Guest Starring: Sean Maguire (Dave), Marguerite Moreau (Madelyn), Ty Jones (Isaac), Austin Pendleton (Dr. Boyd), Gloria Votsis (Holly)
Co-Starring: Joe Lo Truglio (Jimmy), Shalin Agarwal (Sketch Artist), Ranjit Chowdhry (Psychiatrist), Nick Cordileone (Photographer), Joe Farrell (Wall Street Guy), Ken LaRon (Man in Suit), Jordan Leeds (Features Editor), Dante Nero (Bouncer), Angela Pietropinto (Waitress), Kate Simses (Just Off the Bus), Dan Ziskie (Doctor), Corey Snide (14-Year-Old Boy)
Written By: Rob Thomas
Directed By: Bharat Nalluri
Ep: 2
Live and Let Spy
Guest Starring: Julie Ann Emery (Riley), Erik Palladino (Mick), Mary Stuart Masterson (Mira), John Cunningham (Grayson Davis), Chris Henry Coffey (Kevin)
Co-Starring: Melanie Nicholls-King (Celia), Mikaela Brandon (Jessie), Emilio Delgado (Gus), Denia Brache (Bibi), Kyle Dean Massey (Cory), J. Tucker Smith (Mr. Strathmore), Celeste Cruz (Teenage Girl), Candice McKoy (Anxious Young Mother), Chino Maurice (Rasta Singer), Krista Braun (Business Woman), Janelle Fletcher (Young Child #1), Nicholye Monteith (Young Child #2)
Written By: Diane Ruggiero
Directed By: John T. Kretchmer
Ep: 3
The Great Right Hope
Guest Starring: Julie Hagerty (Liv), Lee Tergesen (Clint), Anna Chlumsky (Josie), Constance Zimmer (Hallie), Colton James (Marshall), Annabelle Gurwitch (Manday)
Co-Starring: Gideon Banner (Liberal Man), Kari Swenson Riely (Conservative Woman), David Lavine (Meek Man), Jordan Haynes (16-Year-Old Boxer), Paul Urcioli (Ronnie), Greg McFadden (Jack), Susan Stewart (Skyler), John R. Trigonis (Hector), Gillian Amalia (Beatnik Sexpot), Brian McCormack (Bully's Dad), Natalie Douglas (Mother #1), Juan Luis Acevedo (Father #1), Leona Cyphers (Mother #2), Steve Greenstein (Father #2), Eric Saiet (Mr. Roberts), Angelo Massagli (Bully)
Written By: David Walpert
Directed By: Michael Grossman
Ep: 4
The Tommy Brown Affair
Guest Starring: Adam Kaufman (Tommy Brown), Shirley A. Rumierk (Paula Travato), Anna Chlumsky (Josie), Trieste Dunn (Sonja)
Co-Starring: Amy Schumer (Heather), Alexis Suarez (Benny), Faith Sandberg (Middle-Aged Woman), Craig Bockhorn (Middle-Aged Detective), Ed Wheeler (Doorman), Brian O'Neill (Supervisor), Joe Gonzalez (Uniform Cop), Beth Ellen Patrick (News Anchor), Bryan Scott Johnson (Guard)
Written By: David Walpert
Directed By: Matthew Diamond
Ep: 5
Shipping Out
Guest Starring: Patrick J. Adams (Joe), Aubrey Dollar (Robin Peachtree), Anna Chlumsky (Josie), Ptolemy Slocum (History Teacher)
Co-Starring: Blanchard Ryan (Bosomy Ellie), Julie Craig (Tracy Flick Type), Theo Stockman (DJ), Sean Andrew (Security Guard)
Co-Starring: Lucian Maisel (Adam), Tobias Campbell (Ben), Robert Harrison (Himself), Michael J. Burg (Scott Sussman), Walter R. Turney (Auggie), Kim Shaw (Pop Star, Kathy Deitch (D-Line / Clerk), Chloe Cmarada (Hot Ditzy Redhead), Spencer Fox (Music Geek), Sean-Michael Bowles (Aaron the P.A.)
Written By: Michael Oates Palmer
Directed By: Michael Grossman
Ep: 7
My Fair Masseuse
Guest Starring: Kerry Butler (Debbie), Patch Darragh (Walter Blackstock), Anna Chlumsky (Josie), Paul Fitzgerald (Lance Stillwell)
Co-Starring: Stephanie DiMaggio (Francine), Johnny Hopkins (Irish Guy), Kate Simses (Young Ingénue), Rebecca Watson (Real Francine), Joe Farrell (Wall Street Guy), Royce Johnson (Head Waiter), Sherri Norige (Waitress), Jonathan Stewart (Well-Heeled Friend), Anthony Mangano (Anthony Russo), Roger Rathburn (Mr. Stillwell), Kit Flanagan (Mrs. Stillwell)
