Barry White famously told us on The Message is Love that “love ain’t easy.” Anyone that’s spent any length of time in a relationship would probably agree with the legendary crooner. This sentiment seems to especially be true for celebrities, as so much of their relationships unfold in the public eye and are subject to the opinions and criticisms of fans all over the world.

But still, they persist — they enter into relationships, go public with them, and then, more often than not, have them fall apart right as everyone’s watching. Sometimes they fall apart for the most basic reasons — conflicting schedules, etc. — but once in a while, they’ll fall apart for super scandalous reasons. Like a love triangle. We’ve rounded up the 16 juiciest celebrity love triangles for you — proving that everything from teenage drama to co-worker proximity can be to blame for making love not easy at all.

16. Laura Dern, Billy Bob Thornton, And Angelina Jolie

Angelina Jolie is most famously remembered for her role in another love triangle, but, long before Brangelina happened, she had a hand in the ending of a different relationship. Actress Laura Dern had been engaged to Billy Bob Thornton for years before Angelina came around. Then, suddenly, Laura found her engagement called off, and her actor fiancé married to a Hollywood wild child. She told Talk magazine, “I left our home to work on a movie, and while I was away, my boyfriend got married, and I’ve never heard from him again.” Which, if you ask us, sounds like the cruelest way to learn that you’re a part of a love triangle.

15. Jenifer Aniston, Brad Pitt And Angelina Jolie

Of course, no celebrity love triangle list would be complete without us discussing what when down between Jennifer AnistonBrad Pitt and Angelina Jolie. Jennifer Aniston was just wrapping up the final season of Friends when she married Brad in a massive $1million Malibu wedding. The it-couple remained married for five years and were literally the darlings of Hollywood before they announced their divorce and almost simultaneously Brad’s relationship with Angelina went public. Brad and Angelina met on the set of Mr. and Mrs. Smith, and not six months after his divorce news hit the tabloids the new couple announced that they were expecting. Talk about a slap in the face!

14. Taylor Swift, Joe Jonas And Camilla Belle

Taylor Swift has been accused of being too open about her relationship history and current loves. For example, she revealed to Ellen DeGeneres on an episode of her talk show that her famous ex Joe Jonas had dumped her in a 25-second phone call back in 2012. Then a few months later she told Us Weekly that he’d done it because he’d met Camilla Belle. Then a few months later she gave us even more juicy gossip, on her song “Better than Revenge,” when she sang “She’s not a saint/ and she’s not what you think/ She’s an actress/ She’s better known/ for the things that she does/ on the mattress.” This was one celeb love triangle that never had any chance of staying under the radar.

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13. Brandi Glanville, Eddie Cibrian And Leann Rimes

Brandi Glanville has found success both as a model, she spent 17 years modeling for some of the biggest names in the industry, and as a reality star, spending several years as cast member of The Real Housewives of Beverly Hills, but one place she didn’t have too much success in was as the wife of actor Eddie Cibrian. Brandi was married to the soap star for almost nine years before it came out that he was having an affair with country singer-turned-actress, LeAnn Rimes. Eddie and LeAnn met on the set of their Lifetime movie Northern Lights and felt enough of a connection that they both ended up leaving their spouses and moving in together. In one of her tell-all memoirs, Brandi revealed that she learned of the affair when LeAnn pulled her husband up on stage for a rendition of Sonny and Cher’s ”I Got You Babe.” Awk!

12. Dita Von Teese, Marilyn Manson And Evan Rachel Wood

Marilyn Manson and Dita Von Teese are two of the strangest personalities in Hollywood, so it makes sense that they fell in love and ended up getting married in 2005. In fact, it made so much sense that a lot of people were left scratching their heads after Von Teese filed for divorce a little more than a year later. Until that is, Manson stepped out with the then-19-year-old actress Evan Rachel Wood. People immediately began speculating that Marilyn and Evan were having an affair, a fact that’s been all but confirmed by the three in interviews over the years. The new couple stayed together for the next four years, and only split when Evan called off the engagement in 2010, but there’s still no sign of Dita and Marilyn ever reconciling.

11. Naya Rivera, Big Sean And Ariana Grande

Naya Rivera has a bit of a reputation in Hollywood for being dramatic and unreliable, so take this one with a grain of salt. In her 2016 memoir Sorry Not Sorry, the former Glee actress revealed that her engagement to rapper Big Sean was called off because of a love triangle. She alleges that she walked in on someone whose name “rhymes with Smariana Schmande” chilling on her fiancé’s couch and that she wasn’t having it. Not long after the two publicly called it quits, Big Sean made his first public appearance alongside Ariana Grande. But that relationship didn’t last either, as Big Sean is now cuddled up with Jhene Aiko and Ariana with Pete Davidson. It should also be noted that Naya actually married Ryan Dorsey on the exact date she and Big Sean were set to wed. Something sketchy happened, and this just might be a love-square instead of a triangle.

10. Blac Chyna, Tyga, Rob Kardashian And Kylie Jenner

This one is really more of a love square, too, rather than a love triangle, but it’s so bizarre that we had to include it. Blac Chyna and Tyga dated first — getting together in 2011 and welcoming son King in 2014. The two split not long after King was born, and Tyga low-key began dating his new, very young girlfriend, Kylie Jenner (although they didn’t make it “official” until Kylie turned 18 almost a year later). Understandably, Blac Chyna wasn’t too happy with her ex’s decisions, which, most people believe, is what caused her to start hanging out with Kylie’s half-brother Rob Kardashian in 2016. Rob and Chyna had their daughter, Dream, that same year, and the youngest Jenner and Tyga split in 2017, but this celebrity love triangle really gives new meaning to keeping it all in the family. I mean, Kylie’s niece’s half-brother’s dad is her ex-boyfriend. The webs we weave.

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9. Miley Cyrus, Nick Jonas, Selena Gomez

In another teenage nightmare, Disney Channel stars Nick JonasMiley Cyrus and Selena Gomez found themselves in a torrid love triangle. Nick and Miley dated first, and while they weren’t super public about it (there weren’t dozens of couple pics all over their Instagrams), fans definitely knew. But then Nick broke up with Miley and started hanging out with Selena, which had the Miley camp all riled up. Until Nick ended things with Selena and went back to Miley and things settled down. The whole situation had everyone convinced that Selena and Miley were in a massive feud, something that Selena shut down years later, telling W magazine “We never feuded. We both liked the same guy when we were 16.” Nobody said that young love was easy. But that doesn’t explain that time MiCy sang her track “FU” to a Selena cardboard cut-out during one of her concerts.

8. Robert Pattinson, Kristen Stewart And Rupert Sanders

For Twilight fans, Kristen Stewart and Robert Pattinson’s real-life relationship was nothing short of a fairytale. Watching Edward and Bella be blissfully in love felt like a wonderful extension of the fantasy world. Well, until Bella starting sleeping with a werewolf, that is. One of Kristen’s first projects after the Twilight franchise wrapped up was playing Snow White in Snow White and the Huntsman. It was during the filming of that movie that she was caught – on camera – cozying up to her director Rupert Sanders. For a while, it seemed like Robert and Kristen may have been trying to work things out, but eventually Sanders’s wife filed for divorce and Robert moved out, and teenage girls’ hearts everywhere were broken.

7. Faith Evans, Biggie Smalls, Lil’ Kim

Biggie Smalls was one of the biggest names in rap in the ‘90s and remains one of the biggest names in rap today. His life and early death have been the subject of many, many documentaries and biopics. But one piece of juicy information these films don’t always cover is the love triangle that existed between Biggie, Faith Evans and Lil’ Kim. Biggie married Faith in 1997, and the two remained married until he died. But in her memoir, Faith discussed the time she walked in on Biggie in bed with Lil’ Kim, which finally confirmed the rumors that swirled for years about the relationship between the two rappers. The ladies have made amends these days. “My issues with Kim really went out the window when B.I.G. passed, to be quite honest,” Faith said.

6. Reese Witherspoon, Ryan Phillippe And Abbie Cornish

Reese Witherspoon met Ryan Phillippe at her 21st birthday party in March 1997 and married the actor in June 1999. The couple had two children together (who are eerily their exact clones), and all seemed happy and joyous in the Witherspoon-Phillippe home. But then, in 2006, the pair announced in a joint statement that they were separating. Right away, rumors began spreading that it was because Ryan had been getting a little too close to his co-star Abbie Cornish— rumors that he didn’t do much to squash when he began dating her almost immediately. Oof!

5. Orlando Bloom, Miranda Kerr And Justin Bieber

Miranda Kerr and Orlando Bloom were one of the most beautiful couples in Hollywood for the entire six years they were together. The Victoria’s Secret model and her actor beau had a picture-perfect life (including their adorable son Flynn), but that still didn’t stop them from separating in 2013. But it’s what happened after their divorce that’s the juiciest. In 2014, Bloom got into a fistfight with Justin Bieber in a restaurant in Ibiza. The beef? According to gossip at the time, Bloom didn’t appreciate how heavily Bieber was coming on to his then-wife during the 2012 Victoria’s Secret fashion show. In another love square-ish twist, Orlando was soon spotted getting cozy with Selena Gomez in LA – JB’s ex.

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4. Kris Humphries, Kim Kardashian, Kanye West

Kim Kardahsian and professional basketball player Kris Humphries had one of the most legendary and shortest marriages in all of Hollywood. After about six months of dating, the two married in a widely-televised ceremony and began the process for their divorce a mere 72 days later. Today, Kim is, of course, married to Kanye West. The two began dating while she was still legally married, which caused plenty of fans to raise their eyebrows, but things got even crazier when Kanye release “Theraflu.” The rapper spit “And I’ll admit, I had fell in love with Kim / around the time she had fell in love with him / Well that’s cool, baby girl, do your thing / Lucky I ain’t had Jay drop him from the team.” Whoops! West seemed to confirm that he was interested in his wife while she was still with her ex, and started pursuing her while she was still involved in that relationship. Kris also stalled his divorce to Kim while she was pregnant with Kanye’s baby – just adding a little more feul to the fire. Drama!

3. Kate Hudson, Alex Rodriguez And Cameron Diaz

Arguably, Alex Rodriguez’s cutest relationship is the one he shared with Jennifer Lopez. But long before romance sprung up between those two, Rodriquez was in a relationship with actress Kate Hudson. Shortly after A-Rod and Kate’s relationship ended, Cameron Diaz was spotted leaving the baseball player’s New York City apartment with overnight bags in hand. It was quite a scandal as the two women had been really close friends for years, attending all kinds of events together. Allegedly Kate was “pissed” with her gal-pal, which we can’t blame her for, any way you look at it that’s a pretty bad friend move.

2. Britney Spears, Kevin Federline And Shar Jackson

Star Jackson is most famous for her role as Niecy Jackson on the TV show Moesha, on which she starred alongside Brandy for six seasons. Later on in life, she was also famous for being in a relationship with backup dancer Kevin Federline. In fact, the two were even engaged, and share a daughter, Kori, and a son, Kaleb. But in 2004, Kevin left Shar while pregnant to start shacking up with Britney Spears. Shar took the high road and didn’t bash Kevin too much in the media, but she did start a cosmetics line, RelationLips, and the name of her first lip gloss (“He Cheated”) sent a pretty strong message.

1. Hilary Duff, Aaron Carter And Lindsay Lohan

OMG. As a teenager, the drama between these three was pretty all-consuming and definitely made you doubt love. Aaron Carter and Hilary Duff dated for about 18-months, and were every early ‘00s teen’s #relationshipgoals. Then Lindsay Lohan came along and everything went to pot. Aaron opened up to a tabloid about the mess, saying, “I started dating Hilary on my 13th birthday. I was dating her for like a year-and-a-half and then I just got a little bored so I went and I started getting to know Lindsay, dating Lindsay.” Not long after that interview, he dumped Lindsay and went back to Hilary (what’s with all these teenage dudes getting back with their exes?), and things were never right in the world again.

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