that Hilton just couldn’t handle Kardashian dethroning her as the person most famous for being famous. Both Hilton and Kardashian have thrown shade at one another since their friendship breakup, perhaps most famously with the former Simple Life star saying that Kardashian’s butt looks like “cottage cheese.”

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Naya Rivera

Rivera and her rapper fiancé were supposed to get married, but called off the wedding — and started a bitter war of words.

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Big Sean

Want to know who Big Sean was probably thinking about when he rapped the harsh breakup song “I Don’t F*** With You?” You’re looking at her. The rapper claims he dodged a bullet by not marrying the Glee actress, but Rivera still walked down the aisle just four months after their breakup — just with another guy.

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Lindsay Lohan

The troubled starlet took to Twitter (sensing a pattern here?) to tell the world that her ex-girlfriend cheated on her.

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Samantha Ronson

Not to be outdone, the DJ fired back at The Canyons actress by calling her a “very angry” human being.

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Sandra Bullock

The Blind Side star’s husband managed to both cheat on her and insult her performance in bed. Ugh.

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Jesse James

Motorcycle designer James, who cheated on Bullocks lots during their marriage, told Howard Stern that his then-girlfriend Kat Von Dee was way better in bed than his ex-wife. Way to kick someone when they’re down, James.

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Kim Kardashian

Okay, so the entire world gave Kim Kardashian hell for staying with her then-husband a mere 72 days after her wedding, but no one gave her quite as much flack as the groom himself.

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Kris Humphries

Basketball player Humphries has been vocal about how his marriage to the reality star was a “sham” and that he felt used for fame. Which, to be fair, is exactly how I would feel, too. But there’s a line, dude — one funny Mindy Project cameo and it’s time to move on.

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Justin Bieber

The relationship between the Biebs and his ex-girlfriend was almost more dramatic after they broke up.

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Selena Gomez

I have a feeling that Taylor Swift’s song “We Are Never Getting Back Together” was referencing Gomez and Bieber’s on again/off again relationship with the line “this is exhausting.” Whether these two are Instagramming photos of each other for attention, using the Jenner sisters as pawns to make the other jealous, or penning songs about their breakup, someone should seriously tell them to just move on.

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Brandi Glanville

The Real Housewives of Beverly Hills star seems to be constantly locked into a battle with her cheating ex.

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Eddie Cibrian

Cibrian cheated on Glanville with his Northern Lights co-star LeAnn Rimes, which totally sucks. What sucks even more is the fact that neither party seems very interested in moving on — both constantly rag on one another in the press.

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Amber Rose

Though it’s been almost two years since she dated this rapper, Rose insists on talking about her ex’s cheating ways.

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Kanye West

West is a happily married father, but his ex says that he might not have been the most faithful of boyfriends. According to Rose, West cheated on her with his now-wife Kim Kardashian, and she has gone so far as to call Kardashian a “homewrecker.”

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Mel B.

Most people forget that Mel B. has a daughter with this famous comedian.

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Eddie Murphy

According to the former Spice Girl’s recent tweets, the Dr. Doolittle star doesn’t “bother” with his own daughter. Just in case it wasn’t clear that Mel is pissed, she also tweeted that she penned a new track called “Beverly Hills C**k” about the celeb.

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