 In March 2016, Aiko announced a collaboration album with rapper Big Sean, under the name Twenty88, their self-titled debut album was made available to stream exclusively on TIDAL for four days, and was made available for download on April 1.According to the duo, “TWENTY88 tells the story of the highs and lows of a relationship, with insights into conflict, memories, love, sex, and more and features production from Key Wane, Detail, and Tommy Brown.” From late 2016 to mid-2017, Aiko released numerous non-album singles such as "Maniac", "First Fuck" with 6lack and "Hello Ego" featuring Chris Brown.The lead single to her second studio album, "While We're Young', was released in June 2016.