Caroline Flack – Now
Incredibly, Prince Harry isn’t the only “Harry” Caroline had been romantically involved with over the years. She briefly dated Harry Styles from One Direction. However, plenty of fans were shell-shocked once they found out the two had a 14-year age gap. At the time, Styles was only 17. In 2018, Flack started dating Andrew Brady, who recently competed in The Apprentice and also in Celebrity Big Brother. Just several months after they met, they announced their engagement.

Caroline Flack – Now
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