Oh, Hollywood, the land of failed relationships. We hate to admit it, but we love seeing celebrity couples fall in love, especially if it’s two people we admire. Sometimes we’re upset when we see these relationships come to an end, and other times we’re secretly hoping it won’t work out for them. Even though most of the time we expect it, it still comes as a surprise when we find out that these famous couples decided against taking that trip down the aisle.
A broken engagement is not a common occurrence in the real world, that’s why we love hearing about celebrities that choose to return their big diamond rings. Some of the couples on this list are more unexpected than others; some seemed like the perfect couple while others will make you question why they were ever together in the first place. You never know, there may be hope for these lovebirds in the future, although we doubt Bennifer will be reconciling anytime soon. Here are 12 celebrity couples who called off their wedding.
12 Emma Roberts and Evan Peters
Actors Emma Roberts and Evan Peters met on the set of the film Adult World in 2012. A year later the pair got engaged during the winter holidays, when Roberts was only twenty-two years old and Peters was twenty-six. Not only were they together at home, they were also together at work, both starring on the television shows American Horror Story: Coven and American Horror Story: Freakshow. In the summer after their engagement, Roberts was arrested after punching her fiancée in the nose while visiting him in Montreal. After the incident, fans were expecting a breakup. The split finally happened in 2015.
11 Sean Penn and Charlize Theron
In 2013, two of Hollywood’s biggest stars, Sean Penn and Chalize Theron, announced that they were in a relationship and soon after they were secretly engaged in Paris. Penn has been through two very messy divorces beforehand. Even though there was a fifteen-year age difference between them, they seemed super smitten with one another. Just recently, Theron gushed to Esquire magazine “I’m a very, very, very lucky girl. Very lucky. He’s hot.” We guess physical attraction isn’t everything, seeing as how Penn and Theron decided to end things in June of 2015.
10 Kiefer Sutherland and Julia Roberts
Kiefer Sutherland and Julia Roberts began dating in 1990 and a year later they were all set to walk down the aisle. Everything was ready for the ceremony when Roberts pulled a real-life Runaway Bride and shut the whole thing down only a few days before the wedding date. There were rumors that Sutherland was caught having an affair with a stripper and it was reported that Roberts ran off with another actor, but family, friends, and fans were upset that the high-profile relationship came to an end, regardless of why it ended.
9 Edward Norton and Courtney Love
Courtney Love’s most notorious relationship is with the late and great Kurt Cobain, but he wasn’t the only man she ever loved. After starring in the film The People vs. Larry Flint together in 1996, Love and actor Edward Norton dated on and off for a few years. Norton proposed to Love, but the engagement was called off when she decided to leave him for another man. Norton went on to become an A-list actor, and Courtney has said she regrets leaving him back in the day, saying “I should have married Edward” and “I have the greatest respect for Edward. He could be president of the United States.”
8 Jude Law and Sienna Miller
Jude Law and Sienna Miller seemed like the perfect couple. Both are talented, attractive, and English. They were engaged in 2004, but in 2005 Law was caught having an affair with the nanny of his children from a prior marriage. It was also reported that Miller was cheating on Law at the same time, sleeping with his good friend and James Bond himself, Daniel Craig. The couple attempted to reconcile, but split up again in 2006 for good. This time it was allegedly due to her messy dogs and the fact that he didn’t want to party as often as she did.
7 Ben Affleck and Jennifer Lopez
Ben Affleck and Jennifer Lopez began the celebrity couples name game trend, deemed ‘Bennifer’ by fans and journalists. They were engaged in 2002, Affleck proposed with a 6.1-carat diamond ring. But a day before the wedding in 2003, the pair postponed the ceremony. They blamed the media and paparazzi for the delay, but in reality their relationship was suffering. The wedding never happened, and Affleck began dating Jennifer Garner a few months after his split with Lopez. “It felt like my heart had been torn out of my chest” J.Lo has said about the break-up.
6 Lance Armstrong and Sheryl Crow
Lance Armstrong and Sheryl Crow were together for two years, and were engaged for five-months before calling off their wedding in 2006. Fans were devastated; the two seemed like the epitome of a fit and happy couple. They gave no reason for the split, but in 2009 Armstrong spoke up about the failed relationship, saying “She wanted marriage, she wanted children; and not that I didn’t want that, but I didn’t want that at that time because I had just gotten out of a marriage, I’d just had kids, yet we’re up against her biological clock – that pressure is what cracked it.”
5 Liam Hemsworth and Miley Cyrus
After starring together in the romantic Nicholas Sparks film The Last Song, Liam Hemsworth and Miley Cyrus dated for four years. They were engaged in 2012, when Cyrus was only nineteen years old. But the engagement only lasted a year. There were sexting rumors on Hemworth’s end, and Cyrus’ infamous MTV VMA performance; it was apparent that both stars were too young to be getting married. The singer told Harper’s Bazaar “I definitely don’t have time to deal with a wedding right now.” They split in 2013, after Cyrus unfollowed Hemsworth on Twitter.
4 Brad Pitt and Gwyneth Paltrow
Gwyneth Paltrow was almost ten years younger than Brad Pitt when they began dating in 1995. They dated for three years when Pitt popped the question, and as in love as Paltrow was with one of Hollywood’s hottest actors, she knew she wasn’t ready for that kind of commitment and was scared of settling down in her early twenties. She only has kind words to say about Pitt these days, and claims that when she looks back now she doesn’t know what she was thinking when she broke up with him; “I didn’t know what I was doing.”
3 Deadmau5 and Kat Von D
Deejay Deadmau5 proposed to tattoo artist Kat Von D in 2013 over Twitter, saying “I can’t wait for Christmas so…Katherine Von Drachenberg, will you marry me?” The pair were planning an underwater themed wedding but by 2013 the engagement was called off. Deadmau5 claims he was never unfaithful, but his ex-fiancé tweeted “Cheating on your loved one is the most hurtful thing one could do. I hate to have to admit that this relationship is indeed over…Onwards and upwards.” If nothing else, this break-up proves that important conversations in a relationship should never happen over social media.
2 Johnny Depp and Winona Ryder
In 1989, heartthrobs and A-list celebrities Johnny Depp and Winona Ryder began dating. Two years later, they were engaged. Both were in their mid-twenties and were obsessed with one another. Depp got a tattoo that said ‘Winona Forever’ and they made the much-loved film Edward Scissorhands together. But three years into their engagement, the pair called it off, and Depp got his ink changed to ‘Wino Forever’. It didn’t take the actor long to move on, the same year that he split with Ryder he began dating supermodel Kate Moss.
1 Ryan Reynolds and Alanis Morissette
After four years together, Canadian actor Ryan Reynolds and Canadian songstress Alanis Morissette called off their wedding in 2007. They were engaged for a few years, but never set a wedding date, which was already a bad sign for the couple. The song “Torch” on Morissette’s album Flavours of Entanglement is reportedly about Reynolds. But don’t feel too bad for the actor, he married actress Scarlett Johansson in 2010. After divorcing her a year later he met actress Blake Lively on the set of Green Lantern. The two began dating in 2011 and married in 2012.