Britney Spears is set to tie the knot with her longtime partner Sam Asghari, 28, on June 9, 2022.
The 40-year-old songstress and her boyfriend have been going strong since linking up in 2016, but their love follows of string of short-lived romances for the pop superstar.
Below is a history of Britney’s relationships going back to her earliest days as a rising performer.
Wedding bells: Britney Spears, 40, is set to tie the knot with her longtime partner Sam Asghari, 28, on June 9, 2022. Below is a history of Britney’s relationships going back to her earliest days as a rising performer; seen in 2019 in Hollywood
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.
Justin’s relationship with Britney was covered in a negative light in a series of documentaries release in the final days of her conservatorship, and he later wrote in an open apology that he was ‘deeply sorry’ and would ‘take accountability.’
Following their 2002 split, the singer used a lookalike actress to apparently stand in for Britney in his video for Cry Me A River, which fans took to be a breakup song about their relationship.
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; seen in 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. Their relationship ended within the year.
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.
‘It just became a fiasco of madness,’ he 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.’
Jared Leto (2003)
Britney was also rumored around this time to have dated Jared Leto following his split from Cameron Diaz, 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.’
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
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
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
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.’
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 Britney’s 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.
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; seen in 2003
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; seen in 2003 in NYC
Jason Alexander (2004)
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 of married life.
Kevin Federline (2004–2007)
The songstress’ next relationship also resulted in a marriage.
Britney and Kevin, 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; seen in 2005 in Hollywood
J. R. Rotem (2007)
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, she began dating the 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.
Though their breakup was described as ‘amicable,’ Cohen later made unflattering statements about his ex.
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; seen in 2007
Lookalike: In the same year, Britney dated the model Isaac Cohen. Her fans noted his similar appearance and style to Kevin; seen in 2007
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.
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 Britney 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.
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
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; seen in 2008 in LA
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.
David Lucado (2013–2014)
Britney and David Lucado began dating shortly after her split from Trawick, though the relationship only lasted about a year.
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; seen in 2012 in LA
That was fast: Britney and David Lucado began dating shortly after her split from Trawick, though the relationship only lasted about a year; seen in 2014
Charlie Ebsersol (2014–2015)
Britney continued to date within the entertainment industry, though her new boyfriend Charlie Ebersol was a film and television producer.
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.
Sam Asghari (2016–)
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.
Britney 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