The Messiest Celebrity Love Triangles of All Time

When you think of famous Hollywood love triangles, Jennifer Aniston, Brad Pitt, and Angelina Jolie might be the first trio to come to mind. After months of whispers from the set of Mr. & Mrs. Smith, the buzz around co-stars Pitt and Jolie was hard to ignore. But then, Aniston and her husband suddenly went on a holiday vacation in the Caribbean, and all felt right with the world. But as the story goes, Pitt finally confessed his true feelings for Jolie on that trip — and they announced their split on Jan. 7, 2005.

“We would like to announce that after seven years together we have decided to formally separate. For those who follow these sorts of things, we would like to explain that our separation is not the result of any of the speculation reported by the tabloid media,” they told People in a joint statement. The tabloids were never the same as Brangelina was officially born and Aniston had to weather over a decade of headlines that locked her into that love triangle whether she liked it or not.

Author Kate Andersen Brower believes that another Hollywood drama predicted the path for Pitt’s love conundrum. It was Elizabeth Taylor’s entanglement with Eddie Fisher, who just happened to be married to America’s sweetheart, Debbie Reynolds. You see the pattern: the bad girl, the All-American girl, and the handsome guy caught in the middle. Just like Reynolds, Aniston “got all of the sympathy,” but Brower thinks that the situation was always more “complex” than how the media portrayed these love triangles. “Elizabeth didn’t set out to obviously destroy anyone’s life,” Brower shared with SheKnows.

It’s easy for fans to get sucked into the gossip and firmly plant themselves in one corner or the other — #TeamAniston or #TeamJolie. But as time unfolded, people finally saw that Pitt might have been the bad guy in the situation, not the women. In Taylor and Reynolds’ era, the studios took “advantage of the situation to make money.” Brower added, “They pitted these two women against each other so that they could sell tickets to movies and help create this love triangle image.” In Jolie and Aniston’s era, it was a cash grab for the tabloids back when we all bought entertainment magazines.

In the end, though, does anyone win in a love triangle? It’s rare for an affair couple to stay together, although there are a few exceptions to the rule. Check out some of the juiciest entanglements over the years and find out who is still together.

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Eddie Cibrian, Brandi Glanville, & LeAnn Rimes

An Us Weekly cover blew the lid off of Eddie Cibrian’s affair with LeAnn Rimes while they were filming the 2009 movie, Northern Lights. The problem was that Cibrian was married to Brandi Glanville, and Rimes was married to backup dancer, Dean Sheremet. Glanville went on to Real Housewives of Beverly Hills fame where she spilled the tea about Cibrian and Rimes.

Bridget Moynahan, Tom Brady, & Gisele Bündchen

Tom Brady’s relationship with Bridget Moynahan got awkward very quickly when they broke up in 2006 after two years together. He quickly rebounded with supermodel Gisele Bündchen only to learn that his ex-girlfriend was pregnant with their son, Jack. “Going through that traumatic time of being heartbroken and then being pregnant turned my whole life upside down and inside out and just knocked the wind out of me,” Moynahan explained to Harper’s Bazaar in 2008. “But I got so much out of that.”

Brady married Bündchen in 2009 and they share two children, Benjamin and Vivian. They divorced in 2022.

Jennifer Garner, Ben Affleck, & Christine Ouzounian

Jennifer Garner weathered a stormy marriage to Ben Affleck while he was working on his sobriety, but things got really choppy when he allegedly had an affair with their children’s nanny, Christine Ouzounian. However, Garner denied that tale in a Vanity Fair interview, noting, “We had been separated for months before I ever heard about the nanny. She had nothing to do with our decision to divorce. She was not a part of the equation.”

Jay-Z, Beyoncé, & ‘Becky With the Good Hair’

Fans still don’t know the confirmed identity of “Becky With the Good Hair,” but Beyoncé gave us as many clues as she could in her 2016 masterpiece, Lemonade. The affair between Jay-Z and “Becky” is also what reportedly set Solange Knowles on fire as she attacked her brother-in-law in an elevator after the 2014 Met Gala. A drama for the ages!

Jennifer Aniston, Brad Pitt, & Angelina Jolie

Brad Pitt and Jennifer Aniston were the golden couple of Hollywood after they married in a lavish $1 million ceremony in Malibu in 2000. Their romance was abruptly halted in 2005 after Pitt worked with Angelina Jolie on Mr. & Mrs. Smith — and the gossip storm was set ablaze! By 2005, Pitt and Aniston had announced their divorce and Pitt and Jolie made a splashy debut in paparazzi snapshots with three-year-old Maddox. (Us Weekly reportedly paid $500,000 for the images.)

Brangelina expanded their family to six with Pax, Sahara, Shiloh, and twins Vivienne and Knox joining their big brother. The couple married in 2014 and divorced in 2019.

Prince Charles, Princess Diana, & Camilla Parker-Bowles

The royal drama that started it all: Prince Charles, Camilla Parker-Bowles, and Princess Diana. Back in the day, the royal protocol required brides to be virgins when they married, so Charles knew he couldn’t marry Camilla despite his true love for her. She married Andrew Parker-Bowles in 1973 and Charles found his pure bride in Diana, whom he married in 1981.

However, it wasn’t long before Camilla came creeping back into the picture which caused years of tabloid headlines. Diana famously called them out in her 1995 Panorama interview, “Well, there were three of us in this marriage, so it was a bit crowded.” The royal couple divorced in 1996, Charles married Camilla in 2005, and she is now Queen Camilla since he became king.

Will Smith, Jada Pinkett Smith, & August Alsina

If you’re wondering where the word “entanglement” came from, look no further than Jada Pinkett Smith’s affair with August Alsina while married to Will Smith. The story first surfaced in June 2020 when Alsina admitted he had a fling with Pinkett Smith in 2015 while he was friends with Pinkett Smith’s son, Jaden — yep, a 21-year age gap.
 
While Alsina claimed the couple had an “open relationship” that was not something Will nor Jada had shared publicly. So, a very awkward Red Table Talk episode happened with Will and Jada admitting they had hit a “rough patch” in their marriage. “I was in a lot of pain, and I was very broken,” she said during the episode. “I just wanted to feel good. It had been so long since I had felt good.
 
Fans would later learn they had privately separated for seven years and have since reunited.

Dennis Quaid, Meg Ryan, & Russell Crowe

What happens when America’s Sweetheart hooks up with one of Hollywood’s bad boys? Lots of chaos. That exact scenario went down in 2000 when Meg Ryan and Russell Crowe started an affair on the set of Proof of Life. The problem is that Ryan was married to Dennis Quaid at the time.

Ryan took a lot of the heat for the affair even though she alleged that Quaid wasn’t exactly faithful to her during the marriage. Crowe and Russell lasted less than a year and their movie bombed at the box office.

Jesse James, Sandra Bullock, and Michelle “Bombshell” McGee

Less than two weeks after Sandra Bullock earned an Oscar for her performance in The Blind Side, the actress was blindsided by the news that her husband, Jesse James, had multiple affairs. Michelle “Bombshell” McGee, a San Diego tattoo model and stripper, was one of the most public faces during the scandal.

McGee had sold her story to a tabloid, and James admitted the affair just hours before the story was published. “I admitted the affair. I told her the hard details. I let her know that I had never loved this woman, that I had never cared for her at all,” he wrote in his 2011 memoir, American Outlaw. “The feeling of shame and sadness that washed over me as Sandy began to cry was almost beyond measure…I didn’t touch her. I sat frozen in my chair, watching, as Sandy’s small body shook with sobs.”

The couple divorced in 2010.

Debbie Reynolds, Eddie Fisher, & Elizabeth Taylor

This love triangle between Eddie Fisher, Debbie Reynolds, and Elizabeth Taylor has all of the glitz, glamour, and drama you would expect from Old Hollywood. Fisher and Reynolds were there to comfort Taylor when her third husband, Mike Todd, died in a plane crash. But Fisher got a little too close for comfort with Taylor and their raging affair stole all of the headlines.

Fisher and Taylor married in 1959 and ended up divorcing in 1964 because someone else entered the picture: Richard Burton.

Lilly Jay, Ethan Slater, & Ariana Grande

Ariana Grande found herself in a love square while she was married to Dalton Gomez. It seems that she fell in love with her Wicked co-star, Ethan Slater, while he was married to his high-school sweetheart, Lilly Jay. While Grande continues to deny that there was any overlap between the two relationships, sources on the set claimed that she and Slater were “sloppy” about hiding their romance — and Jay publicly blasted her husband’s affair partner.

Jay told Page Six in the middle of the scandal, “[Ariana’s] the story really. Not a girl’s girl. My family is just collateral damage.” Grande is divorced from Gomez while Jay and Slater are still working out the details of their split.

Jason Sudeikis, Olivia Wilde, & Harry Styles

The set of Don’t Worry Darling was fraught with controversies, and Olivia Wilde’s alleged affair with Harry Styles while she was engaged to Jason Sudeikis didn’t help. The timelines between the former couple didn’t line up, but Wilde doubled down on denying that she overlapped her Sudeikis and Styles’ romances.

“It’s obviously really tempting to correct a false narrative … But I think what you realize is that when you’re really happy, it doesn’t matter what strangers think about you,” she told Vogue in 2021. “All that matters to you is what’s real, and what you love, and who you love.”
 
Styles and Wilde dated for two years before they split in November 2022, and the Booksmart director is amicably co-parenting her two children, Otis, and Daisy, with Sudeikis.

Billy Crudup, Mary-Louise Parker, & Claire Danes

Mary-Louise Parker and Billy Crudup were expecting their first child together in 2003 when he abruptly left Parker to be with Claire Danes after meeting on the set of Stage Beauty. Danes seemed rather casual about the affair, telling Howard Stern, via Us Weekly, in 2015, “I was just in love with him,” she shared. “And needed to explore that, and I was 24… I didn’t quite know what those consequences would be… But it’s O.K… I went through it.”
 
Danes stayed with Crudup until 2006.

Gwen Stefani, Gavin Rossdale, & Mindy Mann

Gwen Stefani and Gavin Rossdale seemed to have the ideal Hollywood marriage until allegations about his affair with their nanny, Mindy Mann, surfaced. The pop star reportedly discovered explicit texts and nude photos between the nanny and her husband of 13 years on the family iPad — talk about awkward!

Stefani shared that the discovery of Rossdale and Mann’s betrayal “was the beginning of hell.” She told Harper’s Bazaar, “Like six, seven, eight months of torture—trying to figure out this big secret.” She divorced her husband in 2015, and soon found love and trust in Blake Shelton whom she’s been married to since 2021.

Taylor Swift, Joe Jonas, & Camilla Belle

Taylor Swift and Joe Jonas were enjoying a young, sweet romance when he suddenly broke up with her in a 25-second phone call. It turns out there was a reason for his shocking behavior, he already had Camilla Belle on speed dial.
 
Swift wasted no time writing a song about Jonas, “Forever & Always,” and she didn’t exclude Belle either. The actress is written about in Swift’s song, “Better Than Revenge.” Belle and Jonas broke up in 2009 after a year of dating — young love is fickle.

Billy Bob Thornton, Laura Dern, & Angelina Jolie

Laura Dern found herself in a jaw-dropping situation when her boyfriend of three years, Billy Bob Thornton, took off and married Angelina Jolie while Dern was out of town. “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,” Dern told Talk magazine, via ABC News, in 2000.

Jolie and Thornton divorced in 2003, but not before wearing vials of each other’s blood around their necks. The early aughts were strange times!

Shania Twain, Mutt Lange & Marie-Anne Thiébaud

Nobody could have ever predicted this outcome for Shania Twain after her husband of 15 years, Mutt Lange, suddenly asked her for a divorce. The pop star confided in her best friend and assistant, Marie-Anne Thiébaud, for advice. “I said, ‘Marie-Anne, don’t you think my husband is acting strange?'” Twain told Oprah Winfrey. “And she said, ‘No, I don’t see anything strange.'”

Well, there was something strange going on because her bestie was sleeping with her husband. Twain then sought comfort from Marie-Anne’s husband, Frédéric Thiébaud, who was also going through some heavy emotions from the betrayal. The duo eventually fell in love and got married on New Year’s Day in 2011. “We slowly became very, very good friends. We had many months of just trying to make sense of everything,” Twain told Ellen DeGeneres. “Holding each other up was a very difficult time emotionally for both of us. And we really found something very beautiful in the end and unexpected.”

Ryan Phillippe, Reese Witherspoon, & Abbie Cornish

Reese Witherspoon and Ryan Phillippe married young and had their first child, Ava, in 1999, but seven years later trouble loomed ahead. There were rumors that Phillippe was hooking up with his Stop-Loss co-star, Abbie Cornish.

Phillippe denied the cheating allegations and told People in 2008, “It was unfair for [Abbie] to be called the names that she was because it wasn’t about that. I don’t think an outside person can ever cause a divorce. I had difficulties in my relationship, and in my marriage, long before I ever met her.”

Phillippe and Cornish dated for four years after his divorce from Witherspoon.

Arnold Schwarzenegger, Maria Shriver, & Mildred Baena

There were always whispers about Arnold Schwarzenegger stepping outside of his marriage to Maria Shriver, but it took 25 years for him to be caught— and no one expected his affair partner to be the family’s housekeeper, Mildred Baena. Not only did the cheating occur in the couple’s bedroom, but the action star had also fathered a son with Baena, Joseph, who eventually appeared on the 31st season of Dancing With the Stars.

Aaron Carter, Hilary Duff, & Lindsay Lohan

Hilary Duff and Aaron Carter were the cutest teen couple back in 2001… until Carter thought it was a great idea to date Lindsay Lohan at the same time. It was a messy drama for years and one that was spoofed during Lohan’s 2004 Saturday Night Live monologue, even though the love triangle ended in 2003.
 
Carter had the nerve to try and date Duff again years after they split by professing his love to her on Twitter in 2014. The Lizzie McGuire star turned him down.

Kevin Federline, Britney Spears, & Shar Jackson

Kevin Federline was a backup dancer to Britney Spears when he caused a whole mess of chaos for girlfriend Shar Jackson, who was six months pregnant at the time with their second child. “One day, when I had bad morning sickness and was about six months pregnant, Kevin had an audition for a Coke commercial or something in LA … then I didn’t hear from him for three days,” Jackson told the Daily Mail.
 
Just days after her son, Kaleb, was born, Federline and Spears got engaged and the paparazzi went wild. It was a tumultuous time in the pop star’s life, and the love triangle certainly didn’t help the narrative. Spears and Federline were married from 2004 until 2007 and had two sons together, Sean Preston, and Jayden James.

Rachel Leviss, Tom Sandoval, & Ariana Madix

You had to be hiding in a cave to miss the “Scandoval” of 2023 when Vanderpump Rules stars Rachel/Raquel Leviss and Tom Sandoval had an affair behind Ariana Madix’s back. Sandoval and Madix had been in a decade-long relationship and owned a house together, and Leviss was one of Madix’s closest friends. Let’s just say, it was messy.
 
Sandoval became the world’s most hated man, and he has never taken ownership of the affair to this day. Leviss entered a mental health facility and now hosts a podcast, Rachel Goes Rogue. Madix is living her best life after coming in third on Dancing With the Stars, earning a starring role in Chicago on Broadway, and helming the upcoming season of Love Island.

Woody Allen, Soon-Yi Previn, & Mia Farrow

This love triangle is extremely uncomfortable to this day. Woody Allen was in a relationship with Mia Farrow for 10 years. The actress already had six children (three adopted and three biological) from her marriage to André Previn, including daughter Soon-Yi Previn. Allen took on a stepfather role to Farrow’s kids, and the couple went on to have son Ronan Farrow, and adopt three more children.

In 1992, all hell broke loose when the news of Soon-Yi’s year-long affair with Allen became public. Let’s remember, Allen was 56 and she was 21 years old at the time. The couple married in 1997 and they adopted two daughters together.

Allen has also been subject to sexual abuse allegations from daughter Dylan Farrow. He has never been charged with a crime, but he lost his Amazon production deal as a result of the accusations.

Vivian Liberto, Johnny Cash, & June Carter

Anyone who has watched Joaquin Phoenix and Reese Witherspoon in Walk the Line knows this love-triangle tale very well. Johnny Cash was happily married to Vivian Liberto after years of a long-distance relationship during his military years. Once he hit the road to make it big in country music, touring life and his alcohol and drug addiction took hold — and that’s when June Carter entered his life.

Their affair led to Liberto filing for divorce and paving the way for Cash and Carter to get married. They were together until she died in 2003.

Stephen Colletti, Kristin Cavallari, & Lauren Conrad

Stephen Colletti’s love triangle with Lauren Conrad and Kristin Cavallari on MTV’s Laguna Beach was teen love at its finest. He flip-flopped between the two women even though Conrad was the one everyone was rooting for. Now that 20 years have passed, Conrad believes the viewers got the story wrong.
 
“I think one of my takeaways from looking back is I’m like, ‘It’s really sweet.’ You guys were in love, and you had a relationship,” she told Colletti and Cavallari on their Dear Media podcast Back to the Beach with Kristin and Stephen. Nobody wound up together in the end, but Cavallari admitted that she and Colletti shared a little make-out sesh during an August 2020 reunion.