Guest Stars Sophie Zucker as Abby Kevin Yee as Toshiaki Allegra Heart as Abiah Darlene Hunt as Maggie Gus Birney as Jane Humphreys Finn Jones as Samuel Bowles Pico Alexander as Henry "Ship" Shipley Ayo Edebiri as Hattie Timothy Simons as Frederick Law Olmsted Co Starring Neville Lee as Clara Erin Gerasimovich as Anna Alexis Floyd as Proposal Friend #5 Sergio King as Proposal Friend #1 Joan Jaffe as Proposal Friend #15 Nacho Tambunting as Proposal Friend #11 Erin Kommor as Proposal Friend #7 Joseph Fierberg as Proposal Friend #13 Caroline Pluta as Proposal Friend #9 Anna Stone as Proposal Friend #2 Brianna Latrash as Proposal Friend #3 Lauren Dalal as Proposal Friend #4 Ryan Manuel Koerber as Proposal Friend #6 Tricia DeSario as Proposal Friend #8 Emma Diner as Proposal Friend #10 Trevor Hosteen McChristian as Proposal Friend #12 Tom Giron as Proposal Friend #14 Roger Preston Smith as Proposal Friend #16