With her upcoming memoir ‘The Woman In Me,’ the ‘Toxic’ singer is expected to share new details about her past romances. Here is a complete timeline of Brit’s dating history!

Britney Spears has been in the spotlight for more than 20 years and on June 9, 2022, the iconic pop star walked down the aisle with longtime boyfriend Sam Asghari. Sadly, just over one year after the duo tied the knot, Britney, 41, and her husband split!

Prior to her romance with Sam, Britney got married twice and engaged three times. She also birthed two sons and had a high-profile romance with Justin Timberlake. Now, with her new memoir The Woman In Me hitting bookshelves on October 24, Britney is expected to shed new light on many of her past relationships. Want to know more? Take a look at this breakdown of her romantic history, below!

Justin TimberlakeBritney Spears and Justin Timberlake at an event together. (AP)

Britney and Justin Timberlake were the ultimate pop music couple when they dated from early 1999 until 2002. At the time, she was at the height of her early career, while he was at the peak of his boy band days in NSYNC. They were together for more than three years when things ended quite abruptly. In her memoir, Britney claimed that Justin cheated on her with “another celebrity,” who remains unnamed. She also admitted to infidelity herself. The singer claimed that she cheated on him with choreographer Wade Robson. 

After the split, Justin went on to release his first solo song, “Cry Me A River,” which he eventually admitted was about his split from Britney. The “Toxic” singer admitted that she felt like she was portrayed unfairly in the song’s music video, in an excerpt from her memoir, per People.

Beside the breakup and cheating rumors, Britney also alleged that she became pregnant during their relationship. She wrote that they got an abortion in an excerpt released by People. “Justin definitely wasn’t happy about the pregnancy. He said we weren’t ready to have a baby in our lives, that we were way too young,” she wrote.

Although they grew apart over the years, they both complimented each other on social media in 2020. With details about their past relationship making headlines before the book’s release, a source explained that Justin was mostly focusing on his own family. “In recent years, Justin has tried to be supportive of Britney from a distance. They dated so long ago, but he still has respect for her. Justin and [wife Jessica Biel] just want everyone to grow and evolve instead of continuing to bring up the past,” an insider told ET. 

Wade RobsonBritney Spears and Wade Robson on separate occasions. (AP Images)

Britney dated choreographer Wade Robson for about a year after her split from Justin. However, there have been widespread rumors that she began hooking up with Wade before ending things with Justin, and Britney seemed to confirm them in her memoir. Robson is one of the men who has accused Michael Jackson of sexual abuse, and his claims were the subject of the 2019 documentary, Leaving Neverland.

Colin FarrellColin Farrell wraps his arm around Britney Spears. (AP Images)

Britney and Colin Farrell sparked major romance rumors when they attended the premiere of The Recruit together in 2003. Later on, they were also spotted making out on his hotel room balcony! However, Colin denied that the two were ever anything serious, and insisted that they were just “having fun.”

Britney opened up about the passionate fling, which she called a “two-week brawl,” in a pre-released excerpt of her memoir. “Brawl is the only word for it—we were all over each other, grappling so passionately it was like we were in a street fight,” she said. “As I had before when I’d felt too attached to a man, I tried to convince myself in every way that it was not a big deal, that we were just having fun, that in this case, I was vulnerable because I wasn’t over Justin yet.”

Columbus ShortBritney Spears dances with Columbus Short onstage.

Shortly after being linked to Colin, Britney hooked up with one of her backup dancers, Columbus Short. The following year, Columbus opened up about the hookup in an interview with Star magazine, and admitted that it led to the demise of his marriage (his wife was pregnant with their first child at the time). Columbus’ employment with Britney was terminated afterward, as well.

Jason AlexanderBritney Spears and Jason Alexander on separate occasions. (SplashNews)

In 2004, Britney shocked everyone when she married her childhood friend, Jason Alexander, at the Little White Wedding Chapel in Las Vegas. However, in one of the most short-lived celebrity marriages of all-time, the pair annulled their union after just 55 hours of wedded bliss. Britney filed a petition with the court, which stated that she “lacked understanding of her actions” at the time of the nuptials.

In a shocking turn of events, Jason was arrested on June 9, 2022 after he tried to crash Britney’s wedding to Sam. In a video on his Instagram Live, Jason filmed himself trying to sneak into the pop star’s wedding in Thousand Oaks, CA as police arrested him.

Kevin FederlineBritney Spears and Kevin Federline out and about together. (SplashNews)

That same year, Britney met backup dancer, Kevin Federline. Just three months after they met, the two were engaged, and they tied the knot in September 2004 (although the nuptials were not legalized until a few weeks later). At the time all of this was happening, Kevin’s ex, Shar Jackson, was pregnant with his second child. Britney and Kevin wound up having two sons of their own: Sean Preston was born in Sept. 2005, followed by Jayden James in 2006. As Britney began dealing with some issues with her mental health, her relationship with Kevin fizzled out, and they split in 2006. The divorce was finalized in July 2007.

J.R. RotemBritney Spears out and about with J.R. Rotem. (SplashNews)

Following her divorce from Kevin, Britney didn’t take long to get back on the dating scene. She briefly dated music producer J.R. Rotem in 2007, although there was some speculation that their relationship potentially began while she was still with Kevin. Again, this has not been confirmed by either party.

Adnan GhalibBritney Spears on an escalator with Adnan Ghalib.

Britney shocked her friends, family and fans when she got together with a paparazzo at the end of 2007. She briefly dated photographer, Adnan Ghalib, despite the fact that she was being hounded by paparazzi for months. Although the relationship was short-lived, Adnan re-entered Britney’s life in 2012 when he testified in Sam Lutfi’s case against the singer (Sam sued Britney for unpaid fees and accused her father, Jamie, of punching him).

Jason TrawickBritney Spears at an event with Jason Trawick. (SplashNews)

After these flings, Britney got into another long term relationship beginning in 2009, when she started dating her manager, Jason Trawick. The pair’s relationship was confirmed in 2010, and in December 2011, the two got engaged. Jason even became a co-conservator for Britney and obtained legal control of the singer. Unfortunately, the relationship eventually fizzled out, and Britney and Jason split at the beginning of 2013. At that time, he was removed as her conservator.

David LucadoBritney Spears holds hands with David Lucado. (SplashNews)

Following the end of her engagement to Jason, Britney began dating a lawyer, David Lucado, in 2013. However, the romance lasted just one year, and by 2014, the two had broken up. At the time, it was reported that Britney ended the relationship because she caught David kissing another woman, but those rumors have not been confirmed.

Charlie EbersolBritney Spears and Charlie Ebersol cozy up on the red carpet. (SplashNews)

Brit’s next relationship was with Charlie Ebersol, who works as a producer and is the son of Saturday Night Live‘s co-creator, Dick Ebersol. They got together in 2014 and even made public appearances on red carpets together. However, the relationship ended in 2015.

Sam AsghariBritney Spears and Sam Asghari on the red carpet. (MEGA)

Britney met her current husband, Sam Asghari, on the set of her music video for “Slumber Party” in 2016. Despite an age difference of more than ten years, the two hit it off and exchanged numbers after the shoot. They started seeing each other afterward, and went Instagram official in January 2017. Ever since, Sam has been a rock for Britney — he was a solid support system when she sought out mental health resources in 2019.

Sam spoke out about his relationship with Britney, and the pop star’s father, Jamie Spears‘, involvement in her conservatorship — instituted roughly 12 years ago. “Now it’s important for people to understand that I have zero respect for someone trying to control our relationship and constantly throwing obstacles in our way,” Sam shared on his Instagram Story. “In my opinion, Jamie [Spears] is a total d*ck.” The statement came just days following the premiere of The New York Times‘ documentary Framing Britney Spears premiered on FX and was later viewed by fans on Hulu.

After Sam proposed to Britney in September 2021, the pair got hitched in a surprise wedding on June 9, 2022!  In front of a small group of friends — including Drew Barrymore, Paris Hilton and Selena Gomez — the couple said ‘I do’ with Sam getting silly at the reception afterwards by wearing Britney’s veil. He also sported a custom T-shirt reading ‘BRITNEY & SAM’ on the front as the couple left their special event in a Rolls Royce.

After only a year of marriage, it was revealed that the pair had split up in August 2023. Amid the split, Sam said he wouldn’t challenge the prenup that they had in place. Shortly after the breakup was reported, Sam shared a brief statement on Instagram. “We will hold onto the love and respect we have for each other and I wish her the best always,” he wrote.

A few days after the divorce made headlines, Britney released her own statement on Instagram. “As everyone knows, Hesam and I are no longer together … 6 years is a long time to be with someone so, I’m a little shocked,” she wrote. “I couldn’t take the pain anymore honestly!!! In some sort of telepathic way I have been receiving so many messages that melt my heart from friends and I thank you.”