Britney Spears is undoubtedly one of the biggest names in pop music’s history. Since her rise to stardom in the late nineties, the “Princess of Pop” has also been in quite a few high-profile relationships. While some names like Justin Timberlake and Kevin Federline stand out, the “Baby One More Time” singer has some other notable names in her dating history. She is currently single, however.
Her recently released memoir, The Woman In Me, has been taking the public down memory lane. Some topics she’s explored include the many highs and lows in her career, as well as her recently ended conservatorship and gaining back her freedom. Additionally, it also shines some light on her romantic history and the intricacies of her relationships. From the brief romances to her deepest loves, let’s take a look at the relationships Britney Spears has had since her rise to fame.
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Justin Timberlake (1998 – 2002)
The “Toxic” singer had met Justin Timberlake when they were both child stars on the set of The Mickey Mouse Club in the early nineties. Their friendship eventually blossomed into a dreamy union that lasted four years. Unfortunately, the relationship ended on a sour note in 2002 with rumors of infidelity on the part of both singers.
With the release of The Woman In Me, some previously unknown details about their time together have been revealed. For example, Britney Spears revealed that she terminated her pregnancy because the former NYSNC star “was not ready to be a father.” Understandably, Timberlake has been receiving widespread backlash since these revelations have surfaced.
Wade Robson (2002-2003)
Rumor had it that Britney Spears was hooking up with choreographer, Wade Robson, while she was dating Justin. Perhaps these rumors were fueled by the fact that she got together with him not long after her former relationship ended. Nonetheless, they did share a brief romance between 2002 and 2003. Robson and Spears were together for about a year before they called it quits in 2003.
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Colin Farrell (2003)
After things ended with Robson, Britney was linked to both Jared Leto and Fred Durst. However, Spears never admitted to dating any of these men. She did, however, admittedly date Irish actor, Colin Farrell. Moreover, she shared that they had a passionate, sexually driven fling that lasted about two weeks. The pair also were seen making out at a nightclub in L.A.
Columbus Short (2003)
Britney Spears and Columbus Short had a brief fling in 2003. Their romance was rather short-lived, especially as Short had an eight-month pregnant wife at the time. Per Hollywood Life, the affair resulted in the end of Columbus’s marriage. Previously, Columbus had been a backup dancer for Britney, but that also ended after their affair came to light. In his 2020 autobiography, Short Stories, Short revealed that Spears’ parents did not approve of their brief time together. Moreover, he claimed that they referred to him with a racial slur while on the phone to their daughter.
Jason Alexander (2004)
Britney’s shortest relationship is her marriage to Jason Alexander, which lasted only 55 hours. The wedding took place in Las Vegas, and Britney has since admitted she had been drunk and was just having fun. Jason Alexander was a childhood friend, and according to her memoir, they were not in love. The timespan of their annulled marriage quickly became a famous topic at the time.
Kevin Federline (2004-2007)
In the same year of her 55-hour long marriage, Britney fell in love and settled down with Kevin Federline. Federline had once been a backup dancer for Justin Timberlake. The marriage seemed to be going well until 2007, when Britney filed for a divorce due to irreconcilable differences. The union also produced two sons, one in 2005 and another, one year after. Their relationship was widely covered by the media. Post-divorce, Britney Spears became catnip for the paparazzi, especially as her infamous shaved-head “breakdown” occurred soon after their divorce.
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Adnan Ghalib (2007-2008)
After ending things with Kevin Federline, Britney briefly dated J.R. Rotem, a music producer. Later that year in December, she surprisingly got with photographer Adnan Ghalib, while he was married. Spears’ relationship with Ghalib also came as a shock because he was a paparazzo. At the time, cameramen and flashing lights were unwelcomingly all over Britney. The relationship was short-lived, however, and ended with Jamie Spears, Britney’s father, filing a restraining order against Ghalib.
Jason Trawick (2009-2013)
Jason Trawick was Britney’s manager at the time, and their relationship was one of her longest. The pair were also engaged, but unfortunately, it was abruptly called off after one year. At the time, the rumor mill insisted that Trawick was simply a spy for Jamie Spears, but he denied it. This rumor was further fueled by the fact that he became a co-conservator with Jamie Spears. Trawick recently received backlash for revealing on Kevin Connelly’s podcast that he believed Britney Spears needed the conservatorship at the time. He claimed Federline was spending a lot of her money and she needed someone to give her “some guidance.”
David Lucado (2013-2014)
Britney Spears met David Lucado at a party and was reportedly introduced to him by her friends. This introduction blossomed into a relationship that lasted for a few months. Unfortunately, Spears had reportedly found a video of David making out with someone else. Expectedly, this led her to call it quits.
Charlie Ebersol (2014-2015)
Britney Spears met Charlie Ebersol through her assistant not long after her split from David Lucado. The relationship lasted for only a few months, as the couple split in mid-2015. Nonetheless, the relationship succeeded in shying away from headlines while it lasted. Ever sold was notably private, while Spears had been adjusting to a more serene lifestyle.
Sam Asghari (2017-2023)
Sam Asghari was Britney’s most recent heartthrob, and their union of six years is her longest ever. Their relationship began in early 2017, but they actually met in 2016 on a music video set. Their relationship went on relatively well, with Sam supporting the pop superstar through the court proceedings that ended her 12-year-long conservatorship. The couple also got married in 2022, with high-profile guests like Drew Barrymore and Madonna in attendance. Unfortunately, they got separated in August 2023, after one year of marriage and a six-year relationship.
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