HomeCelebrityBritney Spears Dating History: How Many Men Has The Pop Star Dated?

    Britney Spears Dating History: How Many Men Has The Pop Star Dated?

    There is no denying that the ‘Oops!…I Did It Again‘ star Britney Spears has a long list of hearts tucked up her sleeves. The iconic American pop star dated 13 popular celebrities before marrying her long-time partner Sam Asghari in an intimate wedding in Los Angeles on June 9, 2022.

    Over the years Britney has aroused great media and fan interest both due to her professional as well as her personal life endeavors. Spears achieved enormous popularity for being one of the leading pop singers of the 90s. Some of her most popular albums are, ‘Baby One More Time’, ‘Oops! I Did It Again’, and ‘Circus’. Keeping her career aside, let’s check out her dating history.

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    Reg Jones (1995-1997)

    Reg Jones was Britney’s first love and according to Us Weekly, they started dating when she was just 14, and not even famous. Apparently, she also lost her virginity to Reg. The duo dated for two years and then broke up.

    Justin Timberlake (1998-2002)

    Britney’s match made in heaven was with Justin Timberlake. She met Justin when she was just 11 years old and the two were shooting for Mickey Mouse Club in the year 1992. They were one of the famous couples that made pop culture history by appearing in matching denim outfits on the red carpets. They broke up on a not-so-very-good note after four years of dating.

    Wade Robson (2001- 2002)

    According to reports, after Spears split from Timberlake, she hooked up with her dance choreographer Wade Robson. They grew close to each other when Wade co-directed Britney during her tour. The pair ended up dating for about a year and then called it quits.

    Fred Durst (2003)

    Although Spears never admitted that she had a relationship with Limp Bizkit frontman Fred Durst, she did have a short fling with him. “It just became a fiasco of madness,” Durst told MTV of their split. Their fling lasted no more than four months.

    Jered Leto (2003)

    There were rumors that ‘Toxic‘ singer Britney was also in a relationship with Jared Leto who happens to be an American actor. It is said that they met at a posh LA restaurant in 2003. They only dated for a while.

    Colin Farrell (2003)

    Britney made a red carpet appearance at the premiere of the film ‘The Recruit‘ with its handsome Irish actor, Colin Farrell. They were later spotted kissing on the balcony of his hotel room. But Farrell denied the relationship by saying, Just a 26-year-old guy who’s single and having a good time.”

    Columbus Short (2003)

    After some time of the Colin Farrell sparks, Spears was photographed locking lips with one of her backup dancers, Columbus Short. He soon confessed about his little fling with her which led to the end of both his marriage and his job.

    Jason Alexander (2004)

    Spears’ first marriage was rather short-lived. The pop star married childhood friend Jason Allen Alexander in March 2004. They got married in a chapel in Las Vegas, Nevada after a long night of partying. The wedding didn’t work out and they decided to get it annulled just after 55 hours.  

    Kevin Federline (2004-2007)

    At the age of just 22, Britney Spears fell in love and married backup dancer Kevin Federline and had two sons with him — Jayden James in 2006 and Sean Preston Federline in 2005. Britney met Kevin in April 2004 and after dating for three months, they tied the know. She filed for divorce from Federline in November 2006 stating family problems.

    J.R. Rotem (2007)

    The ‘Me Against The Music’ singer did not wait for a long time after her divorce from Kevin. In 2007 she was rumored to be in a relationship with J.R. Rotem, a music producer. Later, Rotem also confirmed their relationship. The couple didn’t stay together for long and the reason for their split is still unknown.

    Jason Trawick (2010-2012)

    After a lot of rumored flings, Jason was the one Britney came into a stable relationship with. They dated for a few years and got engaged in 2010. They also walked in together at the Grammy Awards night in 2012 but separated soon after.

    David Lucado (2013-2014)

    After her split from Trawick, Spears was spotted with a lawyer, David Lucado. They dated from 2013-2014. Britney even confirmed the breakup by writing, “Ahhhh the single life” on Twitter.

    Charlie Ebersol (2014-2015)

    In October 2014 Britney started dating a producer and the son of ‘Saturday Night Live‘ co-creator Dick Ebersol. They broke up in 2015. He confessed that he was in it “for the wrong reasons.”

    Sam Asghari (2017)

    Spears & Sam at an event
    Britney Spears and Sam Asghari at an event

    Britney Spears then finally met the ‘love of her life’ Sam Asghari in 2016 and they soon fell head over heels in love. They are currently married now.

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