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 Rachel Dratch as Roz Pinwheel Hal Williams as Albert Meagle Questlove as LeVondrious Co Starring Rodney To as Typhoon Maxwell Weaver as Stephen Carter Weaver as Westley Kaitlyn Otey as Sonia Louisa Abernathy as Grace Callahan Krystal M. Harris as Jennifer Alanna Boatright as Michelle Greta Sesheta as Reverend Althea Nike Bob Telford as Walden Wencythe-Hoffstrike Jamison Reeves as Turk