Lloyd Dobler from “Say Anything” – Secure
Despite the fact that high schoolers Lloyd Dobler and Diane Court come from different sides of the tracks and that Court is more focused on going off to college in England than getting romantically involved, the confident Dobler isn’t dissuaded.
He’s supportive of and patient with Court and doesn’t come unglued when his love keeps him at arm’s length. Instead, he shows up at her house, lifts his boombox above his head and blasts Peter Gabriel’s “In Your Eyes” to win her over—and eventually succeeds. When Court says to him, “Nobody thinks this will work, do they?” Dobler responds: “No. You just described every great success story.”