9. Sandra Bullock
Every attractive, single, and young man in Hollywood needs a fling or two with a “cougar” and JT is known for his older lady lust.
Porcelain-skinned Sandra Bullock would be a pretty companion on Justin Timberlake’s arm and her effervescent smile would go well with his cheeky swagger.
It would have to just be a brief interlude though, because unless Timberlake is willing to settle down (our guess is that he’s not), Bullock can’t afford any more heartbreak.