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All The Details Of Britney Spears & Colin Farrell's Y2K Fling

Author

Jessica Burns

Published Mar 22, 2026

In Britney Spears’ tell-all memoir, “The Woman In Me,” she recalled her short but impactful fling with Colin Farrell. The “Toxic” singer explained that she decided to move on after learning that her ex, Justin Timberlake slept with multiple women shortly after they called it quits. She chose to pursue Farrell after she saw him one time and decided he was a good-looking man. Without giving it too much thought, Spears pulled up to the set of Farrell’s movie “SWAT” after a friend told her the location. 

Spears admitted she was nervous, but the cast and crew made her feel welcome. When Farrell spotted the “Gimme More” singer sitting on the director’s chair, he asked her for ways in which he could improve his performance. Eventually, the relationship got physical, and Spears wrote, “We wound up having a two-week brawl. 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.”

Then, Farrell asked her to come to the “The Recruit” premiere where she met his family, who were very welcoming. However, Spears was wary about falling in love with Farrell because she still hadn’t processed her breakup with Timberlake. She explained, “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.”

Post source: The List