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2. Ian Somerhalder & Nina Dobrev

Working together on The Vampire Diaries, Ian Somerhalder and Nina Dobrev eventually turned their working relationship into a romantic partnership. But when they split, they couldn’t just throw in the towel and go their separate ways. They were still forced to work with each other. When he was promoted to being a director of the series, he was given the task of directing everyone – even his ex-girlfriend. Breaking up is hard enough. Imagine having to see your ex everyday you go to work! Thankfully, they appear to be pretty cordial years after their breakup, but will we see them starring in a sitcom together again? Probably not.

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