In June 1997, Brad Pitt and Gwyneth Paltrow endured a very messy and very public split, calling off their engagement after two and a half years together.
Despite hinting she was the one who ended things, Gwyneth, then only 24, was so distraught that she refused to work and later admitted she was heartbroken for five long years. "I was very upset for a long, long time," she told Diane Sawyer in 2006, but insisted she eventually managed to work past it. "We're able to sort of see each other and smile and wish each other well," she added.
And according to pals, her pain was only made worse when Brad was set up with Jennifer Aniston on a blind date in early 1998 - a meeting that would result in an engagement just five months later.