Colin Farrell & Britney Spears – 2003

Colin Farrell never got to call Britney Spears his girlfriend, but the two still went on a date together. It reportedly happened in 2003, and it seems like they had fun. Unfortunately, their connection wasn’t strong enough for them to pick up their phones and arrange a second date.

Farrell later had a short marriage with actress Amelia Warner, while Spears has two ex-husbands already. Since 2016, she has been in a relationship with Sam Asghari. She has recently been making headlines due to her conservatorship battle. Her father, Jamie, reportedly agreed to step down from it in August 2021.

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