For many of us, the road to everlasting love is littered with former flames, and the rich and famous are no different. While stars like Ryan Reynolds and Blake Lively are happily married now, it can be easy to forget they’ve left a string of very noteworthy exes in their wake.
From Jennifer Aniston and Brad Pitt to Prince Harry and Cressida Bonas, let’s take a trip down memory lane and look back on the ones who got away.
© GettyJennifer Aniston and Brad Pitt
Jennifer Aniston is happily in a relationship with wellness coach and hypnotist Jim Curtis, but in the minds of many, she will be forever linked with her most famous ex: Brad Pitt.
The Friends actress, 57, and the Hollywood heartthrob, 62, began dating in 1998 after Brad split from Gwyneth Paltrow and Jennifer broke up with actor Ted Donovan.
They married in an extravagant ceremony in Malibu two years later and enjoyed five years of matrimony before it all came crumbling down.
The couple announced their separation in January 2005, which came after months of speculation that Brad had grown close to his Mr. & Mrs. Smith co-star Angelina Jolie. Their divorce was finalised in October 2005.
Brad subsequently married Angelina, 50, adopting three children with her and having three more while Jennifer married Justin Theroux. Both marriages ended in divorce.
Jennifer and Jim, 50, were introduced through mutual friends and were friendly for a while before things turned romantic.
Romance rumours swirled in June 2025 when the pair enjoyed a getaway to Big Sur, California, and Jennifer went Instagram official with Jim in November when she shared a photo with her arms wrapped around him and wrote: ‘Happy birthday my love. Cherished.’
© Getty ImagesRyan Reynolds and Scarlett Johansson
Given he will be celebrating his fourteenth wedding anniversary with Blake Lively in September, it’s easy to forget Ryan Reynolds was previously married to another Hollywood starlet.
The Deadpool actor, 49, began dating Scarlett Johansson, 41, in April 2007, shortly after his breakup from singer and fellow Canadian, Alanis Morissette.
It was a whirlwind romance for the actors who announced their engagement in May 2008 before marrying that September.
They announced their separation only two years later, however, and their divorce was finalised in July 2011.
Scarlett is now married to Saturday Night Live star Colin Jost. The couple are parents to 4-year-old son Cosmo and she is also mother to 11-year-old Rose with her ex, Romain Dauriac.
Ryan and Blake, 39, are parents to James, 11, Inez, nine, Betty, six, and Olin, three.
Sienna Miller and Jude Law
Sienna Miller, 44, and Jude Law, 53, were one of the most iconic couples of the noughties.
They first met on the set of the 2004 film Alfie and were engaged on Christmas Day of the same year. At the time, their spokesperson told People magazine: "They are spectacularly happy. He proposed to her on Christmas Day with a gold band and nine diamonds."
But the happy times were short-lived as Sienna and Jude’s relationship imploded in May 2005 when it emerged he had had an affair with his children’s nanny.
At the time, he released a statement to the papers which read: "Following the reports in today's papers, I just want to say I am deeply ashamed and upset that I've hurt Sienna and the people most close to us. I want to publicly apologise to Sienna and our respective families for the pain that I have caused. There is no defence for my actions which I sincerely regret and I ask that you respect our privacy at this very difficult time."
The pair tried to make it work but they eventually split in November 2006 before reconciling in 2009 and splitting for good in 2011.
From 2011 to 2015, Sienna dated and became engaged to actor Tom Sturridge with whom she shares daughter Marlowe, 13.
The actress has been dating actor Oli Green, 29, since late 2021. They had a daughter in December 2023 and Sienna gave birth to her third child in April 2026.
© Getty ImagesAshton Kutcher and Demi Moore
Ashton Kutcher, 48, began dating Demi Moore, 63, in 2003, with their 15-year age gap raising eyebrows at the time.
The pair married in September 2005 and were together for six years before announcing their separation in November 2011. Their divorce was finalised two years later.
In a statement, Ashton said: "I will forever cherish the time I spent with Demi. Marriage is one of the most difficult things in the world and unfortunately sometimes they fail.”
Demi wrote about their relationship in her 2019 memoir Inside Out where she discussed Ashton’s alleged infidelity and the toll the relationship took on her health.
Punk’d star Ashton officially began dating Mila Kunis, 42, in 2012, years after they met as co-stars on That ‘70s Show.
They got engaged in 2014 and married the following year and are parents to Wyatt, 11, and Dimitri, nine.
© WireImagePrince Harry and Cressida Bonas
Prince Harry enjoyed a string of romances before settling down with Meghan, but his romance with Cressida Bonas was the most memorable.
The Duke of Sussex, 41, and the model, 37, began dating in 2012 after they were introduced by Harry’s cousin, Princess Eugenie.
But as rumours of a royal engagement escalated, Cressida is said to have become increasingly overwhelmed by the public attention.
Harry eventually ended their relationship in 2014 and wrote in his 2023 memoir Spare that Cressida was ‘always clear about not wanting to take on the stresses of being a royal’.
The former couple have remained friends however, and Cressida was in attendance at Harry and Meghan’s wedding in 2018.
