One of the themes of this novel is that complete emotional distance from others is not sustainable over time. Will, the main character, originally lives in a way that distances him completely from any real interaction with others. It is fitting that his comfortable income comes from his father's silly hit Christmas song, as Will is completely absorbed in a superficial way of life. His understanding of life is that of an immature, detached person, and he joins a single parents' group only as a way to meet women. He has little appreciation of the deeper realities of what single parents' lives are like, and he only wants the veneer of being a single parent for his own limited ends.

However, Will's relationship with Marcus, the son of a single, suicidal mother, draws Will into a deeper reality, and he realizes that his interaction with others has deeper meanings and effects. His coaching of Marcus, however, involves teaching the boy to seem cool rather than involving any serious emotional interaction at first. However, over time, Marcus's newfound appreciation of music and pop culture, learned at Will's side, helps him connect with peers and form friendships with them.

Another theme of the book is the balance between surface coolness and deeper feeling. Hornby is suggesting that while Will must mature and move away from a surface, pop-culture-infused vision of life, Marcus must embrace some of pop culture and "coolness" to form closer relationships with his peers. In the end, after falling in love with Rachel, Will moves a bit closer to Marcus's more emotional way of being, while Marcus becomes more involved with his peers and becomes a bit cooler, like Will.