Special Guest Stars Kathryn Hahn as Jennifer Barkley Christie Brinkley as Gayle Gergich Guest Stars Billy Eichner as Craig Middlebrooks Natalie Morales as Lucy Susan Yeagley as Jessica Wicks Keegan-Michael Key as Joe James Michael Connor as Eugene Pilogrimaldy Ginuwine as Himself Questlove as LeVondrious Rachel Dratch as Roz Pinwheel Hal Williams as Albert Meagle Co Starring Rodney To as Typhoon Maxwell Weaver as Stephen Carter Weaver as Westley Kaitlyn Otey as Sonia Krystal M. Harris as Jennifer Alanna Boatright as Michelle Louisa Abernathy as Grace Callahan Greta Sesheta as Reverend Althea Nike Bob Telford as Walden Wencythe-Hoffstrike Jamison Reeves as Turk