Gwyneth's heart may have been broken after the breakup with Brad, but she didn't stay single for long. In December 1997, the actress moved on to Ben Affleck. Learning a lesson from her previous mistakes, Gwyneth made a pointed effort to keep her relationship with Ben out of the spotlight. Still, the duo were spotted making out at a press junket for Gwyneth's film "Sliding Doors." They broke up a year later, reconciled briefly in 2000 after co-starring in "Bounce," and then split again shortly after.