Top 10 Most Complicated Celebrity Love Triangles

Love triangles are complicated enough with people who aren’t related, so imagine how messy things can get when a mother and daughter are involved. In August 2023, Tish Cyrus, the mother and manager of musicians Miley and Noah Cyrus, got married to actor Dominic Purcell. While Miley served as her mother’s maid of honor, Noah oddly skipped the wedding to spend the day at Walmart. The situation became clearer when reports surfaced that Noah and Purcell had been romantically involved before he started dating Tish. An insider claimed that Tish pursued Purcell when he was still seeing Noah, then blocked her on Instagram and barred her from attending the wedding. Oh, to be a fly on the wall at the Cyrus family thanksgiving dinner.

Justin Bieber’s high-profile romantic life has been widely covered over the years. He began dating Selena Gomez in December 2010, their tumultuous on-again, off-again relationship lasting for years. During one of their off periods, Bieber dated model Hailey Baldwin, but this only went on for about one month before he eventually reunited with Gomez. After permanently splitting from Gomez in March 2018, Bieber rekindled his flame with Baldwin and married her within a few months. Gomez seemed to address this quick turnaround in her 2019 single “Lose You to Love Me.” Although Gomez moved on to other relationships, fans continued to speculate about a feud between her and Baldwin. However, both women dispelled those rumors after being photographed together in 2022.

The relationship between Tristan Thompson and Khloé Kardashian has been mired in controversy from the very beginning. In 2018, Thompson confessed to cheating on Kardashian while she was pregnant with their first child. The following year, reports emerged alleging another instance of infidelity, this time with Jordyn Woods, the best friend of Kardashian’s younger sister Kylie Jenner. This revelation sparked a huge scandal, leading to Woods moving out of Jenner’s house, where she had been living. Shortly after, Woods appeared on “Red Table Talk” to apologize and take responsibility for the incident, although she maintained that her interaction with Thompson was limited to a kiss, which he initiated. By 2023, Woods appeared to have reconciled with Jenner.

Before his untimely death in 1997, Biggie Smalls was married once, to singer Faith Evans. The pair tied the knot in 1994, just eight days after meeting at a photoshoot. However, their marriage was plagued by reports of Biggie’s infidelity, including with his protégé Lil’ Kim, whom he first encountered in 1993. Evans and Lil’ Kim reportedly got into multiple physical altercations over this affair, with one incident involving Lil’ Kim allegedly pulling a weapon on Evans. Amidst this turmoil, rapper Charli Baltimore entered the picture. Biggie initiated a relationship with Baltimore while still married, and featured her in the music video for his song “Get Money” as a dig at Evans. All three women attended Biggie’s funeral in March 1997.

The 2000s witnessed a scandalous love triangle involving Hollywood A-listers Brad Pitt, Jennifer Aniston and Angelina Jolie. Pitt and Aniston first met in 1998 and exchanged vows in a lavish ceremony two years later. However, their seemingly enduring bond crumbled when Pitt crossed paths with Angelina Jolie while filming their 2005 movie “Mr. & Mrs. Smith.” Despite both denying any affair during filming, Pitt separated from Aniston in January 2005, paving the way for a relationship with Jolie. The news of Pitt and Aniston’s divorce split the public, and spawned “Team Aniston” and “Team Jolie” merchandise. Pitt and Jolie remained together for years before marrying in 2014, but their union dissolved just two years later, sparking a nasty divorce battle.

Lindsey Buckingham and Stevie Nicks were already a couple prior to joining Fleetwood Mac in 1975. While recording the band’s magnum opus “Rumours,” their relationship faced several challenges, resulting in multiple breakups and reconciliations. Some of the songs on the album directly addressed their tumultuous relationship. During this period, Nicks also became romantically involved with the band’s co-founder Mick Fleetwood, which must have made recording sessions quite awkward. Nicks has referred to Fleetwood as one of her “great great loves,” although she acknowledges their relationship was “a doomed thing.” After dating sporadically for about two years, Fleetwood left Nicks and became involved with one of her best friends, Sara Recor, whom he eventually married.

It is arguably the most notorious love triangle in rock ‘n’ roll history. British model Pattie Boyd captivated two of the most influential guitarists of all time, George Harrison, of Beatles fame, and Eric Clapton. Boyd first married Harrison in 1966, two years after they met on the set of the Beatles’ film “A Hard Day's Night.” During their marriage, she caught the eye of Eric Clapton, a close friend and collaborator of Harrison. Despite Clapton’s persistent advances, Boyd initially rejected him. However, as her marriage to Harrison deteriorated in the mid-70s, she eventually reciprocated Clapton’s feelings. Surprisingly, Harrison gave the two his blessing, even jokingly calling Clapton his “husband-in-law” after he married Boyd in 1979.

The on-screen chemistry between Hollywood legends Spencer Tracy and Katharine Hepburn was so intense that they starred in nine films together. That chemistry apparently lingered even when the cameras were off. However, Tracy and Hepburn couldn’t officially be together as he was married to Louise Treadwell. The pair tied the knot in 1923 and welcomed two children, but their marital problems only grew as Tracy’s career blossomed. He and Hepburn began an affair that was an open secret in Hollywood, though they never acknowledged it. Through it all, Tracy remained married to Treadwell, as California law at the time did not permit no-fault divorce. It was only after Tracy and Treadwell had died that Hepburn publicly acknowledged the affair.

Then the Prince of Wales, Charles married Diana in a fairytale wedding on July 29th 1981. But behind the scenes, his heart belonged to another: Camilla Parker-Bowles. Charles had history with Camilla; the two had dated in the early 1970s, but couldn’t marry as she was deemed unsuitable for a future king. She eventually married Andrew Parker-Bowles, while Charles moved on with Diana. Nevertheless, Charles continued seeing Camilla, which led to Diana's famous remark on their marriage. Unable to reconcile their many differences, Charles and Diana divorced in 1996, and Diana tragically passed away the following year. Camilla remained a close confidante to Charles throughout this period, eventually tying the knot with him in 2005.

Eddie Fisher got married to actress Debbie Reynolds in 1955, after first meeting as teenagers. The two shared a close bond with another celebrity couple: Elizabeth Taylor and Mike Todd, even serving as best man and maid of honor at Taylor and Todd’s wedding. Tragedy struck in 1958 when Todd died in a plane crash en route to New York. Fisher was quick to offer comfort, but he turned into more than just a shoulder to cry on. The two began a scandalous affair that led to Fisher’s hasty divorce from Reynolds. Remarkably, he married Taylor on the same day his divorce was finalized. The media frenzy was relentless, but their union only lasted five years before it, too, crumbled.

Did we miss any other messy celebrity love triangles? Untangle them in the comments below.