In the glitzy world of fame and flashing cameras, love stories are rarely simple. Hollywood has long been a hotspot for whirlwind romances, shocking betrayals, and tangled love triangles that dominate headlines and spark endless fan theories. Some stars fall in love on set, only to find their relationships tested by fame, temptation, or secret flings.
1. Brad Pitt, Jennifer Aniston, and Angelina Jolie
Perhaps the most iconic love triangle in modern Hollywood history, the saga between Brad Pitt, Jennifer Aniston, and Angelina Jolie is still talked about nearly two decades later. Brad and Jennifer were the golden couple of the early 2000s—married in 2000, they were America’s sweethearts.
But things began to unravel in 2005 when Brad starred opposite Angelina Jolie in Mr. & Mrs. Smith. Their onscreen chemistry sparked rumors, and by the end of the year, Brad and Jennifer had finalized their divorce. Although Brad and Angelina denied any wrongdoing at the time, the public narrative was set: Angie had “stolen” Brad.
The two eventually became Brangelina, raising six children before their own split in 2016, closing the book on one of Hollywood’s most infamous love triangles.
2. Kylie Jenner, Tyga, and Blac Chyna
The Kardashian-Jenner clan is no stranger to drama, but few relationships stirred as much chaos as the tangled web involving Kylie Jenner, rapper Tyga, and model Blac Chyna. Tyga and Chyna were once engaged and share a child, King Cairo. But not long after they broke up, Tyga was seen getting close to Kylie—who was still a teenager at the time.
Blac Chyna was vocal about her displeasure, and tensions escalated when she began dating Kylie’s brother, Rob Kardashian, seemingly out of revenge. Chyna and Rob even had a daughter, Dream, together before their relationship imploded on social media in a haze of accusations, lawsuits, and public breakdowns. This tangled triangle blurred the lines between love, revenge, and reality TV ratings.
3. Tristan Thompson, Khloé Kardashian, and Jordyn Woods
Speaking of Kardashian chaos, Khloé Kardashian’s relationship with NBA player Tristan Thompson has been a rollercoaster in itself. The couple started dating in 2016 and welcomed daughter True in 2018. However, Tristan’s repeated cheating scandals became the defining feature of their on-and-off romance.
The most shocking betrayal came in 2019 when reports surfaced that Tristan had kissed Jordyn Woods—Kylie Jenner’s best friend—at a party. The fallout was swift and severe.
Jordyn was publicly iced out by the Kardashian-Jenners, and Khloé and Tristan called it quits. Though the two later attempted to co-parent and reconcile, more scandals followed, including news that Tristan had fathered another child with a different woman during their reconciliation. Messy doesn’t even begin to describe it.
4. Kristen Stewart, Robert Pattinson, and Rupert Sanders
Fans of the Twilight saga lived for the offscreen romance between stars Kristen Stewart and Robert Pattinson. Their real-life relationship added a layer of magic to their vampire-love fantasy, but everything fell apart in 2012 when photos surfaced of Kristen kissing Snow White and the Huntsman director Rupert Sanders—who was married at the time.
The scandal blew up overnight. Kristen issued a public apology to Rob, while Rupert’s marriage eventually fell apart. Though Rob and Kristen attempted to move past the betrayal, their relationship never fully recovered. The affair not only ended one of young Hollywood’s favorite romances but also fractured multiple relationships in the process.
5. Justin Bieber, Selena Gomez, and Hailey Baldwin
Justin Bieber and Selena Gomez were the poster couple for young love in the 2010s. Their on-again, off-again relationship spanned years and inspired songs, fan pages, and public meltdowns. But the drama escalated in 2018 when Justin and Selena split—seemingly for good—and he quickly rekindled things with Hailey Baldwin.
Within months, Justin and Hailey were married, leaving Jelena fans shocked and heartbroken. Speculation ran wild over whether there was overlap in his relationships, especially since Selena and Justin had only recently vacationed together.
The triangle continues to live on through song lyrics, social media shade, and devoted fan camps on either side.
6. Miley Cyrus, Liam Hemsworth, and Kaitlynn Carter
Miley Cyrus and Liam Hemsworth had one of the most unpredictable love stories in Hollywood. After nearly a decade of ups and downs, the pair finally married in 2018—only to announce their split less than a year later.
Just days after the announcement, Miley was photographed kissing Kaitlynn Carter, Brody Jenner’s ex-wife, on a yacht in Italy. The sudden PDA set off headlines worldwide and had fans questioning the timeline of events.
While Miley maintained that her relationship with Kaitlynn began after her split from Liam, the quick transition led to plenty of speculation—and more than a little chaos.
7. Olivia Rodrigo, Joshua Bassett, and Sabrina Carpenter
The world of Disney stars collided in dramatic fashion when High School Musical: The Musical: The Series co-stars Olivia Rodrigo and Joshua Bassett reportedly dated—and then broke up in the public eye.
Fans read between the lines of Olivia’s breakout hit “drivers license,” which alluded to a “blonde girl” who was “everything I’m insecure about”—widely believed to be singer and actress Sabrina Carpenter.
Joshua and Sabrina were soon seen together, prompting rumors of a love triangle. All three stars remained somewhat cryptic, but the drama fueled several hit songs and one of Gen Z’s most memorable musical feuds. The emotional fallout and cryptic lyrics made this triangle an instant pop culture moment.
8. Meg Ryan, Dennis Quaid, and Russell Crowe
In the late ’90s, Meg Ryan and Dennis Quaid were one of Hollywood’s most admired couples, married for nearly a decade. But their fairytale ended when Meg began a brief but headline-making affair with her Proof of Life co-star Russell Crowe in 2000.
While the media painted Meg as the villain, she later revealed that her marriage with Dennis had already been struggling due to his own infidelities.
Nonetheless, the affair overshadowed her career at the time, and her relationship with Crowe fizzled out soon after. The scandal was a reminder that even the most wholesome-seeming stars could be caught in messy love triangles.
Celebrity relationships are often fast-paced, passionate, and painfully public. When love triangles and affairs get added into the mix, things quickly spiral into full-blown scandals.
As long as Hollywood remains the land of beautiful people and bigger-than-life drama, messy love triangles will be part of the narrative. And honestly, whether we love to hate them or hate to love them, we’ll keep watching.
