This chapter shows that boredom and intoxication, explored in terms of the temporality of mooded experience, are deeply interrelated. In the homeless context, boredom is the primary filter through which the homeless experience and make sense of time, and by extension the truncated nature of their social reality. Larry’s sense of stuckness should not be understood as an internal or cognitive process, but rather as a mood that discloses his attunement to his situated place in the world—what Martin Heidegger calls ‘disposedness’. Larry’s long-standing entanglement with drugs, both economically and experientially, have built for him a prison that goes beyond the spatial and temporal dimensions of his original penal term, encompassing not just his past but also his future. Rather than operating as anything revelatory, the existential boredom experienced by Itchy Park’s homeless addicts serves instead to affirm their nothingness.