Britney Spears' Iconic Love Journey: Unveiling Her Romantic Chapter from Kevin Federline to Sam Asghari

Britney Spears has been at the center of media attention for her love life ever since she gained fame in the 1990s. Her relationships with Justin Timberlake and Sam Asghari have been particularly noteworthy.

Among these relationships, Spears and Timberlake stood out as a power couple during the '90s. However, their breakup in 2002 resulted in a messy situation. Recently, after two decades, Timberlake publicly expressed regret for contributing to the speculation that Spears had been unfaithful to him through his song "Cry Me a River."

"I sincerely apologize for the times in my life when my actions contributed to the issue, when I spoke out of turn or failed to stand up for what was right," Timberlake expressed on Instagram in February 2021, after his involvement with Spears was closely scrutinized in the Framing Britney Spears documentary. "I acknowledge that I fell short in those moments and many others, and benefited from a system that supports misogyny and racism."

In addition to her relationship with Timberlake, Spears' marriages — as well as her divorces — have garnered significant media attention. Following her separation from Kevin Federline in 2007, Spears was placed under a conservatorship in 2008. The legal arrangement came to a conclusion in the autumn of 2021.

Scroll down for the singer’s complete dating history:

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

Britney Spears has been constantly in the spotlight for her love life ever since she emerged in the music industry during the '90s. She has had notable relationships with Justin Timberlake and Sam Asghari.

During the '90s, Spears and Timberlake were widely known as a power couple. However, their breakup in 2002 led to a messy situation. It took two decades for Timberlake to apologize to Spears, acknowledging his contribution to the rumors of her infidelity through his song "Cry Me a River."

"I deeply apologize for the moments in my life where my actions contributed to the issue, where I spoke inappropriately or failed to speak up for what was right," wrote Timberlake on Instagram in February 2021, in response to the scrutiny surrounding his relationship with Spears in the documentary 'Framing Britney Spears'. "I acknowledge that I fell short in those instances, as well as many others, and benefited from a system that tolerates misogyny and racism."

Alongside her association with Timberlake, Spears' marriages and divorces have received significant public attention. Following her separation from Kevin Federline in 2007, Spears was placed under a conservatorship in 2008, which concluded in the autumn of 2021.

Scroll down for the singer’s complete dating history:

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Reg Jones (1995-1997)

Before becoming a prominent figure in the pop music industry, Spears was a typical teenager residing in rural Louisiana. At the age of 14, her boyfriend was Jones, who, as disclosed years later, was the person Spears had her first sexual experience with. Spears' attorney, Eric Ervin, openly admitted to Us that her "virgin" persona had been a strategic public relations campaign.

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Justin Timberlake (1998-2002)

The relationship between Timberlake and Spears appeared to be a match made in Mickey Mouse Club heaven. However, in 2002, after four years of dating, they decided to call it quits. Unfortunately, their breakup was not a pleasant one. Timberlake channeled his emotions into writing his hit song "Cry Me a River," which is said to be about Spears' alleged infidelity. Over the years, the couple grew apart and drifted away from each other.

In her 2023 memoir, titled "The Woman in Me," Spears reflected on her past relationship with Timberlake and shared a personal revelation. She disclosed that she had undergone an abortion because Timberlake was not ready to become a father at that time.

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Wade Robson (2001-2002)

Following her split from Timberlake in 2002, speculation circulated that Spears had been engaged in a covert romantic involvement with choreographer Robson while still being in a relationship with Timberlake. Eventually, Spears and Robson embarked on a year-long romance, signifying a phase of defiance and controlled rebellion for her. In her memoir released in 2023, Spears openly admitted to having been unfaithful to Timberlake with Robson.

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Fred Durst (2003)

Following her breakup with Robson, Spears became romantically linked to several well-known figures in the music and Hollywood industries. Among these names was the frontman of Limp Bizkit. However, Spears firmly denied any romantic involvement with him. Durst spoke about their alleged relationship, describing it as a chaotic ordeal. He stated, "Nevertheless, I always remain true to my heart, my actions, and my intentions, and I am certainly not a dishonest individual."

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Jared Leto (2003)

Speculation went into overdrive in 2003 when reports of Spears being romantically involved with Leto surfaced. Despite the buzz, Spears dismissed the rumors, asserting that she and the actor remained close platonic companions.

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Colin Farrell (2003)

The appearance of Spears and Farrell on the Recruit red carpet in 2003 caused a stir among onlookers. Rumors circulated when they were later seen kissing on the balcony of his hotel room. Nevertheless, Farrell was adamant in denying any romantic involvement and emphasized that he was simply a 26-year-old man enjoying his single status and having a good time.

Spears, meanwhile, detailed the whirlwind romance in her 2023 memoir, claiming, “We were all over each other, grappling so passionately it was like a street fight.”

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Columbus Short (2003)

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Shortly after being associated with Farrell, Spears was photographed sharing a passionate kiss with her backup dancer. Shortly after Short confirmed the kiss, he ended his marriage to Brandi Short and ceased working for Spears.

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Jason Alexander (2004)

Spears tied the knot with her childhood friend Alexander at the Little White Wedding Chapel in Las Vegas in 2004, following a night of extensive celebration. However, their union was promptly annulled a mere 55 hours later.

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Kevin Federline (2004-2007)

Spears tied the knot with backup dancer Federline in 2004, and they became proud parents to two sons: Jayden James in 2005 and Sean Preston in 2006. Unfortunately, Spears and Federline's marriage came to an end in 2007.

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Isaac Cohen (2007)

In 2007, while powerboating off Marina Del Rey, California, Spears was initially seen with the L.A. model. Despite their whirlwind romance and ample time spent together, their hectic schedules hindered the development of a more profound commitment, resulting in a cordial and mutual decision to end their relationship.

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Howie Day (2007)

Spears allegedly started dating the singer shortly after their encounter at the Promises rehab center in Malibu back in 2007. Informed about Day's prior arrest, a worried Lynne Spears attempted to terminate the relationship.

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Adnan Ghalib (2007-2008)

At the peak of her highly publicized breakdown, Britney faced relentless pursuit from the paparazzi. Amongst them, one particular photographer managed to capture her attention. Surprising her friends, family, and fans, she emerged in December 2007 alongside the paparazzo, Ghalib. During a tumultuous trial in October 2012, Ghalib provided vital testimony in the dispute between Britney's former "manager," Sam Lutfi, and her family.

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Jason Trawick (2009-2013)

One of Britney's most enduring partnerships was with her ex-manager. They initiated a romantic relationship in 2009 and even got engaged in December 2011. Regrettably, they never exchanged vows. In January 2013, the couple shocked fans by publicly declaring their separation, and insiders revealed to Us that their love gradually faded away over time.

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David Lucado (2013-2014)

In March 2013, right after her separation from Trawick, Britney was seen alongside lawyer Lucado, with whom she had a relationship that lasted slightly over a year. In August 2014, Britney’s representative confirmed their breakup to Us.

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Charlie Ebersol (2014-2015)

Britney began dating Ebersol, a producer and the son of Saturday Night Live cocreator Dick Ebersol, in October 2014. However, their relationship came to an end in June 2015, as Us exclusively reported. According to a source, the reason for the split was that he had ulterior motives. Following the breakup, Britney removed all the photos of him from her Instagram account.

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Sam Asghari (2016-2023)

Britney and Asghari first crossed paths in October 2016 during the filming of her "Slumber Party" music video. Reflecting on the experience during a Men's Health interview in July 2018, Asghari expressed his excitement and nerves at the prospect of meeting such a renowned artist. He shared that Britney serves as a constant source of motivation and support for him, describing her as a blessing in his life.

Fast forward to September 2021, the couple joyfully announced their engagement on Instagram. Asghari's manager conveyed their gratitude for the overwhelming outpouring of love, dedication, and support from their fans, solidifying their long-standing relationship.

Surrounded by a star-studded group of 100 guests, the couple exchanged vows in June 2022. It is worth noting that Spears' family was absent from the event, according to a source.

Citing irreconcilable differences, Asghari officially filed for divorce from Britney in August 2023. He stated that their separation date was July 28, 2023.