Amanda Peet, “A Lot Like Love” (2005)
Kutcher often plays opposite demure and sweet starlets, but Peet might be one of the few female leads to match his permanent state of aloofness. “A Lot Like Love” begins seven years in the past, with Emily (Peet) and Oliver (Kutcher) meeting on a cross-country flight. They hook up, find themselves intrigued, but decide to prioritize their careers over settling down. As Oliver launches an online diaper company and Emily grows into a successful photographer, they reunite awkwardly along the way; one always settled while the other seems lost and adrift. What sets Peet apart in the Kutcher canon is that she’s every bit his equal, leading a successful life all her own. She plays hard to get, and he seems to like it.