Guest Stars DeRon Horton as Ray Powell Lou Taylor Pucci as Jonas Shevoore Leslie Jordan as Courtney Sean Liang as Pete Dylan McDermott as Bruce Lily Rabe as Lavinia Richter Tara Karsian as Chef Bertie Finn Wittrock as Bobby Richter Co Starring Emma Meisel as Midge Kat Solko as Helen Conor Donnally as Eddie Renton Pexa as Keith Andrew Tippie as Larry Filip Alexander as Young Bobby Briana Lane as Jess Remy Ortiz as Uber Driver Andy Greene as Passenger Riley Schmidt as Orderly