The heartbroken heartbreaker
Through allegory, we learn about an archetypal man. Instead of viewing the traditional womanizer through the lens of power that such a man often projects, this book shows a womanizer who is devastated by loss. He doesn't use women because he hates women, but because he is shattered, because he suffers with intimacy issues, and because, secretly, he can't help but hold out hope that one day, the love that he lost might be restored somehow.
Comparison lists
The book uses countdown lists and music charts as a symbol for the way Rob views women in his season of dysfunction. Instead of seeing the intrinsic value of their persons, he views them through the lens of entertainment, ranking his experience with each woman for his personal experience of them. He makes women into objects by ranking them in this fashion, so that lists are a symbol for the damages of viewing other people this way. This approach leaves him chronically crippled by loneliness.
Laura as a symbol
Rob's recent ex-girlfriend, Laura, is an important part of his journey back into love. When he has his personal epiphany about his need for emotional growth and intimacy, he reaches out to her. She dumped him, so she symbolizes his self-esteem and the dilemma of adequacy, which is resolved when they work things out. In the meantime, she has moved on to an older, more established suitor, a sign for her desire for stability and respect.
The death of Laura's father
Through the death of Laura's father, Rob ends up reevaluating his opinion of romance. Instead of seeing a mate as an object to be attained and possessed, he considers what it means to participate in a family. He sees the value of a different kind of love, and he mourns the father in a meaningful way, considering whether this father could ever have been a true family member to Rob. The death symbolizes his need for family love and fidelity.
The mix tape
A mix tape is like a playlist, but back before people could just listen to anything anytime. The gift was meaningful, because (typically) the person would have to wait for the song to come on the radio to record it, so it took a great deal of time, and in Rob's case, the songs are designed to signify his feelings for Laura and his commitment to growth. This is the gift of a soundtrack for their romance, and because of Rob's attachment to music and lists, it is also a symbol for his gift of self. He is offering his own self to her.
