On his ride through 2001, Tom interacts with some of his friends, including Bran, Karen & Mike, Rollo, and Shooter (among others).

His friends include his default date, Bran, who is something of a female friend, though the relationship is undetermined; Karen & Mike, the married couple (and unlike in the TV series, Karen is not his sister); Shooter, the tall, powerful, rich, ladies man, who is black.

Brandy 'Bran' Lowenstein: Bran works as a producer for a television news program, is Jewish, and is Tom's “default” date.

Katie/Kate/Katherine: Tom's law-student girlfriend, who is increasingly talking in lawyer speak and whose personality shifts from tarot card reading Katie to extremely serious Katherine as she moves through law school.

Liesl: Another of Tom's girlfriends, Liesl, is of German descent and works for a legal organization that represents high-profile terrorist, murder/serial killer type clients (like the terrorists who bombed the parking garage at the World Trade Center).

Shooter has very strong feelings about women and never has a problem finding a woman to spend time with.

Several Bob Dylan songs, including "Idiot Wind", "If You See Her Say Hello", "Simple Twist of Fate", and "You're Gonna Make Me Lonesome When You Go", and numerous other musical works are mentioned in this book (including Train's "Drops of Jupiter (Tell Me)", and Pink Floyd's The Wall).