10 Juiciest Celebrity Love Triangles of All-Time

For some, the symbol of love is more triangular than heart-shaped. And for celebrities, those shady relationship happenings are aired out like dirty laundry in the media and tabloids.

While some Hollywood couples can withstand the test of time, others find themselves embroiled in a three-way relationship they weren’t expecting.

From teen relationship drama between Hilary Duff and Lindsay Lohan over pre-teen heartthrob (and self-confessed player) Aaron Carter to the seriously confusing interworkings of the KarJenner family’s shared beaus, these celebrity love triangles made for some of the juiciest drama of all time.

Can you recall them all? Keep scrolling to read the dirt on these feud-inducing scandals.

Hilary Duff, Aaron Carter, Lindsay Lohan:

In perhaps the most legendary teen love triangle of all-time, singer Aaron Carter met child star Hilary Duff on the set of her Disney Channel show Lizzie McGuire. The pair dated for two years, but during that time, he also began dating child actress Lindsay Lohan.

“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,” Carter later revealed of the drama. He went back to Duff later, but she denied him on Twitter, crushing 2000s pre-teen hearts yet again.

Still, the actresses held longterm grudges after the drama and Lohan even took to the Saturday Night Live stage in 2004 to mock Duff. As for Carter, he has since revealed himself as bisexual.

Jennifer Aniston, Brad Pitt, Angelina Jolie:

The speedy transition from Brennifer to Brangelina remains one of the biggest celebrity relationship scandals, despite happening more than 12 years ago.

Jennifer Aniston and Brad Pitt were Hollywood’s “It” couple when they began dating in 1998; they married after two years together in a $1 million celebration in Malibu and held strong until 2005, when they announced their plans to divorce. During that time, Pitt had begun working with Angelina Jolie on Mr. and Mrs. Smith, then they became a public item soon after the divorce announcement.

As time went on, Pitt and Jolie became a beloved celebrity couple and the pair, who have welcomed six children together, married in 2014. In September 2016, Jolie reportedly filed for divorce citing irreconcilable differences, though reports claim Pitt was accused of hitting one of their children on a flight.

Billy Corgan, Courtney Love, Kurt Cobain:

Courtney Love and Kurt Cobain will always be considered one of rock ‘n’ roll’s most iconic couples, but their relationship began when she was still linked to another famous rocker.

Love originally dated Billy Corgan of The Smashing Pumpkins in the early ’90s, but she later revealed in an interview that the two broke up because Corgan wouldn’t pay for her to fly home after a show. His band was playing shows with Nirvana at the time, so she ended up staying with the Nirvana band members after her fight with Corgan.

She then began a relationship with Cobain and the pair were married from 1992-1994. The couple welcomed a daughter together, Frances Bean Cobain, in August 1992. Love later claimed Frances Bean was conceived on a night she was meant to see Corgan.

Kylie Jenner, Tyga, Blac Chyna, Rob Kardashian (and Travis Scott):

For the Kardashian clan, a love triangle would be too simple, so they created a love pentagon of sorts to keep it in the family.

Rapper Tyga and Blac Chyna originally dated in 2011 after she starred in his music video for “Rack City.” They welcomed son King Cairo together and became engaged before they called it quits in 2014. After the pair split, they apparently set their sights on members of the KarJenner family.

Tyga began dating Kylie Jenner in the same year as his breakup with Chyna, and Chyna began dating Jenner’s older brother Rob Kardashian in 2016. After a few months of dating, Kardashian and Chyna announced their engagement and revealed they were expecting a daughter together, Dream Kardashian, who was born in November 2016. The couple split soon after, but Chyna has since been embroiled in a legal battle with the entire KarJenner family, whom she says killed her opportunities on reality TV.

Meanwhile, Tyga and Jenner called it quits in April 2016, then she quickly moved on to rapper Travis Scott, with whom she welcomed daughter Stormi Webster in February. Sources claim Tyga is reportedly calling for a paternity test, believing the newborn could be his child.

Kris Humphries, Kim Kardashian, Kanye West:

Kanye West set his sights on Kim Kardashian long before the pair got together in spring 2012, but she was preoccupied with her relationship and eventual marriage to NBA player Kris Humphries.

Kardashian and Humphries were legally married from 2011 until their divorce was finalized on June 3, 2013, but she and West had already begun a longterm relationship, welcoming daughter North West only 12 days after her divorce was final.

In West’s 2012 track “Theraflu,” he rapped, “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.” The bars seemingly confirmed that West was interested in his now-wife while she was still involved with Humphries, who then played for the Brooklyn Nets, which Jay-Z partly owned.

Since then, West and Kardashian married in 2014 have welcomed 2-year-old son Saint and daughter Chicago, born in January via surrogate.

Laura Dern, Billy Bob Thornton, Angelina Jolie:

Actor Billy Bob Thornton lived with his fiance, actress Laura Dern, from 1997 to 1999 and the pair shared a dog together. While Dern was away filming a project, Thornton swifty broke off the relationship and went on to marry Anjeline Jolie only months later.

“I left our home to work on a movie,” Dern told Talk magazine, “and while I was away, my boyfriend got married, and I’ve never heard from him again. It’s like a sudden death. For no one has there been any closure or clarity.”

Thornton and Jolie, who infamously wore vials of each other’s blood around their necks as a sign of their commitment, divorced in 2003 after three years of marriage.

Faith Evans, Biggie Smalls, Lil’ Kim:

Singer Faith Evans was married to Notorious B.I.G. when she walked in on rapper Lil’ Kim in their bed, she revealed in her memoir Keep the Faith: A Memoir. After she caught the pair, Biggie admitted to having a lengthy affair with Kim and reportedly cheated on Evans with several other women.

Despite the drama, Evans and Biggie remained married from 1994 until his death in 1997, though the pair separated shortly before his killing.

Years later, the women in B.I.G.’s life have made amends, Evans told Shade 45 radio. “My issues with Kim really went out the window when B.I.G. passed, to be quite honest,” she said. “It’s something that people always kind of talk about, but it’s certainly nonexistent. Thankfully now, she’s in a different place where she can kind of receive how I was already feeling. It’s all good.”

Brandi Glanville, Eddie Cibrian, LeAnn Rimes:

LeAnn Rimes was married to Dean Sheremet and Eddie Cibrian to Brandi Glanville when the pair met on the set of their Lifetime movie Northern Lights in 2009. Soon after, the co-stars left their respective spouses to start a relationship of their own, causing a fierce, ongoing feud between Rimes and Glanville.

Glanville, who went on to become a cast member of The Real Housewives of Beverly Hills, detailed in her published tell-all the night of karaoke when she realized Cibrian and Rimes were having an affair.

“When… LeAnn awkwardly pulled my husband (not hers!) onstage for an awful karaoke rendition of Sonny and Cher’s ‘I Got You Babe,’ I just about lost it,” she wrote. “Was she serious? I felt like I was in the twilight zone.”

Cibrian and Rimes married in 2011, though Glanville swears they “will divorce” eventually.

Robert Pattinson, Kristen Stewart, Rupert Sanders:

Actress Kristen Stewart found love on the set of two of her most famous films. The Twilight actress began a relationship with co-star Robert Pattinson in 2008, but the pair broke up after photos of her kissing Rupert Sanders were published by Us Weekly in 2012. Sanders, who was directing Stewart in Snow White and the Huntsman, was married to model Liberty Ross at the time.

After apologies were issued, both couples seemed to be trying to work things out, but in 2013, Pattinson moved out of Stewart’s home and Sanders’ wife filed for divorce.

Pattinson moved on by becoming engaged to FKA Twigs, but the pairs called off the relationship in October. Meanwhile, Stewart revealed herself as a bisexual and has been dating Victoria’s Secret model Stella Maxwell since 2016.

Britney Spears, Kevin Federline, Shar Jackson:

Kevin Federline was dating his pregnant fiancée, Moesha star Shar Jackson, with whom he already shared a daughter, in 2004 when he left the relationship for pop princess Britney Spears.

After only five months of dating, Federline and Spears were married and she soon became pregnant with their first child together, son Sean Preston. The couple were married from 2004-2006, during which time they welcomed another son, Jaden.

Because Federline got in a relationship with the “Toxic” singer while Jackson was pregnant with his child, the high-profile romance received major negative attention, with many slamming him as a “gold digger.”

Jackson later commented that Federline’s relationship with Spears “wasn’t like just breaking up a relationship; it was like breaking up a family.” After the split, Jackson created a cosmetics line called RelationLips with the first lip gloss named “He Cheated.”