It has recently been argued that hope is polysemous in that it sometimes refers to hoping and other times to being hopeful. That it has these two distinct senses is reflected in the observation that a person can hope for an outcome without being hopeful that it will occur. Below, I offer a new argument for this distinction. My strategy is to show that accepting this distinction yields a rich account of two distinct ways in which hope can be lost, ways that map onto the two senses of hope: A person can lose hope either by ceasing to hope for an outcome (hopelessness) or by ceasing to be hopeful that it will obtain (despair). Thinking about these negative attitudes in these two ways, I contend, is explanatorily rich and fruitfully reveals how they differ in phenomenology, behavioral differences, and the ways in which a person can escape them.