Guest Stars Craig Parker as Alastair Caine Aleyse Shannon as Jada Shields Virginia Williams as Charity Callahan Rya Kihlstedt as Dr. Julia Wagner Constantine Rousouli as Hunter Caine Anna Maria Perez de Tagle as Lainey Abraham Lim as Chip Co Starring Khamisa Wilsher as Aliya Rick Pearce as Mugger Ryan Jinn as Wes Sheila Tyson as Waitress Brad Bergeron as Adorable Guy Nathan Ozee as Shy Guy Charlie Nesbitt as Cute Date Allison Klause as Adorable Girl Amanda Voll as Woman Jennifer Rose Garcia as Aptitudematch Employee