In 2018, Berman and Cassie separated; him living in a room above Drag City’s Chicago offices. According to Berman, they "never had the kind of conflict that results in divorce" but had the "kind of need to live lives without the other one". They still had the same bank account and owned a house together; Berman considered her his family, "all [he had". At certain points in the year, he lived in Miller Beach and an alley. At one point he had requested that a friend give him heroin. He was refused—ultimately, grateful.