19 Dramatic Celebrity Love Triangles, Ranked By Messiness

19 Dramatic Celebrity Love Triangles, Ranked By Messiness

Kaitlynn Boot
Updated October 1, 2025 130.8K views 19 items

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Vote up the most scandalous love triangles that prove dating is messy, even for the stars.

Celebrity drama will always stoke the fires of public curiosity, with messy romantic entanglements and celebrity love triangles topping the list. No one knows the truth of a relationship better than the people inside of it, famous or not. But that doesn't stop humans from being captivated by the speculative details regarding all of the jilted lovers, broken engagements, and infamous cheating scandals that come out of Hollywood. 

Some celebrities have overcome these scandals and stuck with their partners, while others spend years in on-again, off-again relationships as a result of one party's romantic indiscretions. Some celebrity love triangles dominate the news cycle for weeks, like the drama between Ariana Grande, Ethan Slater, and their ex-partners. Others, like the love triangle between Brad Pitt, Angelina Jolie, and Jennifer Aniston, or Elizabeth Taylor, Debbie Reynolds, and Eddie Fisher in the '50s, shake the public to their core, resulting in decisive opinions on who is right, who is wrong, and who is a lying, backstabbing cheater.  

Over 1.8K Ranker voters have come together to rank this list of 19 Dramatic Celebrity Love Triangles, Ranked By Messiness
This list is dynamically ranked based on user voting. The order reflects the consensus of our voters and is not influenced by paid placements or editorial bias.

  • The love triangle between Eddie Fisher, Debbie Reynolds, and Elizabeth Taylor was one of the first to rock Hollywood to its core and is also one of its most notorious. Reynolds and Taylor were friends who met on the MGM studio lot as teenagers. When Reynolds met Fisher overseas entertaining troops stationed in Korea, the two were smitten. They married in 1955 and had two children.

    The couple remained close friends with Taylor and her soon-to-be husband, director Mike Todd, even serving as best man and matron of honor in their wedding. When Todd died in a plane crash in 1958, Fisher traveled to New Mexico to be with Taylor. Less than a month later, he filed for divorce from Reynolds to be with Taylor. 

    In his 2018 memoir, Fisher and Reynolds’s son Todd Fisher wrote about the scandal:

    The world was stunned. Eddie and Elizabeth were vilified. Eddie was declared a philandering, opportunistic loser, and Elizabeth was labeled a bad-girl, home-wrecking slut. Debbie, the good girl, the innocent, unsuspecting victim and single mom, was globally embraced with love and sympathy. 

    Taylor and Fisher’s relationship lasted until 1964, and each would go on to marry and divorce a handful of other famous A-listers of the time, including Richard Burton. Eventually, Taylor and Reynolds were able to rebuild their friendship. Although the divorce wounded Reynolds, she would say little about the whole affair throughout her life. She reportedly did not hold it against Taylor, saying:

    I never felt bitter about Elizabeth. A man doesn’t leave a woman for another woman unless he wants to go. You know, when Mike Todd died, I sent Eddie to help Elizabeth. I don’t think she ever really loved Eddie. He was an interim interest during her mourning period.

    1,110 votes
    What a mess?
  • When 44-year old actor Billy Bob Thornton married his former co-star Angelina Jolie in 2000, no one was more surprised than his fiancee, actor Laura Dern. Dern and Thornton had been together for two years and were planning their wedding when Dern left to film a movie. According to her, she never heard from Thornton again:

    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. It’s like a sudden death. For no one has there been any closure or clarity.

    Jolie and Thornton wed in a surprise Las Vegas ceremony and were together until 2003. During their marriage, the pair shocked the public with couples tattoos and wearing each other’s blood around their necks. For his part, Thornton has never admitted wrongdoing or publicly apologized to Dern for the way their relationship ended, saying only: 

    Others may say that you left our girl and married someone else. But it made me happy and somebody else happy. I’m sorry it caused pain.

    1,743 votes
    What a mess?
  • From 1998 to 2005, actors Brad Pitt and Jennifer Aniston were America’s golden couple. Both were successful actors pursuing creative projects that fans and studios alike were excited about. It seemed like the type of romantic fairy tale Hollywood was built on. 

    In 2005, Pitt starred alongside actor Angelina Jolie in the action thriller Mr. and Mrs. Smith. Rumors spread like wildfire about the pair, speculation that proved valid when Pitt and Aniston announced their divorce in January 2005. A couple of months later, Pitt was photographed on a beach with Jolie, having left Aniston for her. Jolie told Vogue in 2006:

    Brad was a huge surprise to me… Because of the film, we ended up being brought together to do all these crazy things, and I think we found this strange friendship and partnership that kind of just suddenly happened.

    The contentious love triangle and endless tabloid coverage split the country in two, with people taking placing themselves on Team Aniston or Team Jolie.

    Pitt and Jolie married in 2014 and focused on their careers and raising a family, but would go on to divorce in 2016. Allegations of abuse, FBI investigations, and endless custody and legal battles have since taken the internet by storm. Currently, the couple are fighting a legal battle over a French winery they owned together during their relationship.

    Aniston has had a successful acting career in the years since the breakup and spoken out about the way society paints women into a corner where only marriage and motherhood can bring fulfillment. In a 2016 guest column for HuffPost, Aniston wrote: 

    The sheer amount of resources being spent right now by press trying to simply uncover whether or not I am pregnant (for the bajillionth time... but who’s counting) points to the perpetuation of this notion that women are somehow incomplete, unsuccessful, or unhappy if they’re not married with children.

    1,392 votes
    What a mess?
  • The love triangle between reality TV star Brandi Glanville, actor Eddie Cibrian, and country singer LeAnn Rimes was one for the Hollywood history books. 

    In 2008, a video surfaced of Cibrian and Rimes enjoying a romantic dinner together. The pair had grown close while filming their movie Northern Lights but denied having an affair. At the time, Glanville and Cibrian had been married for seven years and had two children, and Rimes had been married to her husband of six years, Dean Sheremet.

    When news of the affair finally broke, Glanville and Cibrian reportedly attended couples counseling in an effort to resolve their issues and save their marriage. Despite this, Cibrian did not stop seeing Rimes, who officially separated from her husband in 2009. Glanville filed for divorce in 2010. Both parties would release public statements about the situation and traded taunts back and forth, creating plenty of fodder for tabloid headlines. Glanville later said:

    I couldn't turn on the TV without seeing something about them. LeAnn had taken over my life and I didn't have a voice anymore… 

    [After seeing her son sit in Rimes's lap] I had this rage in my body. I really wanted to kill her. I walked over to her, grabbed Jake and I looked at her and said, “I will f*cking murder you.” I didn't cope well. I was angry, I was drinking - chardonnay was my crutch. I was so mad at Eddie for blowing up our life together.

    The feud finally seemed to come to an end in April 2018 with an Instagram post from Glanville announcing the trio had finally buried the hatchet and were moving forward. In an interview with People, she said: 

    We just kind of had it out about what is right, what is wrong, what’s better for the kids, and what bothered me and what bothered her.

    969 votes
    What a mess?
  • Twilight fans rejoiced when the franchise’s lead actors, Kristen Stewart and Robert Pattinson, became an item in real life. The co-stars began dating in 2008, although they initially kept their relationship quiet. According to Stewart, falling in love with Pattinson was inevitable:

    We were together for years. I was super in love with my high school boyfriend. But me and Rob were a little older and it was just like, gu-gung.

    In 2012, however, scandal hit after Stewart was photographed kissing the married director of her film Snow White and the Huntsman, Rupert Sanders. Stewart made a public apology for what she called a “momentary indiscretion” that mentioned Pattinson specifically, saying, “I love him, I love him, I'm so sorry.” 

    The pair attempted to reconcile but were ultimately unsuccessful. Each moved on to pursue different relationships and acting projects in 2013.

    Sanders also issued an apology to his wife, Liberty Ross, who had portrayed Stewart's mother in the film. In response to the news, she posted an image of drunken Snow White with the words “Not so pretty and pure anymore." The pair ultimately divorced.

    725 votes
    What a mess?
  • Actors Meg Ryan and Dennis Quaid met on the set of Innerspace in 1987 and quickly became America’s favorite couple. They married in 1991 and divorced 10 years later. Ryan’s mega stardom and Quaid’s infidelity would later be cited as reasons for their painful breakup, but at the time all any tabloid could focus on was the potential infidelity between Ryan and co-star Russell Crowe, who dated briefly post-divorce. Ryan would go on to express her belief that Crowe was unfairly blamed for her and Quaid’s separation:

    I think he took a big hit. But Russell didn’t break up the marriage. He was definitely there at the end, but it wasn’t his fault. I was a mess. I hurt him, too, at the end. I couldn’t be in another long relationship; it wasn’t the time for that. So I got out.

    Her later allegations that Quaid was unfaithful during their marriage and that they had a bad marriage caused Quaid to respond. In an interview with the New York Daily News, he said:

    It was eight years ago, and I find it unbelievable that Meg continues publicly to rehash and rewrite the story of our relationship. Also, I find it regrettable that our son, Jack, has to be reminded in a public way of the turmoil and pain that every child feels in a divorce.

    833 votes
    What a mess?