Britney Spears happily wed longtime partner Sam Asghari last June after dating for five years, most of them during their now-completed 13-year conservatory years.
But just 14 months after tying the knot, Britney, 41, and Sam, 29, have split.
Below is a history of Britney’s relationships, stretching back to her early days as an aspiring artist.
Britney Spears happily wed longtime partner Sam Asghari last June after dating for five years, most of them during their now-completed 13-year conservatory years. 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 to whom her daughter lost her virginity, and not her boyfriend-to-be Justin Timberlake.
In 2001, Jones released two letters the singer wrote to him as a teenager, including one in which she broke up with him.
Justin Timberlake (1998-2002)
Britney’s first serious relationship was with her former Mickey Mouse Club co-star Justin Timberlake, who was then part of NSYNC.
Following their split in 2002, the singer publicly blamed Spears for the breakup and used his “heartbreak” to promote his music. A double was also used to portray Spears in his video for “Cry Me A River,” which fans took to be a breakup song about their relationship.
Timberlake later wrote in a candid apology that he was “deeply sorry” and would “take responsibility” by admitting he had “abandoned her” after their relationship following the release of Spears’ conservatory documentaries was put to the test again.
Great love: Britney’s first serious relationship was with her former Mickey Mouse Club co-star Justin Timberlake. He wrote a public apology last year after fans were outraged at how the split was portrayed in several documentaries (pictured in 2001).
Wade Robson (2002)
Following her split from Timberlake, the Toxic singer reportedly moved on with choreographer Wade Robson, who worked for both her and Justin’s group NSYNC.
Although this hasn’t been confirmed by any of the trio, there were rumors at the time that Wade was the real reason Justin and Britney split.
However, their relationship was short-lived and Britney and Wade broke up within a year.
Dancer: Following her split from Timberlake, the Toxic singer reportedly moved on 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 Robson split, Limp Bizkit frontman Fred Durst claimed he dated Britney, though she denied they ever had a relationship.
The pair spent time together while working on songs for Britney’s new album.
“It just became a fiasco of insanity,” Durst told MTV of the alleged breakup. ‘[But] “I always stay true to my heart and true to everything I’ve done and my intentions, and I’m in no way a liar.”
Conflicting statements: After splitting with Robson, Limp Bizkit frontman Fred Durst (pictured in 2003) claimed he dated Britney, although she denied they ever had a relationship; seen in 2019
Jared Leto (2003)
It was also rumored at the time that Britney was dating Jared Leto, but he never confirmed the alleged romance and she denied they ever dated.
After they were spotted together, she said they’re just “really good friends.”
The dating rumors began after fans theorized that Spears had been pursuing Leto because he was Cameron Diaz’ ex and Diaz was dating Spears’ ex Timberlake at the time.
Rumours: Around 2003 Britney was rumored to be dating Jared Leto (pictured in 2003) after they were spotted together but he never confirmed it and she denied it; seen in Austin, TX in March
Colin Farrell (2003)
Something was clearly going on between Britney and actor Colin Farrell in 2003, when they were spotted kissing at the premiere of his movie The Recruit, where they also walked the red carpet.
However, he shrugged off the affectionate display, saying he’s “just a 26-year-old guy who’s single and having a good time.”
While their affair may have only lasted a week, Farrell commemorated their relationship by sending Spears a t-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 spotted kissing at the premiere of his film The Recruit in 2003, but he denied there was anything serious going on between them
Columbus Short (2003)
Britney was within her own organization when she joined her backup dance group Columbus Short in 2003.
Short, who later starred in “Scandal,” later claimed he overheard Spears’ parents Lynne and Jamie Spears using the N-word when she spoke to them on the speakerphone. However, he did not specify who said it, and both denied using the word.
Columbus claimed to have had sex with her only once and claimed he was fired for not reciprocating her affections.
Offensive language: Britney began dating her backup dance partner Columbus Short in 2003. He claimed he heard one of her parents address him with the N-word, although both denied the incident
Jason Alexander (2004)
Britney’s first (brief) marriage was to Jason Alexander, who had been her boyfriend since childhood. Finally, on the morning of the wedding, he interfered with her marriage to Sam.
The couple tied the knot on a whim in the early hours of 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 coerced by Britney’s mother Lynne and Britney’s management. After the annulment, Spears said in an interview, “I was silly and rebellious.”
Quick turnaround: Britney’s first (brief) marriage was to Jason Alexander, who had been her boyfriend since childhood. They fled to the Little White Wedding Chapel in Las Vegas, but the marriage is known to have been annulled after 55 hours
But 18 years after their wedding, Alexander doesn’t seem to have lost his feelings for Spears, because just hours before she was due to wed her longtime partner Sam Asghari, 28, at her home, Alexander broke into the grounds and called off the wedding.
Britney’s first husband Jason Alexander has been sentenced to jail after he dramatically livestreamed how he crashed their wedding at their Thousand Oaks mansion.
Jason is now in the care of the Ventura Sheriff’s Department after being accused of trespassing, vandalism and two batteries following some altercations with Britney’s security guards.
Minutes before he was arrested, Alexander managed to show on Instagram running down mountain trails and approaching the back of Spears’ home.
Chaos: While the celebrity guests appeared to be in good spirits, the wedding got off to a tumultuous start when Britney’s ex-husband Jason Alexander was arrested for trespassing
The 40-year-old easily scaled a fence, descended a rocky cliff and slipped into the wedding venue while telling security guards exactly who he was and why he was there – just hours before the fairytale ceremony began in progress.
Alexander’s arrest is the third arrest in 13 months. According to police sources, he also has an arrest warrant for theft in another county.
He was most recently in police custody in January 2021 for driving under the influence and violating safety protocols at an airport in August. Alexander was previously arrested for violating a protective order and stalking an unidentified woman in December 2021.
On Thursday night, Spears’ attorney revealed he was “absolutely furious” after Alexander crashed the pop star’s wedding venue and demanded that he be locked up.
Kevin Federline (2004-2007)
The singer’s next relationship also ended in marriage.
Britney and Kevin Federline, a backup dancer, later shared their two sons: Sean, 16, and Jayden, 15.
The couple divorced in 2007 and it was their custody issues that helped establish their conservatory office.
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 then called and Spears was placed in psychiatric custody.
Marriage #2: Spears was married to her second husband Kevin Federline from 2004 to 2007. In January 2008, she was committed to a psychiatric ward after refusing to give him back her sons Sean and Jayden (pictured in 2005).
JR Rotem (2007)
Spears quickly burst onto the dating scene following her divorce when she met music producer JR Rotem, who produced her song Everybody.
After their affair, Rotem shocked with a graphic kiss-and-tell interview, rudely proclaiming, “I fucked Britney wheelbarrow style — it was tractor style.”
Reflecting on their connection, Rotem later said, “It was kind of a stupid phase I went through where I wouldn’t say I’m a bad person, but I would say I’m not very sincere about that.” am what I am.’ and what I should do.’
Passing through: Britney quickly burst onto the dating scene following her divorce when she hooked up with music producer JR Rotem, though the relationship appeared to be short-lived
Isaac Cohen (2007)
The same year that she began dating Rotem, Spears began dating male model Isaac Cohen.
Back then, her fans noticed that Cohen only resembled her ex-husband Kevin, but even preferred him to wear clothes similar to the dancer’s.
Their split was described as “amicable,” and Cohen later said of their relationship, “When I met Britney, she was burned out.” She knew that by drinking and partying, she was trying to keep the bad things out of her life.
“Apart from the cheesy drunk, I saw a very shy, sweet girl who was just desperately sad about what had happened to her marriage.”
Lookalike: The same year that she began dating Rotem, Spears began dating male model Isaac Cohen. Back then, her fans noticed that Cohen only resembled her ex-husband K Fed, but he even preferred clothes similar to the dancer
Howie Day (2007)
Britney reportedly met singer-songwriter Howie Day while they were both at Promises rehab center in Malibu.
Life & Style reported at the time that Britney’s mother, Lynne, was worried about the relationship, which didn’t last long.
Spears’ second husband K Fed also disagreed with the relationship, branding Day “garbage” and adding that Britney had to “go to the dump” to meet Day during rehab.
Rehab relationship: Britney reportedly met singer-songwriter Howie Day (pictured in 2005) while they were both at Promises rehab center in Malibu; seen in LA in 2016
Adnan Ghalib (2007–2008)
The pop star shocked her fans and family when she started dating paparazzi Adnan Ghalib in 2007, even though he had long been on her tail in search of the perfect photo.
Ghalib claimed in 2008 that he had a sex tape with Spears, apparently with intent to mess with it. However, according to The Daily Beast, he later claimed his statements were fabricated.
Britney’s father Jamie successfully obtained an injunction to keep Ghalib away from his daughter, alleging that the photographer alerted paparazzi to Britney’s whereabouts and then received a fee from them.
Shocking: The pop star surprised fans and family when she began dating paparazzi Adnan Ghalib in 2007, despite him having long been on her tail in search of the perfect photo
Jason Trawick (2009-2013)
One of Spears’ longest relationships was with her former agent Jason Trawick.
In 2021, rumors spread that the two secretly married and then divorced in 2012 after records showed their conservatory work had hired a lawyer shortly before their split in 2013.
However, Trawick denied ever getting married, and no marriage license — or divorce — was ever filed.
Steady: One of Spears’ longest relationships was with her former agent Jason Trawick. Rumors circulated last year that they got married and divorced in 2012, but a marriage certificate was never submitted (pictured in 2012).
David Lucado (2013-2014)
Britney and David Lucado began dating shortly after her split from Trawick, although the relationship only lasted about a year.
According to TMZ, Britney dumped Lucado after spotting a video of Lucado “making out and dancing with a woman.”
Lucado didn’t take the breakup well, with a rep telling TMZ, “David is very, very much in love with Britney.” It’s unfortunate and he’s hoping things work out.”
It happened quickly: Britney and David Lucado started dating shortly after her split from Trawick, although the relationship only lasted about a year (pictured in 2014)
Charlie Ebsersol (2014-2015)
Spears continued to be involved in the entertainment industry even though her new boyfriend, Charlie Ebersol, was a film and television producer.
Speaking of their romance at the time, Spears said, “I found him really adorable and she said he was good with people, so I gave it a try … There was something about him that made me feel really peaceful and relaxed.”
Sources claimed to Hollywood Life after their split that the two broke up after Britney’s father Jamie suggested he wouldn’t be a good match.
Ex-partner: Britney continued to be involved in the entertainment industry, although 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 at the pop star’s side since 2016, making their relationship their longest to date.
She met Sam in 2016 when he appeared in her music video “Slumber Party,” and the two hit it off quickly afterward.
In January 2017, they officially went on Instagram and Sam was by their side as they battled to end their longtime conservatory tenure.
Spears announced their engagement on September 12, 2021, and she followed the good news by retiring from conservatory work in November of the same year.
In April 2022, the couple announced they were expecting their first child together, but Britney announced just a month later that she had suffered a miscarriage.
“Maybe we should have waited until we were further along to announce it, but we were overly excited to share the good news,” she wrote on Instagram.
They wed on June 9, 2022 at their home in Thousand Oaks in a ceremony attended by Madonna.
The couple’s split was announced in August 2023.
Love of her life: Britney had been dating Sam since 2016 when he appeared in her slumber party video. They got engaged in September 2021 and announced their pregnancy in April 2022 before suffering a miscarriage in May