She's not really his girlfriend. He's not really her boyfriend. She says she doesn't like him like that and he says he thinks of her as his little sister, but smarter. But she still sometimes tells others he's her "boyfriend" and he tells his classmates that she's his "girlfriend."

He shaves once a week on Sunday. If he doesn't shave he gets the slightest hint of a moustache. She doesn't like it. He talks to her on the payphone in the hallway of Hotchkiss. The hall isn't conducive to private conversations, but sometimes he wants to be overheard. He tells the older classmates that he's going to visit his girlfriend in New York City. This gives him a reprieve from the bullying. His lacrosse jersey was ruined when the older students urinated in his locker.

He grew up in a broken home. He likely spent more time with his mom and other adults than kids his own age. He probably spent a lot of time alone. There is an uncanny economy is his ability to verbally distill emotions. He is remarkably observant and is keenly aware of the sadness in others. He can be a little creepy.

He faces problems that many kids his age face. He is responsible and reckless. When asked what he would do if he could do anything, he replied that he'd like to drive a car.

For a child, is there anything more grown up than being able to drive a car?

When we were first introduced to 9-year old Glen Bishop in season one of Mad Men he was the soft spoken, sad, and insightful little boy who wanted a lock of Betty Draper's blond hair.

Season five has just ended and Glen has grown up, but the prep school deviant is really still that sad little boy in mittens.

Despite only having seen him reading one book and despite it being for a school report, I'd like to think he was a voracious reader. Sally probably also recommended books for him to read, such as The Black Cauldron and The Twenty-One Balloons.

What books do you think Glen Bishop would read? Are there books he read when he was home alone and his mom was out taking long walks? Are there books he'd read to impress older classmates? Are there books he'd read in secrecy for fear of taunts and bullying? When season one of Mad Men starts it is March 1960. It is March 1967 when season five ends. That is seven years to work with but don't let that limit you. I've selected two titles from each of those years that I feel fit right in with Glen Bishop's character and personality. I'm hoping you'll do the same. What books do you think would be on Glen Bishop's Reading List?

1960 Island of the Blue Dolphins | Scott O'Dell
         The Mystery of the Chinese Junk | Franklin Dixon

1961 James and the Giant Peach | Roald Dahl
         The Phantom Tollbooth | Norton Juster

1962 A Wrinkle in Time | Madeleine L'Engle
         Something Wicked This Way Comes | Ray Bradbury 

1963 Where the Wild Things Are | Maurice Sendak
         Dolphin Island | Arthur C. Clarke

1964 Charlie and the Chocolate Factory | Roald Dahl
         The Giving Tree | Shel Silverstein

1965 The Outsiders | S. E. Hinton
         The Black Cauldron | Llyod Alexander

1966  I, Juan de Pareja | Elizabeth Borton de Trevino
          The Castle of Llyr | Lloyd Alexander

1967  The Secret Agent on Flight 101 | Franklin Dixon
          The Black Pearl | Scott O'Dell