Season 5
Episodes
1 Rosie O'Donnell vs Nate Berkus and Michael Kosta vs Roy Wood Jr. May 26, 2021 2 Rachel Dratch vs Chris Redd Tonight and Dr. Oz vs Daphne Oz" Jun 2, 2021 3 Alex Moffat vs Michelle Collins and Dominique Jackson vs Indya Moore Jun 16, 2021 4 Ali Wentworth vs. Sara Haines and Kal Penn vs. Michelle Buteau Jun 23, 2021 5 Lorraine Bracco Vs Ralph Macchio And Rosie O'Donnell Vs Paige Davis Jun 30, 2021 6 Joe Gatto vs Sal Vulcano and Desi Lydic vs Nikel Welch Jul 7, 2021 7 Bridget Everett Vs Dulce Sloan And Kathy Najimy Vs Mario Cantone Jul 21, 2021 8 Ana Gasteyer Vs Rachel Dratch And Joe Gatto Vs James Murray Jul 28, 2021 9 Ryan Eggold vs Elizabeth Marvel and Joe Tessitore vs Tiki Barber Aug 11, 2021 10 Ginger Zee vs Dascha Polanco and Dorinda Medley vs Sonjia Morgan Aug 18, 2021 11 Ana Gasteyer vs Luke Kirby and Ashanti vs Clay Aiken Aug 25, 2021 12 Kal Penn vs Kathy Najimy and Neil deGrasse Tyson vs Gilbert Gottfried Sep 1, 2021 13 Mario Cantone Vs Laura Benanti And Joe Tessitore Vs Bridget Everett Sep 15, 2021