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It was after this rather brief relationship that Scarlet went ham on Hollywood and proceeded to date and marry all of the most eligible bachelors. Scarlett was said to have been dating none other than actor Jude Law.

We cannot blame her for being totally blind to his escapades because, back in 2003, Jude still had all of his hair and she was not the megastar she is today.

However, Jack was also Scarlett’s boyfriend when the two were in high school.

The both attended Professional Children’s School in New York. They each went their separate ways, but Jack did not let sleeping dogs lie and wrote her into one of his songs: “Fame swept her off her feet/she sees nothing she did before…

This Bobby Flay photo was taken not too long ago, so we’re sure there is more to be found out about this pair.