Individuals with depression have difficulty anticipating pleasure, which can negatively impact motivation and functioning. One factor in this may be impairments in their episodic future thinking (EFT). This study examined whether enhancing EFT through increasing detail/vividness and mental imagery would increase anticipatory pleasure among individuals with Major Depressive Disorder. A randomized start-point, single case series design was used. Depressed outpatients (N = 7) completed surveys throughout the day over 2 wks to nominate upcoming positive events and rate them on EFT detail/vividness, mental imagery, and anticipatory pleasure. At a randomized start-point, activities to enhance the detail/vividness and mental imagery for these upcoming events were introduced. Significant increases in detail and imagery were observed when EFT activities were introduced, which correlated with increases in how pleasurable it was thought the activities would be and how pleasurable it was thinking about them. Enhancing EFT may be a mechanism to increase anticipatory pleasure in depression. Implications for treatment are discussed.