By following characters who navigate a city they do not entirely understand, this thesis examines the roles that space and place play in the evolution of identity. As twenty-first century picaros trying to take advantage of a place they feel takes advantage of them, my characters demonstrate the effects that space may have on how we view ourselves and those around us. My thesis draws primarily on the spatial theories of Timothy Cresswell, Edward Soja and Jean Baudrillard, and the picaresque studies of Ulrich Wicks and Marina Brownlee. As long as we continue to construct spaces designed to appeal to some users while excluding others, space will remain a major factor in identity construction. As the characters in my thesis prove, not everyone responds to the spaces around them with the best of intentions.