Although your favorite celebrity couples may seem like the perfect match now, some have endured rocky roads before finding their happily ever after.
In honor of “National Text your Ex” day on October 30 – a holiday you may not know existed – we are taking a look at some of Hollywood’s most tumultuous relationships, where the couples have broken up only to reconcile, sometimes decades later.
PRINCE WILLIAM AND KATE MIDDLETON
Once upon a time a royal and a commoner fell in love. At first Prince William and Kate Middleton were merely peers at the University of St. Andrews, but eventually, the two began dating after moving in together along with some other friends.
The couple was frequently photographed on outings together, often with William’s brother, Prince Harry. They dated for several years, until the spring of 2007 when it all changed.
Suddenly, the prince was an eligible bachelor, and Middleton was a woman on the rebound. Rumors swirled that she dated one of William’s best friends during their brief split, but the couple would quickly reunite.
By 2010, William and Middleton were engaged. In an interview with ITV after the announcement, William confirmed that they had previously broken up, but gave a different timeline. “We did split up for a bit. But that was just – we were both very young, it was at university… We were both sort of finding ourselves and such and being different characters and stuff. It was very much trying to find our own way, and we were growing up… It was a bit of space.”
“At the time, I wasn’t very happy about it, but actually, it made me a stronger person,” MIddleton added.
The couple married five months later in April 2011. They have since gone on to have three children together: Prince George, Princess Charlotte and Prince Louis.
ORLANDO BLOOM AND KATY PERRY
During the “American Idol” season premiere in 2016, Katy Perry confirmed she had met Orlando Bloom at an awards show in January 2016. “We were at the Golden Globes and we weren’t together… My security guard grabbed 10 In-N-Out’s and all of a sudden, I see my boyfriend’s hand – he wasn’t even sitting at our table, he just swoops in and he grabs it, and I’m like, ‘Hey, that’s my burger.’”
The couple reunited at a party, going Instagram official in May, but later split in 2017.
Representatives for both individuals told People magazine, “Before rumors or falsifications get out of hand, we can confirm that Orlando and Katy are taking respectful, loving space at this time.”
The couple maintained a friendship and were even spotted on vacation together in 2018. In September, they confirmed their romance was back on at the Gala for the Global Ocean at the Opera of Monte-Carlo in Monaco. In February 2019, the couple shared that they were engaged. Perry told Jimmy Kimmel that the “Pirates of the Caribbean” actor popped the question on Valentine’s Day.
The following year, still engaged, the couple announced they were expecting their first child together. They would reportedly postpone their nuptials due to the COVID-19 pandemic later that year. In August 2020, they welcomed their daughter Daisy Love.
JESSICA BIEL AND JUSTIN TIMBERLAKE
By 2007, Justin Timberlake had dated a bevy of beautiful women. After his breakup with actress Cameron Diaz, he was spotted out with Jessica Biel. She had recently split with baseball great Derek Jeter.
The couple dated for several years, maintaining a very private relationship, although they were spotted out in public on many instances.
In March 2011, representatives for the stars addressed rumors that the couple had split. “Addressing the media speculation regarding Jessica Biel and Justin Timberlake’s relationship, we are confirming that they mutually have decided to part ways. The two remain friends and continue to hold the highest level of love and respect for each other,” they stated to People.
Months later, Timberlake was still singing Biel’s praises, telling Vanity Fair that Biel “is the single-handedly most significant person in my life.”
“In my 30 years, she is the most special person, okay? I don’t want to say much more, because I have to protect things that are dear to me—for instance, her.”
Their breakup did not last long. By December, the couple was engaged. In October the following year, they married in Italy. The couple have two sons together: Silas and Phineas.
JUSTIN BIEBER AND HAILEY BALDWIN
For a long time, Justin Bieber had an on-off relationship with Selena Gomez. During one break in their relationship, he started hanging out with model Hailey Baldwin, whom he had met several years prior when he was just beginning his career.
The two first sparked dating rumors in 2014; however, Hailey shot down rumors they were together. “I’ve known him since I was so young—since I was like 13—and we’ve just been good friends over the year and we have just stayed close. And there’s nothing more to it than that,” she told E! News.
Fast-forward a year, and another brief bout of romance with Gomez, Bieber confirmed he and Baldwin were more than friends, posting a photo of the two kissing on New Year’s Eve. A few months later, they both separately confirmed that they were not officially dating, mainly due to past relationship mistakes and busy schedules.
Bieber told GQ Magazine in March 2016 that Baldwin was “someone I really love. We spend a lot of time together.”
Reflecting on his past, and perhaps peeking into his future, Bieber said, “I know that in the past I’ve hurt people and said things that I didn’t mean to make them happy in the moment. So now I’m just more so looking at the future, making sure I’m not damaging them. What if Hailey ends up being the girl I’m gonna marry, right? If I rush into anything, if I damage her, then it’s always gonna be damaged. It’s really hard to fix wounds like that. It’s so hard.… I just don’t want to hurt her.”
The couple would not last, and in a Vogue cover story done when the couple was later married, Baldwin confirmed their split during that time was dramatic. “‘Fizzled’ would not be the right word — it was more like a very dramatic excommunication,” Baldwin noted. “There was a period where if I walked into a room, he would walk out.”
After another reconciliation with Gomez, Bieber finally called that relationship quits in 2018 and reunited with Baldwin.
They dated for only a month before they were engaged in July, marrying in a civil service that September. The couple had a more elaborate wedding in South Carolina in 2019 and have been married ever since.
BEN AFFLECK AND JENNIFER LOPEZ
Ben Affleck and Jennifer Lopez’s relationship goes way back to the early 2000’s. When the couple met on the set of their film “Gigli,” Lopez was married to second husband Cris Judd. She filed for divorce in June 2002 and was engaged to Affleck by November.
They were supposed to marry in September 2003, but days before their big day, they told the press “excessive media attention” had led to the postponement of their wedding. By February 2004, the couple had split.
Affleck went on to marry actress Jennifer Garner, while Lopez went on to marry singer Marc Anthony. Despite their very public breakup, they remained cordial and spoke highly of one another in the media.
Lopez dated former baseball player Alex Rodriguez for several years, with the two getting engaged. They called things off in 2021, and months later, Affleck was reportedly seen visiting Lopez. Throughout the summer, they were photographed on multiple occasions looking like a couple.
In July 2021, their relationship was seemingly confirmed when Lopez’s friend Leah Remini posted a video, which included images of the couple in a photo booth. Later that month, JLo shared a picture of the couple kissing to Instagram.
Things progressed naturally for the reconciled couple, becoming engaged in April 2022. They married in a Las Vegas church in July and held a star-studded ceremony in Georgia in August.