Dean's living every writer's dream. His first book made all best-selling lists and got him a nice little house in an idyllic town, where he can focus on his writing.
Of course, it would be easier to focus if he could think of something other than the gorgeous Charlie. Just asking her out on a date would give meaning back to his life and his writing. The thing is he made a fool of himself first time they met, and hasn't stopped since.
He's going to give it one last shot. If this doesn't work, he'll accept defeat. But he's going down with a bang.