1. 1998-2002: Justin Timberlake
image source: peoplemagazine.com
Britney’s relationship with pop star Justin has to be one of her most famous relationships – who remembers the twinning denim? – after the pair met during Mickey Mouse Club. There were rumours the pair split after Britney had cheated on Justin, but it was never confirmed, and he later made an official apology after the public scrutiny Britney had been subjected to.
2. 2001-2002: Wade Robson
image source: usweekly.com
In the music video for Britney’s song “(You Drive Me) Crazy”, Wade Robson was one of the dancers and choreographers, and rumours began that the pair had started dating not long after Britney had broken up with Justin. Neither Spears nor Robson ever officially confirmed it.
3. 2003: Colin Farrell
image source: glamour.com
A simple hand-hold at a movie premiere was enough to spark media speculation that Britney and actor Colin Farrell were dating, but Farrell tried to set the record straight during an interview when he explained that Britney is “just a mate” and they’d only met a week before! What do you think?
4. 2004: Jason Alexander
image source: instyle.com
Britney made it official with Jason Alexander when the pair tied the knot in Las Vegas, but it wasn’t to be – after only 55 hours the pair annulled the marriage. Hey, that’s a Vegas wedding for you! Unfortunately, Alexander couldn’t let it lie, as in later years, he would be arrested for trespassing, battery and trying to crash Britney’s future wedding.
5. 2004-2007: Kevin Federline
image source: businessinsider.com
Dancer Kevin and Britney married after only three months of dating, and they went on to have two children together. Everything seemed peachy up until 2006, when Britney filed for divorce, claiming “irreconcilable differences”. They seemed to be on good terms – until Kevin began demanding more money in child support payments…
6. 2007-2008: Adnan Ghalib
image source: okmagazine.com
In perhaps an enemies to lovers tale, Ghalib was actually a paparazzi following the singer around until the pair struck up a romance. They were together for a year, and when speaking about the relationship, Ghalib said it was more he was made out to be the bad guy by fans and the world. In the end, he had to have a restraining order against him.
7. 2009-2013: Jason Trawick
image source: pagesix.com
Trawick, an agent in Hollywood, became engaged to Britney in 2011 after they’d been dating since 2009 – but they split before they could make it to the altar. The pair both issued statements after the split saying they still wished each other the best and were still “great friends”.
8. 2013-2014: David Lucado
image source: etonline.com
It was only two months after ending her engagement that Britney began dating David Lucado, a legal firm worker – but it wasn’t to be either. After their split was announced, rumours began that Lucado had cheated on her, but he claimed that he’d been seeing another woman after he and Britney had officially broken up.
9. 2014-2015: Charlie Ebersol
image source: eonline.com
Co-founder of Tempus Ex Machina and The Company began dating Britney in 2014, and they actually managed to keep their relationship on the down low without too much drama. After they split, Britney spoke highly of him, saying he made her feel “at ease” and – bonus – he was “really hot”.
10. 2016-2023: Sam Asghari
image source: bbc.co.uk
Britney’s latest love interest has been fitness instructor Sam Asghari, who was cast in her music video for “Slumber Party”. The pair tragically lost a baby before they had their wedding ceremony in 2022, and later Asghari had to deny rumors they were going to get divorced – until it turns out the rumors were correct, and he filed for divorce after 6 years together due to – you guessed it – “irreconcilable differences”. So what’s next for Britney’s love life?
