500 Questions Main cast, played by Dan Harris Episode 2x01: Night 1 (May 26, 2016) Episode 2x02: Night 2 (May 27, 2016) Episode 2x03: Night 3 (May 28, 2016) Episode 2x04: Night 4 (May 31, 2016) Episode 2x05: Night 5 (Jun 1, 2016)