Britney Spears joyfully married her longtime partner Sam Asghari last June after five years of relationship, most of which took place during their now-completed 13-year conservatorship.
But just 10 months after they tied the knot, rumors are swirling that there could be trouble in paradise as both Britney, 41, and Sam, 28, have shed their wedding rings in recent days.
Below is a history of Britney’s relationships, dating back to her earliest days as an aspiring artist.
Britney Spears joyfully married her longtime partner Sam Asghari last June after five years of relationship, most of which took place during their now-completed 13-year conservatorship. But just 10 months after they tied the knot, rumors are circulating there could be trouble in paradise as both Britney, 41, and Sam, 28, have shed their wedding rings in recent days; 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 left behind two letters the singer had written 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 their split and used his “heartbreak” to promote his music. A double 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 a candid apology that he was “deeply sorry” and would “hold it accountable” by admitting that he “abandoned her” after their relationship after the release of documentaries dealing with Spears’ custody had come under renewed scrutiny.
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.
Though it was never confirmed by either trio, it was rumored 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: The Toxic singer reportedly moved on after 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 Robson split, Limp Bizkit frontman Fred Durst claimed he dated Britney, though she denied they ever had a relationship.
The couple 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 will always stay true to my heart and everything I have done and my intentions and I am in no way a liar.’
Conflicting claims: After Robson split, 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)
Britney was also reported to be dating Jared Leto around this time, but he never confirmed the alleged romance and she denied they ever dated.
After they were spotted together, she said they were just “really good friends.”
The dating rumors began after fans theorized that Spears had been stalking 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 film The Recruit, where they also walked the red carpet.
However, he shrugged and said he was “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 with her own organization when she teamed up with her backup dance Columbus Short in 2003.
Short, who later starred in Scandal, later claimed he overheard Spears’ parents Lynne and Jamie Spears calling him the N-word when she spoke to them on the speakerphone, although he did not say who said it. and both denied with the word.
Columbus claimed to only have had sex with her once, and he claimed he was fired after failing to return her affections.
Offensive language: Britney started dating her back-up dance, Columbus Short, in 2003. He claimed he overheard one of her parents using the N-word to refer to him, although both denied the incident
Jason Alexander (2004)
Britney’s first (brief) marriage was to Jason Alexander, who had been her childhood friend. On the morning of the wedding, he crashed her marriage to Sam.
The couple married on a whim in the early hours of the morning 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 coerced by Britney’s mother Lynne and Britney’s management. After the annulment, Spears said in an interview, “I was goofy, rebellious.”
Quick turnaround: Britney’s first (brief) marriage was to Jason Alexander, who had been her childhood friend. They eloped at the Little White Wedding Chapel in Las Vegas, but the marriage was known to have been annulled after just 55 hours
But 18 years after their reunion, Alexander doesn’t seem to have lost his feelings for Spears, as just hours before she was due to wed her longtime partner Sam Asghari, 28, Alexander broke into the premises of their home to crash the wedding bring to .
Britney’s first husband Jason Alexander has been jailed after dramatically live-streaming himself crashing their wedding at their Thousand Oaks mansion.
Jason is now in the custody of the Ventura Sheriff’s Department after being charged with trespassing, vandalism and two counts of battery following some altercations with Britney’s security guards.
Minutes before he was arrested, Alexander managed to Instagram himself as he ran through the hilltop paths as he approached 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 was able to easily scale a fence, descend a rocky slope and slip into the wedding site, all the while telling security exactly who he was and why he was there – just hours before the fairytale ceremony took place traveling.
Alexander’s arrest is the third arrest in 13 months. Police sources said he also has a warrant out for his arrest in another county for theft.
He was last in police custody in January 2021 for driving under the influence and violating safety protocols at an airport in August. Alexander had also previously been arrested for violating a protection 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 resulted in a marriage.
Britney and Kevin Federline, a backup dancer, would share their two sons: Sean, 16, and Jayden, 15.
The couple divorced in 2007, and it was their custody battles that helped create their conservatory.
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 taken to a 5150 psychiatric facility.
Marriage #2: Spears was married to her second husband Kevin Federline from 2004–2007. In January 2008, she was placed in a psychiatric detention center after refusing to return her sons Sean and Jayden to him (pictured in 2005).
JR Rotem (2007)
Spears quickly got on the dating scene after her divorce when she met music producer JR Rotem, who produced her song Everybody.
Following their affair, Rotem shocked with a graphic kiss and narrated an interview, rudely proclaiming, “I fucked Britney wheelbarrow style — it was tractor style.”
Reflecting on their union, Rotem later said, “It was kind of a silly phase where I wouldn’t say I’m a bad person, but I would say I’m not very honest about who 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 as her affair with Rotem, Spears began dating male model Isaac Cohen.
At the time, her fans noted that Cohen noted that she only looked like her ex-husband Kevin, but he even favored clothing similar to the dancer.
Their split was described as “amicable” and Cohen later said of their relationship: “When I met Britney she was burnt out. She knew she’d been drinking and partying to try and banish the bad from her life.
“A far cry from the trashy drunk, I saw a very shy, sweet girl who was just desperately sad about what had happened to her marriage.”
Lookalike: The same year as her affair with Rotem, Spears began dating male model Isaac Cohen. At the time, her fans noted that Cohen noted that she only looked like her ex-husband K Fed, but he even favored clothing similar to the dancer
Howie Day (2007)
Britney reportedly met singer-songwriter Howie Day while they were both at Promises rehab 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 both were 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, despite him long chasing her for the perfect photo.
Ghalib claimed in 2008 he had a sextape with Spears in an apparent attempt to poke around it, although he later claimed his statements were fabricated, according to The Daily Beast.
Britney’s father Jamie successfully won an injunction to keep Ghalib away from his daughter, claiming the photographer alerted paparazzi to Britney’s whereabouts and then received a fee from them.
Shocker: The pop star surprised fans and family when she started dating paparazzi Adnan Ghalib in 2007, even though he had long been on her hunt for the perfect photo
Jason Trawick (2009-2013)
One of Spears’ longest relationships was with her former agent, Jason Trawick.
In 2021, rumors spread claiming the pair secretly married and then divorced in 2012, after records showing their conservatorship put a lawyer on hold shortly before their split in 2013.
However, Trawick denied they were ever married, and no marriage certificate — or divorce — was ever filed.
Steady: One of Spears’ longest relationships was with her former agent, Jason Trawick. Last year, rumors surfaced that they married and divorced in 2012, but a marriage certificate was never filed (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, and a rep told TMZ, “David is very, very much in love with Britney. That’s unfortunate and he hopes everything will work out.”
It was quick: Britney and David Lucado began 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 thought he was really adorable and she said he was good with people, so I went for it … There was something about him that made me feel really peaceful and relaxed.”
Sources claimed to Hollywood Life after their split that the two split after Britney’s father Jamie suggested he wasn’t a good match.
Exes: Britney has continued to date in the entertainment industry despite her new boyfriend Charlie Ebersol being a film and television producer (pictured in 2015)
Sam Asghari (since 2016)
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 thereafter.
They officially became Instagram in January 2017 and Sam has been by their side in the fight to bring their longtime conservatory to an end.
Spears announced their engagement on September 12, 2021, and she followed the good news by finishing her conservatory in November of that 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’re further along to announce, but we were overly excited to share the good news,” she wrote on Instagram.
Love of her life: Britney has been dating her love 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