From Justin Timberlake to Kevin Federline: Look back at Britney Spears’ relationship history

Justin Timberlake

Spears dated former NSYNC member Justin Timberlake from 1999 to 2022.

The pop power couple first met as 11-year-olds on the set of The Mickey Mouse Club in 1992.

Spears and Timberlake confirmed their romance in 1999, with the couple dating until March 2002.

“I remember when we decided we were going to go out separate ways, we sat down and I said to her if there’s ever a moment where you ever need me, you can rest assured that I will be there, because I love you as a person and I will always love you,” Timberlake previously stated in an interview with Barbara Walters.

Wade Robson

Spears was rumoured to be linked with Australian dancer and choreographer Wade Robson from 2001 to 2002.

Information surrounding the couple’s potential romance stems from Michael Jackson’s niece Brandi, who was previously in a relationship with Robson.

In the documentary Neverland Firsthand: Investigating the Michael Jackson Documentary, Brandi alleges that Robson had cheated on her with Britney Spears while the star was touring. She also speculates that this rumoured affair was responsible for Spears’ split with Justin Timberlake in 2002.

Fred Durst

Limp Bizkit frontman Fred Durst had a brief relationship with Britney Spears in 2003.

Although their romance was brief, Durst was scathing in his comments on the relationship, telling The Sydney Morning Herald, “She’s definitely not the sweet, innocent little thing… She definitely parties too much. She drinks and smokes so much much. I think it’s something she’s picked up on. She’s got a crazy life.”

“Once again, it’s Fred playing kiss and tell. Only Fred’s doing a lot more talking than he ever did kissing. This whole situation is very junior high school,” Spears’ spokeswoman told the publication.

Jared Leto

It has been rumoured that Spears was in a romantic relationship with actor and Thirty Seconds to Mars frontman Jared Leto in early 2003, following the two being spotted together.

Neither party have confirmed the speculation, with Leto reportedly commenting that the duo were just good friends at the time.

Colin Farrell

Britney Spears was rumoured to be romantically involved with Irish actor Colin Farrell after the pair were reportedly caught kissing at the 2003 premiere of The Recruit.

Both Spears and Farrell have not yet commented on the speculation however, according to The Sun, it has been rumoured that Farrell has expressed legal concern over alleged details of their relationship in Spears’ upcoming memoir.

Columbus Short

Spears was first linked to her back-up dancer Columbus Short in 2003, with rumours of their relationship beginning to surface following a paparazzi photo of the couple kissing.

Short has since spoken publicly on their brief romance, alleging that Spears’ parents used a racial slur to describe him during a phone conversation.

“After that, I felt like maybe Briney was using me to piss them off for some reason. I think she is a really sweet person that was tormented in a position on a high level that I can’t imagine,” he told Inside Hollywood’s Jazzie Belle.

Jason Alexander

Britney Spears and Jason Alexander married in Las Vegas in 2004, with the couple annulling their nuptials 55 hours later.

In June 2022, Alexander was convicted of trespassing and battery after he made an unannounced appearance at Spears’ wedding to her long-time partner Sam Asghari.

“She’s my first wife, my only wife,” Alexander stated in his Instagram Live video of the incident. The video depicted Alexander walking through Spears’ home before heading to her wedding marquee that was also on her property.

Kevin Federline

Spears began dating dancer and rapper Kevin Federline in April 2004.

The couple married on September 18, 2004, with the couple welcoming their son Sean in September 2005 and Jayden in September 2006.

According to TMZ, Spears filed for divorce from Federline in November 2006; citing irreconcilable differences.

The couple were subsequently involved in a highly publicised custody battle, with Federline being granted sole legal and physical custody of their two children.

Criss Angel

Spears was rumoured to be involved with magician Criss Angel in 2007, following the pair being spotted together on multiple occasions.

Angel previously told OK! that the duo had been working together on a concept for Spears’ live performance of Gimme More for the MTV Video Music Awards.

While Angel didn’t comment on their alleged romance, he confirmed at the time that the pair were still close friends.

Adnan Ghalib

Britney began dating paparazzi photographer Adnan Ghalib in 2007.

The couple were together for one year, with Spears filing a restraining order against for the photographer in March 2008; claiming that he had been conspiring to interfere with her personal affairs.

Jason Trawick

Spears began her manager Jason Trawick in 2009, with the couple announcing their engagement in 2011.

Unfortunately for the couple, they did not get to tie the knot, with Spears and Trawick announcing they had parted ways in 2013.

During their relationship, Trawick was also briefly appointed as the co-conservator of Britney’s person after the couple became engaged.

“Did she need a conservatorship when I was there? Yes. I’ll be the first to say it. I think she needed some guidance,” Trawick told Kevin Connelly.

David Lucado

Lawyer David Lucado and Britney Spears first confirmed their relationship in March 2013.

The couple were together for just over a year, with the pair going their separate ways following a leaked video of Lucado kissing another woman was published by TMZ.

“Ahhh the single life!,” Spears tweeted in August 2014, confirming the couple were no longer together.

Charlie Ebersol

Charlie Ebersol, who is the son of Saturday Night Live creator Dick Ebersol, began dating Britney Spears in October 2014.

The couple were reportedly together for eight months before going their separate ways, with their last public appearance as a couple being at the 2015 Billboard Music Awards.

Sam Asghari

Britney Spears is currently in a relationship with model Sam Asghari.

The couple first met in 2016 on set of her Slumber Party music video. “I was excited that I get to meet one of the biggest artists of all time. I had butterflies,” Asghari previously told Men’s Health.

The couple announced their engagement via Instagram in September 2021, with the couple marrying in June 2022.