This month marks 15 years since her whirlwind engagement to Ashley Cole – the man she vowed she’d “never stop loving” and dubbed her “soul mate”, with whom she planned to start a family of “five kids”.
But her dream came crashing down around her just 18 months after their fairy-tale wedding in July 2006, amid claims the footballer had had sex with hairdresser Aimee Walton after a drunken night out before vomiting on her twice and passing out.
And despite the “disgusted” singer vowing at the time to give him a second chance – insisting, “he’s learning” – their reunion was short-lived when fresh claims emerged 16 months later that Ashley had cheated again with four more women, leaving Cheryl “no choice” but to end their four-year marriage.
Having been left “numb” and “broken” by the split, which initially saw Cheryl’s weight plunge to just 6st, she struggled to move on and admitted they were still in contact after their divorce – and the pair were reportedly spotted kissing at her birthday party the following year amid rumours of a reconciliation. In an emotional interview with Piers Morgan in 2010, she broke down, saying, “I’ll always love Ashley”.
Cheryl, 36, has tried to find love since, but now has a second failed marriage behind her – to restaurateur Jean-Bernard Fernandez-Versini, 39 – which ended in 2016, and her three-year relationship with Liam Payne, with whom she shares son Bear, three, ended in 2018.
Just a month after her split from the former 1D star, Ashley’s pal, fellow ex-footballer Jermaine Pennant, 37 – who was close to the couple during their romance – said, “I think she’s still caught up over Ash. I think that took a toll on her as a person as well. She was madly in love with Ashley and I think her relationships now, after Ash, she’s sort of struggled [with].”
Check out: A look back at Cheryl's dating history from Ashley Cole to Liam Payne
Cheryl relationship timeline - slider with cover pic
Swipe through to see Cheryl's relationship history...
2004-2010: Ashley Cole
Not long into her rise to fame, Cheryl started dating England footballer Ashley Cole, even attending the World Cup with the likes of Victoria Beckham and Coleen Rooney. Clearly smitten, the loved-up pair got married in 2016, penning a six-figure magazine deal at the time.
2004-2010: Ashley Cole
However, things started to turn sour for the 'golden couple' when Ashley was accused of 'cheating' on Cheryl just months after their wedding. Despite forgiving the footballer, Ashley continued with his ways, with allegations that he'd been unfaithful rocking their romance yet again. Everything got too much for Chez in 2010, when she filed for divorce from Ashley.
2010-2011: Derek Hough
Cheryl first met professional dancer Derek Hough whilst the pair filmed the music video for her hit track 'Parachute', and it seems they immediately hit it off. The former X Factor judge contracted Malaria in 2010, and she later told Piers Morgan, "I owe my life to Derek... if it wasn't for him I'd be dead."
2010-2011: Derek Hough
Despite this, it seems the pair were destined to just be friends, with Derek later revealing to the media, "We dated for a while. Absolutely we are still friends, we are still very close."
2012-2013: Tre Holloway
It seems Cheryl had quite a thing for professional dancers, as her next boyfriend was the super handsome Tre Holloway. Despite first meeting each other on The X Factor in 2010, the pair didn't grow close until 2012, with Cheryl enlisting Tre's dancing skills for her 'Ghetto Baby' music video.
2012-2013: Tre Holloway
Things seemed to be getting serious between the two, especially when Tre starred in Cheryl's ITV2 documentary. However, the long-distance relationship didn't work out, with the couple calling it quits in 2013. Speaking at the time, Tre said, "She's an amazing person, an amazing woman, and we are good friends."
2014-2016: Jean-Bernard Fernandez-Versini
It looked like Cheryl had found 'the one' when she met French businessman Jean-Bernard Fernandez-Versini in 2014. Only three months into their romance, Cheryl shocked her fans by announcing she'd married JB, in a secret beach location with her close family and friends.
2014-2016: Jean-Bernard Fernandez-Versini
After her second marriage, rumours of tension between Cheryl and JB started to arise, with the couple being pictured looking glum on more than one occasion. 18 months after their whirlwind wedding, Cheryl and JB were granted a quickie divorce in October 2018.
2016-2018: Liam Payne
Shortly after Cheryl divorced JB, she singer shocked the showbiz world in 2016, when she confirmed she was dating One Direction singer Liam Payne. Despite the pair having a 10-year age gap, and originally meeting when Liam was just 14-years-old on The X Factor, Cheryl and Liam instantly hit it off, posting a number of adorable snaps together.
2016-2018: Liam Payne
After what was the worst kept pregnancy secret of the decade, Cheryl and Liam welcomed a baby boy into the world in March 2017, settling on the name Bear Grey Payne.
2016-2018: Liam Payne
Split rumours started to hit the pair in early 2018, but Cheryl and Liam were quick to shut them down, putting on a very loved-up display at the 2018 BRIT Awards. However, just five months later, the couple released a joint statement admitting they've decided to separate. Despite this, the pair remain good friends and co-parent baby Bear.
And while Cheryl’s never reminisced about her other exes, even after her divorce from Ashley was finalised, she said, “I’ll never stop loving Ashley. He’s a big part of my life. I don’t think he ever wanted to let it go. We had a great relationship. He was my best friend.”
Ashley, 39, has gone on to become a settled family man and has been in a relationship with Italian model Sharon Canu since 2014, and the couple have Jaxon, four, and Grace, one. Last year he implied he was a changed man, saying, “These are the things I focus on now – my kids and my girlfriend. It’s a different me, I’m more of a family man now.”
Insiders reveal there are rumours Ashley is considering proposing, and pals wouldn’t be surprised if the news has rattled Cheryl – who is currently single – and that she could be surprised how much it still affects her.
The source says, “When a mutual pal told Cheryl there’s gossip in the friendship circle that Ashley is thinking of proposing, friends worried that she could be a bit upset by the thought that he could marry again. Her pals believe she’s bound to be surprised at how rubbish it may make her feel. They’re concerned that Cheryl could be shocked that the news of a potential wedding – whether it goes ahead or not – still has the ability to unsettle her.
“While she’s moved on, pals are worried that Cheryl may feel sad that she didn’t have that life with Ashley and that it didn’t work out between them. They fear she feels like she’ll always be haunted by his memory and how things didn’t go as she’d wanted.”
Cheryl has maintained a strong friendship with Liam as they co-parent Bear, regularly praising him publicly, but she’s always wanted the big family and happy relationship.
Last year, the former Girls Aloud star – who’s one of five children herself and has always been open about the fact she wants a big family, once saying she’d like “100 children” – revealed she’s looking into all the ways she could give Bear a sibling, adding, “If time was on my side and I was in my twenties, I’d consider my options, or wait for somebody I felt was right.”
Pals say that hearing how Ashley is having that family life with someone else has hit home for Cheryl – who’s admitted to having counselling to recover from a nervous breakdown following their divorce – that she’s a way off from that.
The source says, “She’s pleased and feels lucky she has such a strong friendship with Liam, and that they’re bringing up Bear together. But she’s craving the family life she’s always wanted, while now he’s reinvented himself and he’s the one who is close to getting married again and already has the perfect family unit.”
WATCH: Kimberly Walsh talks play dates with Cheryl and Bear | This Morning Live
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Worried Cheryl: ‘I’m scared of what Liam Payne will do next’
Earlier this year, Closer revealed how the ten-year anniversary of Cheryl’s split from Ashley stirred up difficult memories for her, coming just months after she was left shaken by reports he was house-hunting close to her new Buckinghamshire mansion – into which she moved following her split from Liam, 26 – but he hasn’t moved yet.
While the Newcastle-born star has since insisted she’d “happily date a Sainsbury’s shelf-stacker”, pals say she’s determined not to rely on a man to find inner happiness and has vowed to ensure she doesn’t let her past heartache define her future.
The source adds, “Cheryl’s a tough cookie and a fighter, and won’t let this set her back for long – especially when she’s come so far and has so much to feel positive and grateful for.”
Read even more celeb stories in this week's Closer magazine - out now.