Who Has Britney Spears Dated? Look Back at Her Former Flames
Britney Spears once said that, despite her superstar status, dating can be a real challenge. But that doesn't mean she hasn't had her fair share of romances. While the young love Spears and Justin Timberlake once shared may be her most notable romance to date, you may have forgotten that she also dated former Hollywood bad boy Colin Farrell and even married her high school boyfriend Jason Alexander.
During her "Carpool Karaoke" session with James Corden back in August 2016, the singer said, "I think I might not ever go to men again, do the whole men thing anymore, or get married. I'm just done with men . . . I'm not going to marry someone. No, I don't believe in marriage anymore."
Well, it seems Spears had a change of heart, because she then moved on with Sam Asghari, whom she married in June 2022. Their marriage only lasted a year, however, since Asghari filed for divorce from the pop star in August 2023. Not much else is known about their separation, but perhaps Spears will shed some light in her new memoir "The Woman in Me," out Oct. 24.
In the meantime, keep reading for a look at Spears's former flames.
After meeting on the set of "The Mickey Mouse Club" as kids, Spears and Timberlake began dating in 1999, though they didn't go public with their romance until a year later. The two eventually parted ways in 2002 following rumors that Spears cheated on him with choreographer and frequent collaborator Wade Robson.
According to People, Spears reveals in her upcoming memoir, "The Woman in Me," that she got pregnant with Timberlake's baby when they dated and had an abortion.
"It was a surprise, but for me, it wasn't a tragedy. I loved Justin so much. I always expected us to have a family together one day. This would just be much earlier than I'd anticipated," Spears writes of the pregnancy in the book, per the publication. "But 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."
Timberlake's rep did not immediately respond to POPSUGAR's request for comment.
Shortly after her split from Timberlake, Spears moved on with her dance choreographer, though several sources claimed that the two had been hooking up when she was still dating Timberlake, per Us Weekly. Spears and Robson reportedly carried on a relationship for about a year before eventually calling it quits in 2002.
In 2003, Spears had a brief fling with the former Hollywood bad boy, according to E! News. The stars only went out on one date, and Farrell said he was "just a 26-year-old guy who's single and having a good time."
While Spears denies ever having a relationship with the Limp Bizkit singer, Durst reportedly dated Spears in 2003, according to People. During that time, Durst raved about their romance on his band's website, saying that he had "never felt this way."
However, Spears told Glamour UK (via Today) that the relationship was one-sided, adding, "He's said some pretty amazing things about me, but, um, I think he leaped in too deep, too quick."
In 2009, Durst opened up about their rumored romance once again, telling MTV News, "It just became a fiasco of madness . . . [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."
The "Gimme More" singer wed her high school boyfriend at the Little White Wedding Chapel in Las Vegas in 2004, but the marriage was annulled after just 55 hours.
Six months after annulling her marriage to Alexander, Spears moved on with her backup dancer, who was still married to actor Shar Jackson at the time. After dating for a few months in 2004, the duo tied the knot in a surprise unofficial ceremony — they didn't have a prenup agreement, so it wasn't official for three weeks, per Us Weekly.
The pair welcomed two sons together, Jayden James and Sean Preston, and even went on to have their own reality show on UPN called "Britney and Kevin: Chaotic." However, as Spears's career took a turn for the worse, the two ended up pulling the plug on their marriage and split in October 2006, though their divorce wasn't finalized until July 2007.
While in the middle of her public meltdown in 2007, Spears shocked fans when she began dating the photographer. Their relationship only lasted a year, and officially ended when Spears filed a restraining order against him, claiming he was conspiring to take control of her affairs, per Rolling Stone.
In 2012, Ghalib testified in a trial between Spears's former manager, Sam Lutfi, and her family, claiming Spears's mother once tried to coerce him, saying, "She requested that I say [to the media] Sam Lutfi was responsible for Britney Spears's behavior," according to People. The photographer also admitted that a judge ordered him to stay away from the singer for three years.
Spears started dating her former manager in early 2009, and the two got engaged in December 2011, per Today. The singer confirmed the news with a tweet, writing, "OMG. Last night Jason surprised me with the one gift I've been waiting for. Can't wait to show you! SO SO SO excited!"
However, they never made it down the aisle and instead broke up in January 2013. Spears issued a statement to E! News, saying, "Jason and I have decided to call off our engagement. I'll always adore him and we will remain great friends."
Months after her split from Trawick, Spears was photographed with a new man, who was later identified as David Lucado, per E! News. Lucado was a normal guy from the South, and the two dated for over a year in 2013. Spears seemingly confirmed their breakup in August 2014 when she tweeted out a cryptic status that read, "Ahhhh the single life!"
In 2014, the mother of two began dating Ebersol, a TV producer from a Hollywood family. Spears confirmed the romance by sharing photos of the two on Instagram and making their red carpet debut at the Billboard Music Awards, but alas, their relationship came to an end just eight months later.
Spears first met the dancer on the set of her "Slumber Party" music video in 2016. While it's unclear when these two officially started dating, the couple seemingly confirmed their romance in November 2016 when Asghari posted an Instagram photo of him and Spears enjoying a romantic sushi dinner.
In September 2021, the couple got engaged. Asghari's manager told Us Weekly in a statement, "The couple made their long-standing relationship official today and are deeply touched by the support, dedication, and love expressed to them."
Almost a year later, the pair tied the knot in a small wedding at Spears's Los Angeles home on June 9, 2022. However, their marriage was short-lived as Asghari filed for divorce from Spears a year later, citing "irreconcilable differences" as the reason for their separation.