Talent Recap

Britney Spears’ Dating History: All of The Princess of Pop’s Public Relationships

Justin Timberlake and Britney Spears at "Crossroads" premierePhoto by Jeff Kravitz/FilmMagic

Reading Time: 5 minutes

The Princess of Pop, Britney Spears has always been in the spotlight, and that includes her romantic relationships. From her high-profile romance with Justin Timberlake to her marriages to Kevin Federline and Sam Asghari, Spears’ love life has often made headlines. In her recent memoir, The Woman in Me, the iconic singer has offered a candid look at her past relationships and the ups and downs she’s experienced.

All of Britney Spears’ Public Relationships

Justin Timberlake

Spears’ known dating history began in the late ’90s when she started dating fellow pop sensation, Justin Timberlake. The two first crossed paths as kids on The Mickey Mouse Club and began dating in 1999. Timberlake has described falling for Spears almost instantly, saying, “I was in love with her from the start.”

In her memoir, Spears reminisced about their early romance, including a memorable moment at a sleepover when Timberlake kissed her during a game of Truth or Dare. Their relationship became a fixture on red carpets and in tabloids, with the couple famously wearing matching denim outfits to the 2001 American Music Awards.

However, in 2002, the world was shocked when the pop power couple announced their breakup. Rumors of infidelity circulated, with speculation that Spears had cheated with choreographer Wade Robson, although this was never officially addressed at the time. In her memoir, Spears confirmed that she had kissed Robson while still dating Timberlake.

Colin Farrell

In January 2003, Spears was spotted kissing actor Colin Farrell at a Los Angeles nightclub. Days later, they were seen locking lips on a balcony at the Chateau Marmont in Hollywood. At the time, Farrell downplayed the romance, calling Spears a “mate” and emphasizing that they were just having fun.

In her memoir, Spears gave a more candid account of her two-week fling with Farrell, describing their relationship as a passionate “brawl” where they were “grappling so passionately it was like we were in a street fight.” Despite their intense connection, Spears tried to avoid getting too attached to Farrell because she was still not over Timberlake.

Jason Alexander

In January 2004, Spears shocked the world by marrying her childhood friend, Jason Allen Alexander, in a hasty Las Vegas wedding. The ceremony took place at the Little White Wedding Chapel, with Spears wearing jeans and a baseball cap. The wedding was famously annulled just 55 hours later.

In her memoir, Spears clarified that she and Alexander were not in love. She explained that the decision to get married was influenced by alcohol and boredom rather than genuine romantic feelings. She also revealed that her parents were not pleased with the impromptu nuptials and that the media’s reaction to the wedding was overwhelming.

Kevin Federline

Spears’ relationship with Kevin Federline began when they met at a club in 2004. For Federline, it was love at first sight, and he described being madly in love with her from the beginning. The couple’s romance moved quickly, and they decided to tie the knot after just three months of dating. They surprised everyone with a wedding on September 18, 2004, changing their original wedding date to avoid media scrutiny.

The couple welcomed two sons, Sean Preston and Jayden James, in 2005 and 2006, respectively. However, their happiness was short-lived, and Spears filed for divorce in November 2006, citing irreconcilable differences.

Isaac Cohen

In early 2007, Spears was briefly linked to model Isaac Cohen. Their relationship didn’t last long, and they parted ways in February of the same year. Their split was described as amicable, with both individuals being focused on their respective careers.


Adnan Ghalib

Paparazzo Adnan Ghalib claimed to be in a romantic relationship with Spears in December 2007, even while he was still married. Ghalib’s photo agency, FinalPixx, published exclusive photos of him and Spears, including their vacation to Mexico. The relationship became public knowledge the same day Ghalib’s wife filed for separation, with Ghalib insisting that their love was “far from over.”

Just over a year later, in March 2009, Jamie Spears obtained a restraining order against Ghalib, preventing him from seeing or contacting the pop star for three years.

J.R. Rotem

Following her breakup with Ghalib, Spears briefly dated music producer J.R. Rotem later in 2007. Their relationship was relatively short-lived, but Rotem spoke highly of working with the pop superstar. He praised her professionalism and talent, highlighting her unique qualities as an artist.


Jason Trawick

In 2009, Britney Spears began dating her agent, Jason Trawick. The couple was officially dating, with sources confirming their relationship. Trawick recalled that Spears made the first move, and after two years together, he proposed to her in December 2011. At Britney’s request, he was named a co-conservator alongside her father.

However, the engagement didn’t last, and in January 2013, the couple mutually decided to call it off. They emphasized their intention to remain friends and expressed their continued affection for each other.

David Lucado

In March 2013, Spears began dating David Lucado, whom she met at a party. The relationship was full of passion, and Spears openly declared her love for him. However, their relationship took a turn when discovered a video of Lucado kissing another woman. The betrayal led to their breakup in August 2014.


Charlie Ebersol

Producer Charlie Ebersol, son of Saturday Night Live co-creator Dick Ebersol, began dating Spears in October 2014. Their relationship was characterized as new and slow-moving. Spears was smitten by Ebersol, and they appeared to have a strong connection. However, their romance came to an end in June 2015, with Ebersol reportedly heartbroken by the breakup.

Sam Asghari

Spears met Sam Asghari in 2016 on the set of her “Slumber Party” music video. Despite finding his phone number in her bag five months later, their romance quickly blossomed after they went Instagram official in January 2017. Asghari provided support during difficult times in Spears’ life, including her father’s illness and her mental health treatment in 2019.

Their relationship grew stronger, leading to an engagement in September 2021. The couple married in June 2022 in Los Angeles, surrounded by 60 guests, including celebrities like Madonna, Paris Hilton, Drew Barrymore, and Selena Gomez.

However, just one year after their wedding, Asghari filed for divorce in July 2023. He shared the news on his Instagram Story, expressing respect and love for Spears while acknowledging their decision to part ways.

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