2. Gwyneth Paltrow
An oldie but a goodie. Affleck dated actress Gwyneth Paltrow from 1997 – 2000; she was the star and he was just kind of making a name for himself with his bestie Matt Damon. Paltrow recently divorced her husband of 10 years Chris Martin, so maybe she is not looking for anything too serious, but we all know the best relationships start off with the significant others being great friends before being lovers. Besides, they both had time to move on, create new relationships, experience different things and this could possibly be the optimal time to see if round two is worth it.
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