18 failed celebrity engagements: Olivia Wilde, Ariana Grande, Zayn Malik and more

We love the excitement of a celebrity engagement, and when things don't turn into a happily ever after it is such a shame. From Olivia Wilde to Ariana Grande, these 18 celebrities have decided to end their relationships before walking down the aisle. Take a look back...

Olivia Wilde and Jason Sudeikis

Olivia Wilde and Jason Sudeikis ended their seven-year engagement in 2020. The pair started dating back in 2011, and the catalyst for the break-up is still unknown. However, they are both keen to focus on co-parenting their children, Otis and Daisy.

Kerry Washington and David Moscow

Scandal star Kerry Washington ended her engagement with David Moscow in 2007 after dating for four years. Kerry has since married NFL star and actor Nnamdi Asomugha – and they like to keep their personal life very private.

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Ariana Grande and Pete Davidson

Dangerous Woman singer Ariana Grande had a whirlwind relationship and engagement to Pete Davidson, following her split from Mac Miller in 2018. The couple started dating in May, and by June they were engaged. But by October, their engagement was over almost as quickly as it began.

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Rob Kardashian and Blac Chyna

Rob Kardashian’s relationship with Blac Chyna wasn’t without its share of drama, given her fraught relationship with the rest of his family. Nonetheless, the couple got engaged after just ten weeks of dating, and welcomed their daughter Dream together in November 2017. But their on-off relationship wasn’t to be; the pair broke off their engagement by February 2018.

Faye Brookes and Gareth Gates

Coronation Street actress Faye Brookes and Gareth Gates have reportedly ended their engagement after a seven-year on-off relationship. The couple announced their engagement in January, and Faye had spoken excitedly about her “epic” wedding plans, revealing they had already asked Holly Willoughby’s sister Kelly to officiate. However, it appears they ultimately decided to call it quits before getting married.

Lady Gaga and Taylor Kinney

Prior to her relationship with Christian Carino, Lady Gaga was engaged to Taylor Kinney. The couple were together for five years and engaged for over a year before calling it quits in 2016.

Gwyneth Paltrow and Brad Pitt

Back in 1996, Brad Pitt proposed to his Seven co-star Gwyneth Paltrow following a two-year relationship. The actor popped the question on the set of Seven Years in Tibet in Argentina, but they broke up just six months later. Brad has since been married to Hollywood stars Jennifer Aniston and Angelina Jolie, while Gwyneth recently tied the knot with Brad Falchuk following her marriage to Coldplay frontman Chris Martin.

Ben Affleck and Jennifer Lopez

She may be excitedly planning her wedding to Alex Rodriguez now, but long before meeting A-Rod, Jennifer Lopez was engaged to Ben Affleck. Then known as Bennifer, the couple got engaged in November 2002 after less than a year of dating, but they called it off in September 2003 just four days before their wedding.

Johnny Depp and Winona Ryder

As well as two marriages, Johnny Depp has been engaged a further three times, including to Stranger Things star Winona Ryder. The pair met at a film premiere and got engaged just five months later, with Johnny even getting a tattoo reading “Winona Forever” in honour of his fiancée. However, the couple split after a three-year engagement, and Johnny changed the tattoo to say “Wino Forever”.

Alanis Morissette and Ryan Reynolds

He’s one half of a Hollywood power couple with Blake Lively now, but back in the early 2000s, Ryan Reynolds was engaged to Alanis Morissette. The couple started dating in 2002 and got engaged two years later, but broke up in 2007. The Deadpool star went on to marry Scarlett Johansson, before settling down with Blake after meeting on the set of Green Lantern.

Chris Klein and Katie Holmes

Chris Klein proposed to Katie Holmes in 2003, following a three-year relationship. The couple were engaged for two years before ending their romance, and it was only a month later that Katie went on her first date with Tom Cruise, with whom she welcomed daughter Suri and went on to marry.

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Jude Law and Sienna Miller

Jude Law and Sienna Miller were the ‘it’ couple of the moment when they started dating in 2004, after starring together in Alfie. The couple got engaged on Christmas Day of that year, and had an on-off relationship after it emerged that Jude had an affair with his children’s nanny, before ending their engagement in November 2006. They reconciled in December 2009, but called it quits for good in February 2011.

Alexandra Burke and Joshua Ginnelly

Former X Factor winner Alexandra Burke is yet to confirm her split from her partner of three years, Joshua Ginnelly, but sparked speculation of a break-up when she removed all trace of him from her social media accounts. Earlier this year, Alexandra told HELLO! that they were putting their wedding plans on hold because they wanted to travel before settling down. However, they appear to have decided to split, and Alexandra has since been linked to footballer Angus MacDonald.

Lady Gaga and Christian Carino

Lady Gaga announced her split from fiancé Christian Carino in February, following a short engagement. The A Star is Born actress started dating Christian in 2017 and got engaged the following year, but their whirlwind romance ended in the middle of awards season in 2019.

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Brie Larson and Alex Greenwald

Captain Marvel actress Brie Larson confirmed in January 2019 that she had ended her engagement to Phantom Planet frontman Alex Greenwald, after around three years. The couple had started dating in 2013, and said they have remained close despite their split.

Mariah Carey and James Packer

Who can forget the incredible 35-carat engagement ring given to Mariah Carey by billionaire businessman James Packer in 2016?! The couple were inseparable throughout their two-year relationship, but broke up in October 2016.

Zayn Malik and Perrie Edwards

The young love between X Factor alumni Zayn Malik and Perrie Edwards lasted from 2012 to 2015, with the couple announcing their engagement in August 2013. Perrie supported Zayn throughout his decision to leave One Direction, but the couple parted ways just a few months later. The Little Mix singer has since revealed that Zayn dumped her via a text message.

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Jesy Nelson and Jake Roche

Perrie’s Little Mix bandmate Jesy Nelson was also engaged to a boyband star – Rixton singer Jake Roche, the son of Coleen Rooney and Shane Richie. The couple got engaged in July 2015 but by December 2016 it was confirmed they had “amicably split”.