Britney Spears’ tumultuous relationship history: As the star splits from husband Sam Asghari – a look back at her 55-hour Vegas marriage, a bitter divorce from Kevin Federline and Justin Timberlake heartbreak
Britney Spears and her husband Sam Asghari have split over reported rumours the popstar was unfaithful to her husband-of-14 months.
The news rocked the internet as it broke online that they were going their separate ways – another devastating blow to the singer’s already very-turbulent love life.
Sources told TMZ that the Hit Me Baby One More Time songstress, 41, and the actor, 29, were ending their marriage after they got into a ‘nuclear argument’ over his belief that she had cheated on him.
When Britney and Sam tied the knot at her California mansion last June – it seemed as though she had finally found her happy ending after a rollercoaster ride quest to find love – which was filled with failed romances, ugly breakups, and bitter divorces.
Arguably her most famous relationship was with fellow musician Justin Timberlake – who quickly became Hollywood’s ‘it’ couple when they started dating back in 1998.
Toxic! Britney Spears and her husband Sam Asghari have split over reported rumours the popstar was unfaithful to her husband-of-14 months
But when their relationship came crashing down four years later, it ended in an explosive and highly-publicized feud that saw Justin publicly bash his ex on numerous occasions.
Britney wed dancer Kevin Federline in 2004, but as was with Justin, the demise of their relationship played out in the public eye as millions watched on.
The two became embroiled in a nasty custody battle following their divorce in 2007, which ultimately resulted in Britney suffering from a mental breakdown that saw her locking herself in a bathroom with their two sons when it was time for her to return them to their father.
After years of heartbreak, many were hopeful that the star had finally found her soulmate when she walked down the aisle with Sam just over one year ago, but now that too has come to an end.
As news of her and Sam’s breakup continue to make its way around the web, take a look back at the popstar’s extremely messy dating history.
1995 to 1997: Britney was just 14 years old when she hooked up with her first official boyfriend Donald ‘Reg’ Jones
Britney paired up with her first official boyfriend, Reg Jones, when she was only 14 and he was 17.
In Lynne Spears’ 2008 memoir Through The Storm, Britney’s mother claimed that it was actually Jones whom her daughter lost her virginity to, not her future boyfriend Justin Timberlake.
In 2021, Jones put two letters up for sale that the singer had written him while she was a teen, including one in which she broke up with him, which had an estimated price tag of $4,000 to $6,000 each.
Speaking to the New York Post at the time of the sale, he candidly revealed: ‘She was the love of my life.
‘I don’t go around wishing we were back together… I wish her the best in all that she does.’
He also said that the former couple had not spoken in 15 to 20 years, adding: ‘I would like to talk to her, whether it’s this year or 20 years from now, in order to close that chapter of our lives.
‘It felt like we were so in love, so in love, and it was an abrupt ending. Not because of me, not because of her, but because of the industry.’
1998 to 2002: She later paired off with fellow singer Justin Timberlake who used their split to promote his ‘heartbreak’ music
Britney’s first serious relationship was with her former Mickey Mouse Club costar Justin Timberlake, who was then part of NSYNC.
In a 2001 interview, she told The Guardian: ‘I’m not ashamed at all to say that I love him from the bottom of my heart. As far as love is concerned, with him, too much is not enough. He’s everything.
‘We’ve gone through so much together and we’ve known each other since we were 12 years old. We know each other inside and out.’
Years after their split, Timberlake told KLTV: ‘I was infatuated with her from the moment I saw her.’
Big love: Britney’s first serious relationship was with her former Mickey Mouse Club costar Justin Timberlake. Last year, he wrote a public apology after fans were outraged at how the breakup was portrayed in multiple documentaries (pictured 2001)
But the fairytale wasn’t meant to be – and, in 2002, the duo told the press separately that they were no longer together.
In the aftermath, Timberlake publicly blamed Spears for their break up and used his ‘heartbreak’ to promote his music.
A lookalike actress was also used to represent Spears in his video for Cry Me A River, which fans took to be a breakup song about their relationship.
Timberlake later wrote in an open apology that he was ‘deeply sorry’ and would ‘take accountability’ admitting that he had ‘failed’ her, after their relationship came under fresh scrutiny following the release of documentaries looking into Spears’ conservatorship.
2002: Britney’s relationship with choreographer Wade Robson was short lived
The Toxic singer reportedly moved on in the wake of her split from Timberlake with choreographer Wade Robson, who worked for both her and Justin’s group NSYNC.
In 2001, Wade choreographed her iconic Oops… I Did It Again and I’m A Slave 4 U music videos as well as her Live from Las Vegas concert special.
Although it was never been confirmed by any of the trio, at the time it was rumored that he was the real reason for the Justin and Britney split.
Dancer: The Toxic singer reportedly moved on in the wake of her split from Timberlake with choreographer Wade Robson, who worked for both her and Justin’s group NSYNC. Their relationship ended within the year; seen in 2001
Britney said of the choreographer on Good Morning America in 2000: ‘He’s just like a child prodigy, seriously… He’s a genius. He’s amazing.’
Yet their relationship was short lived and Britney and Wade had split within the year.
Wade largely stayed out of the limelight in the aftermath but resurfaced in the 2019 Leaving Neverland documentary in which he detailed the alleged abuse he suffered as a child by Michael Jackson.
2003: Fred Durst claimed he dated Britney – but she has denied any kind of relationship
After the breakup with Robson, Limp Bizkit frontman Fred Durst claimed that he dated Britney, though she denied that they ever had a relationship.
The couple spent time together when working on songs for Britney’s new album but she was quick to shut down the rumors.
Conflicting statements: After the breakup with Robson, Limp Bizkit frontman Fred Durst claimed that he dated Britney, though she denied that they ever had a relationship; seen in 2019
The singer told Carson Daly: ‘The thing is we worked together for like three days and he’s a really cool guy but there’s no relationship.’
Addressing the back and forth, Durst told MTV: ‘It just became a fiasco of madness.
‘[But] I always stay true to my heart and true to everything I did and my intentions, and I am in no way a liar.’
2003: Neither Britney nor Jared Leto confirmed their alleged romance despite being engulfed in rumors
Britney was also rumored around this time to have dated Thirty Seconds to Mars frontman Jared Leto.
He never confirmed the alleged romance and she denied also that they were ever an item despite being engulfed in rumors.
Rumors: Around 2003, Britney was rumored to be dating Jared Leto after they were seen together, but he never confirmed it and she denied it; seen in March in Austin, TX
After the pair were spotted out and about together, she eventually came out and said they were just ‘really good friends.’
The dating rumors started after fans theorized that Spears had gone after Leto because he was Cameron Diaz’s ex and Diaz, at the time, was dating Spears’ ex Timberlake.
2003: Sparks clearly flew between the singer and Colin Farrell but it turned out to be just a fling
There was clearly something going on between Britney and actor Colin Farrell in 2003.
Sparks flew when they were seen kissing at the premiere of his film The Recruit, where they also walked the red carpet.
Nothing to see here: Colin Farrell and Britney were seen kissing in 2003 at the premiere of his film The Recruit, but he denied there was anything serious going on between them
However, he shrugged the affectionate display off and said he was ‘just a 26-year-old guy who’s single and having a good time.’
While their fling may only have lasted a week, Farrell memorialized their relationship by sending Spears a shirt that read: ‘I slept with Colin Farrell and all I got was this lousy T-shirt.’
2003: Britney and her backup dancer Columbus Short hooked up before he made claims she used a racist slur
Britney dated within her own organization when she hooked up with her backup dance Columbus Short in 2003.
Short, who subsequently starred on Scandal, later claimed that he overheard Spears’ parents Lynne and Jamie Spears refer to him by the N-word when she was on speaker phone with them
Offensive language: Britney began dating her backup dance Columbus Short in 2003. He claimed he overheard one of her parents refer to him by the N-word, though both denied the incident
The dancer did not specify who made the remark but both vehemently denied using the word.
Columbus said to have only had sex with her once, and he claimed he was fired after he failed to reciprocate her affections.
2004: Britney first tied the knot to childhood friend Jason Alexander
Britney’s first (brief) marriage was to Jason Alexander, who had been her friend since childhood.
The couple tied the knot on a whim in the early morning hours on January 3, 2004 during a ceremony at the Little White Wedding Chapel in Las Vegas, Nevada.
They were both 22 years old at the time.
Quick turnaround: Britney’s first (brief) marriage was to Jason Alexander, who had been her friend since childhood. They eloped in Las Vegas at the Little White Wedding Chapel, but they famously got the union annulled after just 55 hours
But their marriage was annulled 55 hours later, which Alexander later claimed was forced by Britney’s mother, Lynne, and Britney’s management.
Following the annulment, Spears said in an interview: ‘It was me being silly, being rebellious.’
Yet 18 years after their union it seems Alexander hasn’t lost his feelings for Spears, as just hours before she was was due to marry her long-term partner Sam Asghari, 28, at her home Alexander broke onto the premises to crash the wedding.
2004 to 2007: Britney ended up welcoming two sons with dancer Kevin Federline
The songstress’ next relationship also resulted in a marriage.
Britney met former backup dancer Kevin Federline at a club in Hollywood called Joseph’s in the summer of 2004.
He told People in 2008, after their divorce: ‘Our eyes met and that was it. We just hit it off right away. I learned real fast how much of a whirlwind the press and everything was.’
The pair married at a private home in Studio City, California, just three months later and went on to welcome two sons: Sean, 16, and Jayden, 15.
Marriage no. 2: Spears was married to her second husband Kevin Federline from 2004–2007. In January 2008, she was put on a psychiatric hold after refusing to return their sons Sean and Jayden to him (pictured in 2005)
The couple divorced in 2007, and it was her struggles with custody that factored into the creation of her conservatorship.
In January 2008, she locked herself in a bathroom with the children when it was time to return them to their father.
The police were subsequently called, and Spears was put on a 5150 psychiatric hold.
2007: J. R. Rotem gave graphic details about his physical relationship with Britney before claiming it was a ‘stupid phase’
Spears hit the dating scene quickly following her divorce when she got together with the music producer J. R. Rotem, who produced her song Everybody.
Following their fling, Rotem shocked with a graphic kiss and tell interview, crudely announcing ‘I f**ked Britney wheelbarrow style – it was tractor style.’
Reflecting on their union, Rotem later said: ‘It was kind of a stupid phase I was going through, where I wouldn’t say that I was being a bad person but I would say that I was being not very genuine to who I am and what it is that I’m supposed to do.’
Passing through: Britney hit the dating scene quickly following her divorce when she got together with the music producer J. R. Rotem, though the relationship appears to have been short-lived
In the aftermath, he told Complex magazine: ‘Now it’s kind of rocky between us. We’re working together still, but I’m not sure if I want to be tied down, period.’
Rotem then boasted of his other celebrity pairings – but did not state if they were personal or professional.
‘Britney, Mya, Bai Ling, Hayden Panettiere, Meagan Good — it’s a pretty big list, and it’s growing. Britney got me the furthest. She had something special,’ he said.
2007: Britney began dating model Isaac Cohen before the pair went through an ‘amicable’ break up
In the same year as her fling with Rotem, Spears began dating male model Isaac Cohen.
At the time, her fans noted that Cohen noted only looked like her ex-husband Kevin, but he even favored similar clothing to the dancer.
Lookalike: In the same year as her fling with Rotem, Spears began dating male model Isaac Cohen. At the time, her fans noted that Cohen noted only looked like her ex-husband K Fed, but he even favored similar clothing to the dancer
Their breakup was described as ‘amicable,’ and Cohen later said of their relationship: ‘By the time I met Britney she was burnt out.
‘She knew she had been drinking and partying as a way to try to banish the bad stuff from her life.
‘Far from the trashy drunk, I saw a very shy, sweet girl who was just desperately sad about what had happened with her marriage.’
2007: Britney’s mom was concerned about the singer’s relationship with Howie Day – but it did not last long
Britney reportedly met the singer–songwriter Howie Day while both were at the Promises rehab center in Malibu in 2007.
Life & Style reported at the time that Britney’s mother Lynne was concerned about the relationship after learning about Day’s previous arrest.
Rehab relationship: Britney reportedly met the singer–songwriter Howie Day while both were at the Promises rehab center in Malibu; seen in 2016 in LA
But the romance did not last long.
Spears’ second husband K Fed also didn’t approve of the relationship, branding Day ‘trash.’
He also added that Britney had to ‘head to the dump’ to meet Day while in rehab.
2007 to 2008: The star shocked fans when she began dating the paparazzo Adnan Ghalib
The pop star shocked her fans and family when she began dating the paparazzo Adnan Ghalib in 2007, despite the fact that he had long been on her tail hunting for the perfect photo.
Ghalib claimed in 2008 that he had a sex tape featuring Spears in an apparent bid to shop it around.
Shocker: The pop star surprised fans and family when she began dating the paparazzo Adnan Ghalib in 2007, despite the fact that he had long been on her tail hunting for the perfect photo
But he later claimed his statements were fabricated, according to The Daily Beast.
Britney’s father Jamie successful won a restraining order to keep Ghalib away from his daughter by claiming that the photographer alerted paparazzi to Britney’s whereabouts and then got a fee from them.
2009 to 2013: Britney enjoyed a lengthy relationship with former agent Jason Trawick but the pair never married
One of Spears’ longest relationship was with her former agent, Jason Trawick.
In 2021, rumors spread claiming the two had secretly married and then divorced in 2012 after records showing her conservatorship put a lawyer on retainer shortly before their 2013 breakup.
Steady: One of Spears’ longest relationship was with her former agent, Jason Trawick. Last year, rumors emerged that they had gotten married and divorce in 2012, but a marriage license was never filed (pictured in 2012)
However, Trawick denied that they were ever married, and no marriage license — or divorce — was ever filed.
It is thought that their relationship simply fizzled out.
2013 to 2014: Britney dumped David Lucado after she reportedly caught him cheating
Britney and David Lucado began dating shortly after her split from Trawick, though the relationship only lasted about a year.
According to TMZ, Britney dumped Lucado after she discovered a video showing Lucado ‘making out with a woman and dancing with her.’
That was fast: Britney and David Lucado began dating shortly after her split from Trawick, though the relationship only lasted about a year (pictured in 2014)
Lucado didn’t take the split well, with a representative telling TMZ: ‘David is very, very in love with Britney.
‘This is unfortunate and he hopes that it all works out.’
But following their separation it seemed Spears was ready for to return to dating, tweeting at the time: ‘Ahhhh the single life!’
2014 to 2015: The performer fell for the calming presence of producer Charlie Ebsersol – before her father intervened
Spears continued to date within the entertainment industry, though her new boyfriend Charlie Ebersol was a film and television producer.
Speaking about their romance Spears said at the time: ‘I thought he was really adorable and she said he was good to people, so I went for it…
Exes: Britney continued to date within the entertainment industry, though her new boyfriend Charlie Ebersol was a film and television producer (pictured in 2015)
‘There was something about him that made me feel really peaceful and at ease.’
Sources claimed to Hollywood Life after their breakup that the two separated after Britney’s father Jamie suggested he wasn’t a good match for her.
A source told Us Weekly at the time that he was in the relationship for ‘the wrong reasons.’
2016 to 2023: Britney has been with Sam Asghari for years but the pair split after being engulfed in break-up speculation
Sam Asghari, an aspiring actor, has been by the pop star’s side since 2016, making their relationship her longest to date.
She met Sam in 2016 when he appeared in her Slumber Party music video, and the two quickly hit it off after that.
They went Instagram official in January 2017, and Sam was by her side amid the battle to end her long-running conservatorship.
Spears announced their engagement on September 12, 2021, and she followed the good news up by having her conservatorship terminated in November of that year.
In April 2022, the couple announced they were expecting their first child together, but Britney revealed just a month later that she had suffered a miscarriage.
‘Perhaps we should have waited to announce until we were further along however we were overly excited to share the good news,’ she wrote on Instagram.
Love of her life: Britney has been with her love Sam Asghari since 2016, when he appeared in her Slumber Party video. They got engaged in September 2021 and announced her pregnancy in April 2022, before she suffered a miscarriage in May
In March 2023, speculation started to swirl that they had gone their separate ways after they were seen without their wedding rings.
However, at the time, an insider close to the pair insisted to DailyMail.com that they were still going strong.
‘All is good,’ the source said. ‘Sam is working on a project and she is on a vacation with [her friend and manager] Cade [Hudson].’
But now, TMZ has reported that they’re over after they got into a ‘huge fight’ surrounding allegations that she had been unfaithful. It is unconfirmed whether Britney cheated on Sam.
A source told the publication that Sam has moved out of their house and is now living in a place of his own.
They added: ‘It’s only a matter of time before Sam files for divorce.’
DailyMail.com has contacted representatives for Spears for comment.
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