Literary Matchmaking: Characters Who Would Date in Real Life

Holden Caulfield and Esther Greenwood

If he could ever fall for anyone, the quintessential example of masculine teen angst would probably go for the classic example of feminine teen depression. After all, Esther’s condition is much like Holden’s, although, ahem, way less phony. The two of them could sit by the duck pond together, complaining about the oppressiveness of the world and their parents’ inabilities to fully understand them, and then maybe hold hands a little.