From Justin Timberlake to Sam Asghari: A timeline of Britney Spears’ relationships

In her forthcoming memoir, The Woman in Me, Britney Spears is expected to reflect on some of the most pivotal moments in her life, including her relationships.

Over the years, the pop star’s love life has continued to make headlines. Most recently, her ex-husband Sam Asghari filed for divorce after only 14 months of marriage. Spears is also the mother of two children – Sean, 18, and Jayden, 17 – who she shares with her second ex-husband, Kevin Federline.

According to a press release for The Woman in Me, Spears’ memoir is “a brave and astonishingly moving story about freedom, fame, motherhood, survival, faith, and hope”. Spears’ book is also expected to cover the high-profile legal battle to end her conservatorship, which was dissolved in November 2021 after 13 years.

Throughout her time in the spotlight, specifically during the ‘90s and 2000s, Spears has been in some heavily publicised romances. Unsurprisingly, fans are anticipating that Spears will detail some of her relationships in The Woman in Me, which is set for release on 24 October.

From Justin Timberlake to her now ex-husband Sam Asghari, here’s everything we know about Britney Spears’ relationships and rumoured romances.

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Spears’ first highly public relationship was with her co-star in the Mickey Mouse Club, Justin Timberlake. The pair made many appearances together while dating, including the iconic moment Spears and Timberlake wore matching, all-denim outfits to the American Music Awards in 2001.

They broke up in 2002, shortly after Timberlake and his boy band NSYNC released their hit tune, “Cry Me a River”. At the time, the music video for the song – which featured a woman with blonde hair - sparked rumours that he and Spears broke up because she allegedly cheated on him.

Although the former couple never acknowledged the breakup rumours, the 2021 Framing Britney documentary addressed some of the public scrutiny that Spears faced during the 2000s. Following the documentary’s release, Timberlake came under criticism for the way he acted following his breakup with Spears.

He later issued an apology to Spears on Instagram, writing: “I’ve seen the messages, tags, comments, and concerns and I want to respond. 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.”

In June 2021, he also shared his support for Spears after she testified publicly in a bid to end her conservatorship, which was controlled by her father, Jamie Spears. In a Los Angeles court hearing at the time, Spears alleged that she had been forced to take lithium against her will. She also claimed that the team managing her conservatorship had prevented her from having another baby by refusing to remove her IUD.

“After what we saw today, we should all be supporting Britney at this time. Regardless of our past, good and bad, and no matter how long ago it was,” Timberlake wrote on X, formerly known as Twitter.  “What’s happening to her is just not right. No woman should ever be restricted from making decisions about her own body.”

Shortly after her breakup from Timberlake, Spears was rumoured to be dating Wade Robson, a dancer and choreographer who appeared in the music video for her 2009 tune, “(You Drive Me) Crazy”. However, neither Spears nor Robson confirmed these rumours.

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Back in 2003, Farrell and Spears made headlines when they were spotted holding hands at the premiere of The Recruit, sparking speculation that they were dating. However, during an interview with Entertainment Tonight at the time, the actor specified that he and the singer were just friends.

“She’s just a mate,” Farrell told the outlet, as reported by People in 2003. “Seriously, we just met a week ago, [we’re] having a laugh.”

Jason Alexander was Spears’ first husband, tying the knot at a wedding chapel in Las Vegas in 2004. However, only 55 hours after the nuptials, they annulled the marriage.

In 2022, Alexander made headlines when he tried to attend Spears’ wedding to Asghari, as could be heard saying in a video that he was going to crash the nuptials. “She’s my first wife, my only wife,” Alexander reportedly told security. “I’m her first husband, I’m here to crash the wedding.”

After he was arrested for trespassing, vandalism, and battery, a security guard later revealed in court that when Alexander crashed the wedding, he also tried to enter Spears’ bedroom.

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Kevin Federline and the “Gimme More” singer first met at a club in 2004, before they went on to start their relationship. After just three months of dating, the two tied the knot in September of that year during a surprise wedding ceremony. Weeks before their one-year wedding anniversary, they welcomed their first child, son Sean Preston.

In 2006, they welcomed their second son, Jayden James. At the time, Federline was already a father to his daughter Kori Madison, now 20, and son Kaleb Michael, 18, with ex-fiancée Shar Jackson.

Spears went on to file for divorce from Federline in November 2006, citing “irreconcilable differences” as the reason for their split. In the couple’s initial divorce settlement, they were granted joint legal and physical custody over their two children. While it appeared they were on good terms after their separation, things took a turn in 2018 when Federline requested an increase of $20,000 a month more child support payments from Spears.

After months of court discussions, Federline rejected Spears’s child support proposal and instead doubled his request to $40k a month. A settlement was finally reached between the two parties in September 2018, with Spears increasing her child support payments to Federline from $20,000 to $35,000 a month.

Federline has since moved on from the relationship, as he married volleyball player Victoria Prince in 2013. They now share two daughters, Jordan, 10, and Peyton, eight.

Spears met British paparazzo Adnan Ghalib in 2007, shortly after she decided to shave her hair off in front of approximately 70 photographers. They only dated for about a year, as the relationship ended in 2008.

In the 2021 Netflix documentary, Britney vs Spears, Ghalib spoke candidly about the romance, claiming: “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.”

The former couple split in 2008 after Ghalib reportedly pulled a pregnancy test-buying stunt for publicity. In 2009, Jamie Spears filed a restraining order against Ghalib, which ordered the photographer to stay away from the singer and her family until 2012.

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Spears and Jason Trawick, a Hollywood agent who worked at WME, started dating in 2009 before getting engaged in December 2011. However, they called off their engagement in January 2013 and announced they were going their separate ways.

"Jason and I have decided to call off our engagement. I’ll always adore him and we will remain great friends," Spears said in a statement sent by her representative to ABC News.

Trawick also issued a statement at the time, saying: “As this chapter ends for us a new one begins. I love and cherish her and her boys and we will be close forever."

Two months after ending her engagement with Trawick, Spears started dating David Lucado, who worked at a legal firm. In August 2014, Spears announced their split, tweeting: “Ahhhh the single life!” At the time, her representative also confirmed to People: “Yes, she’s single.”

The news of the breakup came asTMZ alleged that Lucado had cheated on Spears, with claims that her father had purchased a video of the infidelity incident. The publication later alleged that Lucado denied the cheating allegations, with claims that he was seeing the other woman while he and Spears were broken up.

Despite their seemingly rocky history, Lucado showed his support for his ex in a 2016 interview with theNew York Times about her conservatorship. Speaking to the publication, he said: “If anyone knew the real Britney, they would know that she would rather be remembered for being the great mother she is rather than the artist she is.”

The publication also noted that Lucado denied the infidelity claims from Spears’ father, before he added: “And if anyone could see her interactions with her kids, they would know that there is no need for a conservatorship over Britney’s personal life.”

Spears and Charlie Ebersol, who is known as the co-founder of Tempus Ex Machina and The Company, started dating in 2014. While their relationship was fairly low profile, Spears previously opened up about why she was drawn to Ebersol in the first place.

“There was something about him that made me feel really peaceful and at ease. And he was really hot, too. Adorably hot,” she told People at the time.

They officially broke up in June 2015 after eight months of dating.

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The pair first met in 2016 when Asghari was cast as Spears’ love interest in the music video for her song, “Slumber Party”, from her 2016 album Glory. They made their relationship Instagram official in 2017 and went on to support each other through different milestones - including the 29th annual GLAAD Media Awards, where Spears accepted the Vanguard Award for her work promoting equality and acceptance.

In April 2022, Spears announced she was pregnant with her and Asghari’s first child together, and her third child. However, the following month, she said in a statement posted to Instagram that she had suffered a miscarriage. The couple wrote: “We have lost our miracle baby.”

That June, they held their lavish nuptials at her home in California with a star-studded guest list, which included Selena Gomez, Paris Hilton, Drew Barrymore, and Donatella Versace - who designed Spears’ wedding dress.

In August, months after Asghari shut down speculation about getting a divorce, TMZ claimed that he had confronted Spears about rumours she cheated on him. That same day, the fitness instructor officially filed for divorce, listing the date of separation as 28 July 2023 and citing "irreconcilable differences" as the reason for the split.

In a statement posted online, Asghari said: “After six years of love and commitment to each other my wife and I have decided to end our journey together. We will hold onto the love and respect we have for each other and I wish her the best always. S*** happens. Asking for privacy seems ridiculous so I will just ask for everyone including the media to be kind and thoughtful.”

Days before Spears’ memoir release date, Asghari revealed that he had obtained an early copy of the book. In an interview with TMZ on 13 October, he explained that he wasn’t worried about anything being written in the book that could paint him in a negative light.

“I already read it and I’m very proud of her,” he told the outlet. “She put a lot of work into it, and it was very hard. I’m definitely excited, and I’m extremely proud of her. It was a very tough one [to write].”

The Woman in Me is due for release on 24 October in the US and UK.