Home Features 10 Celeb Couples Who Tried Again – And FAILED

10 Celeb Couples Who Tried Again – And FAILED

These on-again off-again couples didn't work out


Sometimes going back to the one you loved can be the biggest mistake, but these celebrities gave it a try anyway.

While some stars make it work, these 10 celebrity couples just started another car crash relationship.

Take a look:

1. Chris Brown and Rihanna

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Who can forget 2009, the night before the Grammys, when Chris Brown beat up his equally famous girlfriend Rihanna.

One of the biggest celebrity couples in the world at the time, the pair went their separate ways after RiRi filed a police report.

Chris begged to get her back, which didn’t work then, but in 2012 the pair reunited, even releasing some tracks together, including ‘Birthday Cake’.

Chris Brown in court
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In an interview RiRi said she thought she could change him. “I felt that people didn’t understand him,” she told Vanity Fair.

“You want the best for them, but if you remind them of their failures, of if you remind them of bad moments in their life, or even if you say I’m willing to put up with something, they think less of you.”

Of course the pair later split in 2013 for good.

2. Sienna Miller and Jude Law

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Another star couple that gave their romance another try is Sienna Miller and Jude Law.

The pair were engaged back in 2004, but their relationship was rocked in 2005 when it was revealed he was having an affair with his children’s nanny.

To make things even more complicated, Sienna and Jude tried to work things out back then, but then she had an affair with James Bond star Daniel Craig, who was actually friends with Jude.

They split officially in 2006, but cut to 2009, when the pair rekindled their romance once again.

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Pictures surfaced of the pair and Jude’s children in Barbados, and it looked like the couple were back living the dream.

But as usual in Hollywood, nothing is what it seems.

There was a lot of tension between Sienna and Jude’s ex wife Sadie Frost, which made things even more difficult, and then in 2011 the couple split for good.

Even writing this feels emotionally exhausting…

3. Selena Gomez and Justin Bieber

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This rollercoaster relationship is far from over, but right now it looks like these two are split again.

The couple originally got together in 2010 (over pancakes in an iHop), but then the couple had an emotional breakup in 2012.

But just one year later rumours started swirling that Jelena were back on, after Justin shared a selfie on his Instagram with the singer.


In 2014 JB unfollowed Selena on Instagram, but the pair continued to talk about each other in interviews.

Skip to 2017, Selena endured yet another public break up, this time from The Weeknd, and just days later she was spotted with Justin.

The pair seemed to be back on strong, but according to reports the couple are now currently “on a break”.

4. Katy Perry and John Mayer

This set of songbirds were first linked in 2012 when they were seen packing on the PDA at the Soho House in West Hollywood.

While many questioned the pop star’s decision to begin a relationship with Mayer who is famous for his serial-dating, the pair seemed to be getting serious when they spent Christmas together.

They lasted almost a year until March of 2013 when it was revealed that the couple had split.

Their split wasn’t long-lived as they were spotted together again just a few short months later in June.


Adriana M. Barraza/WENN.com

The Gravity singer professed his love for Katy on stage that month, and by August of that summer the pair used their talents to release the duet “Who You Love”.

Katy fueled engagement rumors when she was spotted on multiple occasions wearing a ring on her left ring finger, and sources claimed they wouldn’t be surprised if the happy couple made an announcement.

It came as a shock to many when it was confirmed that the couple split for good in February of 2014.

While the Roar singer has gone on to date celebs like Diplo and Orlando Bloom, Mayer has had a harder time moving on. During press for his 2017 album The Search for Everything, he admitted that “Still Feel Like Your Man” was about Katy.

5. Taylor Swift and Harry Styles

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These A-list musicians met in March of 2012 at the Kid’s Choice Awards, and rumors surrounded the pair for months as they gushed about each other in the press and famous pals like Justin Bieber dropped hints during interviews.

The couple confirmed the rumors in December of that year when they went on a VERY public first date in Central Park.

The relationship moved quickly after that with the couple being constantly spotted together around the world.

They went on dates in Los Angeles, visited Harry’s hometown of Cheshire, vacationed in the Caribbean and went skiing in Utah.

Ivan Nikolov/WENN.com

The couple apparently called it quits in January of 2013 after a fight while on vacation in the British Virgin Islands.

Harry predicted that the country star would release songs about their relationship, as she had done with most of the men she had dated, and he said he was understanding and accepting.

She proved him right when she released “Style” and “Out of the Woods”, which are rumored to both be about him.

Harry was reportedly fixed on the singer and tried to reach out to her to no avail.  He even sent her 1,989 roses, but the pair never ever got back together.

6. Prince Harry and Cressida Bonas

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This royal couple were first introduced in 2012 by Harry’s cousin Princess Eugenie, and were first spotted partying together in London following the premiere of The Dark Knight Rises.

After being spotted out together multiple times and even going on a vacation to Sir Richard Branson’s Necker Island, the pair cooled off when Harry was photographed naked partying, in a Las Vegas.

He was also deployed to Afghanistan for a 20 week stint as a copilot for an Apache helicopter.

The pair rekindled their relationship when he returned, and the couple was spotted together cuddling and kissing in the Swiss alps.

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Back in England, they were spotted at multiple concerts, restaurants and theaters, but didn’t make their official royal appearance until Cressida accompanied Harry to the launch of the WE Day UK young people’s charity event in March of 2014.

Rumors circulated that Harry was going to pop the question to Cressida. However, By April of that year the couple announced their split, but claimed they were remaining friends.

Even though they’re over, Cressida is rumoured to be attending his wedding to Meghan Markle next month.

7. James Middleton and Donna Air

Celebrities attend British Heart Foundation Roll Out The Red Ball at Park Lane Hotel. London. UK

The brother of the Duchess of Cambridge Kate Middleton first started dating Donna Air in 2013, when they were spotted arm and arm at parties and social events around London.

They made the rounds being photographed on countless red carpets, and despite claims that the pair separated in 2015, James insisted that they remained very much together.

The pair did take a break when James briefly moved to Hong Kong to pursue business opportunities for his start up company.

Split: Donna and James are over

Their relationship restarted when he returned, and within a few months breakup rumors started to swirl around the couple again.

These reports were proven to just be rumors as the pair continued to be seen together, with James supporting Donna at her performance for Dancing on Ice.

The couple finally called it quits for good over December of 2017 as Donna confirmed the news in February.

8. Kylie Jenner and Tyga

Tyga and Kylie | INSTAGRAM

One of the most famous on and off couples, Kylie Jenner and Tyga first met when Tyga performed at Kendall Jenner’s Sweet 16, when Kylie was just 14 years old.

Reconnecting a few years later, Tyga was seen at Kylie’s 17th birthday party only two days before he ended his engagement to finance and baby mama Blac Chyna.

Controversy followed the couple as the age difference and baby mama drama caused issues between the reality star and rapper, but proved their love when it’s discussed in episodes of Keeping Up With the Kardashians and I Am Kait.

After going public with their love and appearing inseparable, the pair separated around Tyga’s 26th birthday over something he did, but the split didn’t last long as days later they attended the AMA’s together.

after party

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The two walked the Met Gala red carpet separately in May 2016, but by June the pair were spotted back together again.

By March of 2017, the couple split shortly after Blac Chyna blasted Tyga for not paying child support, and made accusations of Tyga cheated on Kylie.

The breakup was for good this time, as Kylie quickly moved on with Travis Scott who she now has a child with, and Tyga moved on with Kylie Jenner lookalike, Demi Rose.

WangSquad @alexanderwangny

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9. Brooklyn Beckham and Chloë Grace Moretz

The young actress met the oldest son of Posh and David Beckham in 2014 at Paris fashion week.

The pair were photographed the following summer and Chloe blushed when asked about the relationship on Watch What Happens Live with Andy Cohen.

A year went by and most assumed that the relationship between the two were over as Brooklyn went back to school and Chloe was busy filming.

After being seen out in London around the holidays, by April of 2016 the couple confirmed their relationship was back on in an Instagram post.

My valentine 🌷

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The pair reportedly got into a fight at a Coldplay concert in September of 2016 that was so bad it ended their relationship.

The break didn’t last long as the couple got back together by March of 2017.  They confirmed the relationship on social media, constantly gushing about one another on their Instagrams.

Things can change fast though, and they did when Brooklyn was recently pictured locking lips with a Playboy model while getting a new tattoo.

The next day Chloe stepped out without her “B” promise ring that she had been wearing during their relationship…OUCH!