7. Shia LaBeouf and Hilary Duff
Not even all of the Autobots could’ve saved Shia LaBeouf from what he dubbed as “probably the worst date either of us has ever had,” referring to the dinner he had with Hilary Duff, back when the two were dating.
8. Marilyn Manson and Evan Rachel Wood
Believe it or not, the two dated and eventually got engaged – to which Evan Rachel Wood says, “people make mistakes.”
9. Andre Agassi and Barbra Streisand
Tennis star Andre Agassi and singer / songwriter Barbra Streisand became an item back in the 1990s, to which Agassi acknowledged and wrote how “dating Barbra Streisand is like wearing Hot Lava.”
