Guest Stars Eris Baker as Tess Pearson Faithe Herman as Annie Pearson Jon Huertas as Miguel Rivas Alexandra Breckenridge as Sophie Milana Vayntrub as Sloane Sandburg Hannah Zeile as Young Kate (15) John Pollono as Tyler Niles Fitch as Young Randall (15) Sam Trammell as Ben Logan Shroyer as Young Kevin (15) Hari Dhillon as Sanjay Jahiri Adam Bartley as Duke Katie Couric as Herself Co Starring Julia Cho as Jill Cyndi Melendez as Kelsey Krys Marshall as Stacy Karen Huie as Nurse Jenna Dar Dixon as Buchanan Ashli Dowling as Brunette Sean Bolger as Waiter Hal Perry as Salesperson Roni Geva as Mommy with Stroller