Britney Spears’ ‘Toxic’ love life: Meet Sam Asghari, Kevin Federline and more
She’s stronger than yesterday.
Newly-single Britney Spears is back on the market after splitting from her third husband, Sam Asghari, in August 2023.
The “Toxic” hitmaker rose to fame in the late ’90s and has had several high profile relationship throughout her decades-long career.
Step back in time as we dive into Spears’ complete dating history.
Justin Timberlake
Spears’ first high-profile relationship was with her “Mickey Mouse Club” co-star Justin Timberlake.
The it-couple started dating in 1998 and their four-year relationship gave us several iconic moments, including their double denim red carpet looks at the 2001 American Music Awards.
Even their eventual split in 2002 made headlines after the former *NSYNC star released his hit “Cry Me a River.”
The music video for the song, and Timberlake’s behavior after their break up, led to speculation that Spears cheated on him.
While the rumors were never substantiated, Timberlake finally faced backlash following the release of the 2021 documentary “Framing Britney Spears.”
The “Mirrors” singer later issued an apology to his ex, owning up to his “ignorance” surrounding the media treatment she faced following their split.
“I’ve seen the messages, tags, comments, and concerns and I want to respond,” he wrote on Instagram in February 2021.
“I am deeply sorry for the times in my life where my actions contributed to the problem, where I spoke out of turn, or did not speak up for what was right. I understand that I fell short in these moments and in many others and benefited from a system that condones misogyny and racism.”
Wade Robson
Wade Robson directed Spears’ 1999 and 2000 world tours, along with her “Dream Within a Dream” tour in 2001.
The famed choreographer, who also appeared in her “(You Drive Me) Crazy” video, is rumored to have secretly hooked up with the pop star while she was still dating Timberlake.
The couple are believed to have dated for about a year, however, neither has spoken publicly about the relationship.
Robson went on to accuse Michael Jackson of sexually abusing him when he was seven years old in the 2019 documentary “Leaving Neverland.”
Colin Farrell
Spears is believed to have met Colin Farrell when she visited the set of “S.W.A.T.” in early 2003.
Fans were shocked when the odd couple attended the premiere of his film “The Recruit” in February of that year.
Although they were pictured getting cozy in front of the cameras, the Irish actor made it clear they weren’t officially dating.
“She’s just a mate,” he told Entertainment Tonight at the time. “Seriously, we just met a week ago, [we’re] having a laugh.”
Spears, for her part, dished to W Magazine about their time together.
“Yes, I kissed him … He’s the cutest, hottest thing in the world — wooh! … But it was nothing serious,” she confessed.
Columbus Short
Later that year, Spears allegedly hooked up with her backup dancer Columbus Short.
The “Scandal” alum claimed in his 2020 autobiography, “Short Stories,” that a “wild party” in 2003 led to the intimate moment.
“[Britney] sent us a jet, and just like that, we were in New York having a wild party for my 21st birthday,” he alleged.
“We ended up being intimate that one time. I never slept with her again after that, though. This was a dangerous sexual alliance for every reason under sun, and I think that the worst part of it was that I was making the rumors an actual reality.”
Spears has never addressed Short’s claims about their alleged hookup.
Jason Alexander
Spears was infamously married to her first husband, Jason Alexander, for just 55 hours in 2004.
The “Gimme More” singer wed her childhood friend at the Little White Wedding Chapel in Las Vegas after a big night of partying.
However, they annulled their union shortly afterward.
Alexander has continued talking about his ex-wife on social media and startled fans when he livestreamed himself breaking into her home hours before her June 2022 wedding to her third husband, Sam Asghari.
He has since moved on with Rebecca Bell, whom he wed in March 2023.
Kevin Federline
Later that year, she announced her engagement to backup dancer Kevin Federline.
The pair tied the knot in September 2004 and welcomed their sons, Sean Preston and Jayden, in September 2005 and 2006, respectively.
The duo got divorced after three years of marriage and spent several years locked in a contentious custody battle that was further complicated by her controversial conservatorship.
In 2023, Federline relocated to Hawaii with his sons and his new wife, Victoria Prince, after she landed a job on the island.
J.R. Rotem
Spears began dating music producer J.R. Rotem shortly after her divorce from Federline in 2007.
The romance was brief and he later claimed he didn’t want “to be tied down,” per Hollywood.com.
Adnan Ghalib
Spears met Adnan Ghalib in late 2007, shortly after shaving her head and hitting a paparazzo’s car with an umbrella.
Bizarrely, the pair began dating in 2008 after he helped her at a gas station while she was being hounded by fellow photographers.
In the 2021 Netflix documentary “Britney vs Spears,” the British paparazzo recalled their year-long romance.
“It was a very simple, very easy relationship, you know? But between her fans and everybody else, it was like I was the bad guy,” he said.
The couple split in 2008 after the pop star was allegedly shown proof that he planned to pull a pregnancy test-buying stunt for publicity.
Jason Trawick
In 2009, Spears began one of her most stable relationships to date with her former manager, Jason Trawick.
The pair started dating in April of that year and got engaged in December 2011.
However, they never made it down the aisle, announcing in January 2013 that they had broken up and mutually called off their engagement.
During their relationship, Trawick briefly had a role as a co-conservator of Britney, alongside her father, Jamie Spears, and attorney Andrew Wallet.
David Lucado
Two months after she split from her ex-fiancé, Britney started dating lawyer David Lucado.
The relationship, which began in March 2013, lasted just over one year, until the “Stronger” singer discovered he allegedly cheated on her.
According to TMZ, she learned of the existence of a video showing Lucado “making out with a woman and dancing with her.”
Britney later confirmed the breakup on Twitter, writing in 2014, “Ahhhh the single life!”
Charlie Ebersol
In October 2014, Britney began dating Charlie Ebersol, the son of “Saturday Night Live” co-creator Dick Ebersol.
“I thought he was really adorable,” she told People in 2015.
“There was something about him that made me feel really peaceful and at ease,” she went on.
“And he was really hot, too. Adorably hot.”
Sadly, just a couple of months after Britney’s gushing quotes, the two called it quits.
A source claimed to Us Weekly that Charlie was dating her “for the wrong reasons.” The singer scrubbed him from her Instagram shortly afterward.
Sam Asghari
The Grammy winner started dating Asghari after they met on the set of her “Slumber Party” music video in 2016.
“Sam has been a huge support for Britney,” a source told Page Six in June 2021. “He helps boost her confidence.”
The lovebirds continued dating through the COVID-19 pandemic and eventually got engaged in September 2021.
They tied the knot in the backyard of her Thousand Oaks, Calif., mansion in June 2022, with stars like Madonna, Selena Gomez, Paris Hilton and Drew Barrymore on hand to watch the couple exchange vows.
Just one year later, however, reports emerged that the fitness trainer filed for divorce from the pop star amid allegations of infidelity.
According to TMZ, Asghari cited “irreconcilable differences” in the August 2023 filing and is also asking for the star to pay spousal support and his attorneys’ fees.
He listed their separation date as July 28, 2023.
