Guest Stars Caitlin Thompson as Madison Peter Onorati as Stanley Pearson Iantha Richardson as Adult Tess Joy Brunson as Shauna Arianna Ortiz as Dr. Sara Arroyo Hunter Parrish as Alan Sumalee Montano as Dr. Gail Jasper Mo McRae as Déjà's Father Jeremy Luke as Darryl McGee Natalie Morales as Herself Brandon Morales as Co-Worker Darryl Wesley as Déjà's Father Co Starring Makenzie Lee-Foster as Young Déjà Stephanie Ray as Liz / Group Leader Angela Fornero as Gretch Rafael Cabrera as Franco Harris Chuck Ramage as Man #1 Jill Lynne Johnson as Laurie Brianna Bryan as Teen Girl Nansi Aluka as Italian Mom Cooper Mothersbaugh as Ticket Seller Alfred Woodley as Man Denell Johnson as Vendor Tacey Adams as Judge Paige Smith as Man #2