Britney Spears’ Dating History: From Kevin Federline to Sam Asghari

Credit: Getty Images

Britney Spears’ Dating History: From Kevin Federline to Sam Asghari

When you're as iconic as Britney Spears, it's hard to keep your love life under wraps. The singer had a high-profile romance with Justin Timberlake years after they met while filming The Mickey Mouse Club in the '90s. The couple confirmed their romance in 1999 and later split in 2002. Their breakup, just like their relationship, made headlines when Timberlake released “Cry Me a River." In 2021, the documentary Framing Britney Spears explored how Timberlake's behavior after their breakup led to further speculation that Spears cheated on him. Fans rushed to defend Spears' image and called for the "Rock Your Body" singer to apologize for his part in the situation. “I’ve seen the messages, tags, comments, and concerns and I want to respond,” Timberlake wrote in a statement via 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.” Timberlake then apologized to Spears and Janet Jackson for the role he played in their images being affected. “I have not been perfect in navigating all of this throughout my career. I know this apology is a first step and doesn’t absolve the past," he continued. "I want to take accountability for my own missteps in all of this as well as be part of a world that uplifts and supports. I care deeply about the wellbeing of the people I love and have loved. I can do better and I will do better.” At the time, a source told Us Weekly that “Britney does not hold a grudge against Justin over anything he’s said or done.” “She feels that they were young and in love and both did stupid things when they were together. She was heartbroken when they separated, but it’s not something she dwells on now. She’s happy and happy for him," the insider added. Spears went on to have a number of relationships, even briefly getting married to Jason Alexander for 55 hours in 2004, before announcing her engagement to backup dancer Kevin Federline that same year. The pair got married in September 2004. They later welcomed son Sean Preston in September 2005 and Jayden in September 2006. The duo got divorced one year later. [jwplayer 01giRxJq] Following her split from Federline and amid personal issues, Spears was placed under a conservatorship in February 2008. The dancer started dating Sam Asghari after meeting on the set of her “Slumber Party” music video in 2016. After several years together, a source confirmed to Us that the twosome were getting serious. “Sam would love to start a family with Britney,” a source said in March 2021. “He’s always dreamt of having children and thinks he would be a great father. He’s a natural around little kids.” The insider added that Asghari was looking forward to a serious future with Spears, who he preciously gushed about on social media. “Sam also sees marriage in his and Britney’s future when the time is right and they are able to wed without the restraints of her conservatorship and with the blessing of her family,” the source told Us. “He’s very old-fashioned in that way.” During her conservatorship hearing in June 2021, Spears spoke out about wanting control of her body and over the decision to expand her family. "I want to be able to get married and have a baby," she revealed at the time. "I was told right now in the conservatorship, I’m not able to get married or have a baby, I have an IUD inside of myself right now so I don’t get pregnant. I wanted to take the IUD out so I could start trying to have another baby. But this so-called team won’t let me go to the doctor to take it out because they don’t want me to have children — any more children." Scroll down for the singer's complete dating history:

Credit: Getty Images

Britney Spears’ Dating History: From Kevin Federline to Sam Asghari

When you're as iconic as Britney Spears, it's hard to keep your love life under wraps. The singer had a high-profile romance with Justin Timberlake years after they met while filming The Mickey Mouse Club in the '90s. The couple confirmed their romance in 1999 and later split in 2002. Their breakup, just like their relationship, made headlines when Timberlake released “Cry Me a River." In 2021, the documentary Framing Britney Spears explored how Timberlake's behavior after their breakup led to further speculation that Spears cheated on him. Fans rushed to defend Spears' image and called for the "Rock Your Body" singer to apologize for his part in the situation. “I’ve seen the messages, tags, comments, and concerns and I want to respond,” Timberlake wrote in a statement via 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.” Timberlake then apologized to Spears and Janet Jackson for the role he played in their images being affected. “I have not been perfect in navigating all of this throughout my career. I know this apology is a first step and doesn’t absolve the past," he continued. "I want to take accountability for my own missteps in all of this as well as be part of a world that uplifts and supports. I care deeply about the wellbeing of the people I love and have loved. I can do better and I will do better.” At the time, a source told Us Weekly that “Britney does not hold a grudge against Justin over anything he’s said or done.” “She feels that they were young and in love and both did stupid things when they were together. She was heartbroken when they separated, but it’s not something she dwells on now. She’s happy and happy for him," the insider added. Spears went on to have a number of relationships, even briefly getting married to Jason Alexander for 55 hours in 2004, before announcing her engagement to backup dancer Kevin Federline that same year. The pair got married in September 2004. They later welcomed son Sean Preston in September 2005 and Jayden in September 2006. The duo got divorced one year later. [jwplayer 01giRxJq] Following her split from Federline and amid personal issues, Spears was placed under a conservatorship in February 2008. The dancer started dating Sam Asghari after meeting on the set of her “Slumber Party” music video in 2016. After several years together, a source confirmed to Us that the twosome were getting serious. “Sam would love to start a family with Britney,” a source said in March 2021. “He’s always dreamt of having children and thinks he would be a great father. He’s a natural around little kids.” The insider added that Asghari was looking forward to a serious future with Spears, who he preciously gushed about on social media. “Sam also sees marriage in his and Britney’s future when the time is right and they are able to wed without the restraints of her conservatorship and with the blessing of her family,” the source told Us. “He’s very old-fashioned in that way.” During her conservatorship hearing in June 2021, Spears spoke out about wanting control of her body and over the decision to expand her family. "I want to be able to get married and have a baby," she revealed at the time. "I was told right now in the conservatorship, I’m not able to get married or have a baby, I have an IUD inside of myself right now so I don’t get pregnant. I wanted to take the IUD out so I could start trying to have another baby. But this so-called team won’t let me go to the doctor to take it out because they don’t want me to have children — any more children." Scroll down for the singer's complete dating history:

Credit: Getty Images

Britney Spears' Love Life

When you're as iconic in the entertainment industry as Britney Spears, it's hard to keep your love life under wraps. And the pop princess has definitely had her fair share of famous boyfriends — do the names Justin Timberlake, Fred Durst, K-Fed and Criss Angel ring a bell?

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Reg Jones (1995-1997)

Before she was a big deal in the pop music scene, Spears was just a regular teen growing up in rural Louisiana. And her boyfriend at 14 was a guy by the name of Reg Jones who, as Us Weekly would reveal years later, was the one Spears lost her virginity to. Spears' lawyer Eric Ervin admitted to Us that Spears' "virgin" image was a "PR blitz." So much for that!

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Justin Timberlake (1998-2002)

They seemed like a match made in Mickey Mouse Club heaven, but when Justin Timberlake and Britney Spears decided to pull the plug on their picture-perfect Hollywood relationship in 2002 after four years of dating, things didn't quite end on a sweet note. Timberlake would go on to write his hit "Cry Me a River," reportedly about Spears' infidelity, and the pair would drift apart over the years.

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Wade Robson (2001-2002)

When Spears split from Timberlake in 2002, rumor had it that she had been secretly hooking up with dance choreographer Wade Robson behind his back. The pair ended up dating for about a year, and their relationship marked her "not so innocent" period of rebellion.

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Fred Durst (2003)

After splitting from Wade Robson, Spears was linked to a number of familiar names in the music and Hollywood scenes. Limp Bizkit frontman Fred Durst was one of those names, though Spears has denied that the two had a relationship. "It just became a fiasco of madness," Durst told MTV of their split. "[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."

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Jared Leto (rumored; 2003)

The rumor mill really started churning later that year, with Spears reportedly dating Jared Leto at one point — which would have wreaked all kinds of Tinsel Town havoc since Spears' ex Justin Timberlake was dating Leto's ex Cameron Diaz at the time. The singer laughed off the rumors, however, saying that she and the actor were just "really good friends."

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Colin Farrell (2003)

And that's how rumors get started. Spears and Irish actor (and notorious bad boy) Colin Farrell got tongues wagging at the red carpet premiere of his film The Recruit when they showed up together and were later spotted smooching on the balcony of his hotel room. But Farrell denied that the two were in a relationship, insisting that he was "just a 26-year-old guy who's single and having a good time."

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Columbus Short (2003)

There's just something about dancers and their moves! Shortly after being linked to Colin Farrell, Spears was snapped locking lips with one of her backup dancers, a man by the name of Columbus Short. Too bad his loose lips led him to confess his snuggle fest with Spears to a supermarket tabloid — thus ending his marriage and his employment under Spears.

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Jason Alexander (m., 2004)

Spears said "I do" twice in 2004 — but her first marriage was short-lived, even by Hollywood standards. The pop songstress married childhood pal Jason Alexander at the Little White Wedding Chapel in Las Vegas after a long night of partying, but the pair came to their senses shortly afterward and annulled their union after just 55 hours.

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Kevin Federline (m., 2004-2007)

Later that year, at just 22, Spears fell for and married backup dancer Kevin Federline, with whom she had her two sons — Jayden James and Sean Preston Federline. It was around this time, however, that Spears' career began to take a nosedive and she and Federline ended up pulling the plug on their marriage just three years later, in 2007.

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J.R. Rotem (2007)

After her divorce from Kevin Federline, Spears didn't stay single for long, dating music producer J.R. Rotem soon afterward in 2007. The immediacy with which Spears rebounded from Federline had some speculating that Spears had actually been seeing Rotem while she was still a married woman.

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Isaac Cohen (2007)

Spears' next fling was L.A. model Isaac Cohen. The pair were first spotted together while powerboating off Marina Del Ray, Calif. and fans quickly drew comparisons between Cohen and Spears' ex Kevin Federline due to their similar fashion sense. Though Spears and Cohen spent plenty of time together during their whirlwind romance, their busy lifestyles ultimately got in the way of anything more serious and they amicably called it off.

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Howie Day (2007)

Spears entered rehab in February 2007, and — in true Britney fashion — she didn't stay single for long. The pop songstress reportedly began dating singer/songwriter Howie Day shortly after the pair met at the Promises rehab center in Malibu, Calif. but a concerned Lynne Spears reportedly tried to end the relationship after learning that Day had previously been arrested.

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Criss Angel (rumored; 2007)

Following her relationship with Day, Spears was linked to illusionist Criss Angel, but the performer denied that their relationship was anything beyond purely professional. Angel acknowledged that he was helping Spears with her MTV Video Music Awards performance, but said their collaboration stopped there. The shaggy-haired magician had previously been spotted with Paris Hilton and Cameron Diaz.

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Adnan Ghalib (2007-2008)

Spears was getting hounded by the paparazzi nonstop at the height of her very public meltdown, but one photographer in particular seemed to catch the pop star's attention. In December 2007, Spears surprised friends, family and fans when she stepped out with paparazzo Adnan Ghalib. In October 2012, the photographer testified in a heated trial between Spears' former "manager" Sam Lufti and her family.

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Jason Trawick (2009-2013)

One of Spears' most stable relationships was with former manager Jason Trawick. The pair began dating in 2009 and even got engaged in December 2011; unfortunately, they never made it down the aisle. In January 2013, the couple surprised fans by announcing their decision to split, and sources told Us Weekly that the the romance simply fizzled out over time. "Everyone knew Jason was leaving her but Britney," a source told Us. "She's in la-la land."

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David Lucado (2013-2014)

In March 2013, just after Spears’ split from Trawick, Spears was spotted with a new man, lawyer David Lucado. The relationship lasted just over a year: In August 2014, Spears’ rep confirmed their breakup to Us Weekly. “Ahhhh the single life!” the singer tweeted at the time.

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Charlie Ebersol (2014-2015)

Spears got together with Charlie Ebersol — a producer and the son of Saturday Night Live cocreator Dick Ebersol — in October 2014. But in June 2015, Us Weekly exclusively revealed they split, with a source claiming he was in it “for the wrong reasons.” In the wake of the breakup, Spears purged photos of him from her Instagram account.

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Sam Asghari (2016-present)

The pop star met Sam Asghari in October 2016 when he appeared in her “Slumber Party” music video. “I was excited that I [would] get to meet one of the biggest artists of all time; I had butterflies,” the fitness model recalled in a July 2018 Men's Health interview. “She motivates me more than anyone. I’m always going to support her. She is another blessing that happened to me.” 

In September 2021, the couple announced their engagement via Instagram. “The couple made their long-standing relationship official today and are deeply touched by the support, dedication and love expressed to them," Asghari's manager told Us in a statement at the time.

The twosome wed in June 2022 surrounded by 100 star-studded guests. However, a source told Us that Spears’ family was not in attendance.