Prince William (The First Time)
While the two attended college and shortly after, Kate Middleton and Prince William eventually dated. They even shared a flat together while finishing up school. But unfortunately for Kate Middleton, the two broke it off for a brief period of time around 2007. The couple was even rumored to have broke it off over the phone. Ouch. Even if you’re royalty that’s not a good move. But why? Apparently he broke up with Kate over pressures from the royal family.