Dated: 1998-2001

Before the whole Kutcher/Demi Moore fiasco, and before he even dated the late Brittany Murphy, the former Mr. Trucker Hat was linked to January Jones, a then-budding actress who hadn't gotten her breakout role yet. Allegedly, Kutcher didn't believe Jones would have success as an actress and discouraged her from pursuing her dreams. Years after the two split, Jones landed Mad Men.