Guest Stars Megan Ferguson as Wendy Fineman-Walsh Luke Kirby as Davis Calloway John Benjamin Hickey as Roy Sachs Lyne Renée as Helena Bergmann Malcolm McDowell as Roger Menzies Carla Hall as Rocky Hettienne Park as Jodi Menzies Elisabeth Waterston as Lara Co Starring Gigi Stone Woods as Themselves Jason Liebman as Dr. Gibson Claudia Maree Mailer as Goop Rep Shari Abdul as Maya Ayumi Patterson as Marjorie Constance Zaytoun as Revlon Rep Hannah Seusy as Nurse Zach Altman as Restaurant Host Diane Dehn as Ulta Rep Eddie Carroll as Glossier Rep