Britney Spears joyously wed her longtime partner Sam Asghari last June after five years of dating, most of which occurred during her now terminated 13-year conservatorship.
But, just 14 months after tying the knot, Britney, 41, and Sam, 29, have split.
Below is a history of Britney’s relationships going back to her earliest days as a rising performer.
Britney Spears joyously wed her longtime partner Sam Asghari last June after five years of dating, most of which occurred during her now terminated 13-year conservatorship. But, just 14 months after tying the knot, Britney, 41, and Sam, 29, have split; seen in 2019
Donald ‘Reg’ Jones (1995–1997)
Britney got 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 2001, Jones put up two letter than the singer had written him while she was a teen, include one in which she broke up with him.
Justin Timberlake (1998–2002)
Britney’s first serious relationship was with her former Mickey Mouse Club costar Justin Timberlake, who was then part of NSYNC.
Following their 2002 split, the singer 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.
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)
Wade Robson (2002)
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.
Although it was never been confirmed by any of the trio, at the time it was rumoured that Wade was the real reason for the Justin and Britney split.
Yet their relationship was short lived and Britney and Wade had split within the year.
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
Fred Durst (2003)
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.
‘It just became a fiasco of madness,’ Durst told MTV of the alleged breakup. ‘[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.’
Conflicting statements: After the breakup with Robson, Limp Bizkit frontman Fred Durst (pictured in 2003) claimed that he dated Britney, though she denied that they ever had a relationship; seen in 2019
Jared Leto (2003)
Britney was also rumored around this time to have dated Jared Leto, but he never confirmed the alleged romance and she denied that they were eve ran item.
After they were seen together, she said they were just ‘really good friends.’
The dating rumours started after fans theorised that Spears had gone after Leto because he was Cameron Diaz’s ex and Diaz, at the time, was dating Spears’ ex Timberlake.
Rumors: Around 2003, Britney was rumored to be dating Jared Leto (pictured in 2003) after they were seen together, but he never confirmed it and she denied it; seen in March in Austin, TX
Colin Farrell (2003)
There was clearly something going on between Britney and actor Colin Farrell in 2003, when they were seen kissing at the premiere of his film The Recruit, where they also walked the red carpet.
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.’
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
Columbus Short (2003)
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, though he didn’t specify who said it and they both denied using the word.
Columbus claimed to have only had sex with her once, and he claimed he was fired after he failed to reciprocate her affections.
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
Jason Alexander (2004)
Britney’s first (brief) marriage was to Jason Alexander, who had been her friend since childhood. He ended up crashing her wedding to Sam on the morning of the nuptials.
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.
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.’
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
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.
Jason is now in the custody of the Ventura Sheriff’s Department having been charged with trespassing, vandalism and two batteries after a couple of altercations with Britney’s security guards.
Minutes before he was apprehended, Alexander managed to broadcast himself on Instagram as he ran through hillside trails, as he approached the rear of Spears’ home.
Chaos: While the celebrity guests seemed in good spirits, the wedding got off to fraught start when Britney’s ex-husband Jason Alexander was arrested for trespassing
The 40-year-old was easily able to scale a fence, descend a rocky hillside and slip inside the wedding venue, all-the-while telling security exactly who he was, and why he was there – just hours before the fairytale ceremony got underway.
Alexander’s arrest is the third arrest in 13 months. Police sources revealed he also has a felony warrant for larceny in another county.
He was last in police custody for driving under the influence in January 2021 and breaking security protocols at an airport in August. Alexander was also arrested previously for violating an order of protection and stalking an unidentified woman in December 2021.
On Thursday night, Spears’ attorney revealed he was ‘absolutely livid’ after Alexander crashed the pop star’s wedding venue and demanded he be locked up.
Kevin Federline (2004–2007)
The songstress’ next relationship also resulted in a marriage.
Britney and Kevin Federline, a backup dancer, would go on to share her two sons: Sean, 16, and Jayden, 15.
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.
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)
J. R. Rotem (2007)
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
Isaac Cohen (2007)
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.
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.’
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
Howie Day (2007)
Britney reportedly met the singer–songwriter Howie Day while both were at the Promises rehab center in Malibu.
Life & Style reported at the time that Britney’s mother Lynne was concerned about the relationship, which didn’t last long.
Spears’ second husband K Fed also didn’t approve of the relationship, branding Day ‘trash,’ and adding that Britney had to ‘head to the dump’ to meet Day while in rehab.
Rehab relationship: Britney reportedly met the singer–songwriter Howie Day (pictured in 2005) while both were at the Promises rehab center in Malibu; seen in 2016 in LA
Adnan Ghalib (2007–2008)
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, though 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.
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
Jason Trawick (2009–2013)
One of Spears’ longest relationship was with her former agent, Jason Trawick.
In 2021, rumors spread claiming the two had secretly married and then divorce in 2012 after records showing her conservatorship put a lawyer on retainer shortly before their 2013 breakup.
However, Trawick denied that they were ever married, and no marriage license — or divorce — was ever filed.
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)
David Lucado (2013–2014)
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.’
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.’
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)
Charlie Ebsersol (2014–2015)
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… 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.
Exes: Britney continued to date within the entertainment industry, though her new boyfriend Charlie Ebersol was a film and television producer (pictured in 2015)
Sam Asghari (2016–2023)
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.
They married on June 9 2022 at her Thousand Oaks home in a ceremony attended by Madonna.
The pair’s split was revealed in August 2023.
Love of her life: Britney had been with Sam 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