Guest Starring: Connie Britton (Madeleine), Laura Pallas (), Paul Adelstein (Mike), Ellie Harvie (), Jeff Parise (Nick), George Newbern (Dave)
Featuring: Tony Nappo (Hector), Charles Siegel (Dr. Greely), Sarah Strange (Pierced Nose), Christine Willes (Doctor #1), Doug Abrahams (Phil), Benz Antoine (Psychiatrist), Tim Dixon (Doctor #2), William Goodlet (Pretzel Man), Cameron Kirkwood (Horndog), Ty Olsson (Jerk), Lara Phillips (Laurie), Steve Soucy (Guitar Player), Haig Sutherland (Timothy), Ken Tremblett (Charlie Ramsey)
Co-Starring: Elisa Taylor (Monique), Paul Adelstein (Mike), Jeff Parise (Nick), Tria Smith (Sherri), Daniel Bryant (Laurence)
Featuring: Robert Bundy (Hunter), Ilyssa Fraden (Sarah), Brian Stepanek (Kevin), Heather Prete (Co-Ed Hottie), James Whiting (Sugar Blue), James Deuter (Dean Wetland), Rengin Altay (Janet), Mary Kay Cook (Prostitute)
Written By: Rob Thomas
Directed By: Scott Winant
Ep: 3
Heaven, He's in Heaven
Guest Starring: Harry Groener (), Joan McMurtrey (), David Johansen (), Hollis Resnik (), Byrne Piven (Dr. Stroud)
Co-Starring: Jeff Parise (Nick), Daniel Bryant (Laurence), Noelle Bou-Sliman (Tina), Melanie Moore (Jaclyn)
Written By: Jeff Reno & Ron Osborn
Directed By: Michael Engler
Ep: 4
A Truly Fractured Fairy Tale
Guest Starring: Robert Mailhouse (), Kate Hodge (), David Johansen ()
Co-Starring: Jeff Parise (Nick), Daniel Bryant (Laurence), Paul Adelstein (Mike), Noelle Bou-Sliman (Tina), Melanie Moore (Jaclyn)
Featuring: Tim Gregory (Nicholas), Oksana Feduntszyn (Brianna), Nambi E. Kelley (Joy), Chris Erwin (Paper Boy)
Written By: Elle Triedman
Directed By: Elodie Keene
Ep: 5
First Loves
Guest Starring: Lisa Loeb (Sophie), Hollis Resnik (), Marc Vann (Brian)
Co-Starring: Jeff Parise (Nick), Paul Adelstein (Mike), Daniel Bryant (Laurence), Noelle Bou-Sliman (Tina)
Featuring: Wayne Brown (Dr. Greeley), Olivia Miller (Young Sophie), Kevin Michael Doyle (Sophie's Father), Kathryn Jaeck (Sophie's Mother), Sean Bradley (Lister), Brett Ryback (Paul), Jeff DeRango (Young Brian), Sheila Carrasco (Young Claire), Ryan Marek (Mark), Will Malnatti (Football Kid), Barrie Buckner (Young Champ), Tatsha Davis (Jackie), David Lively (Urban Cowboy)
Written By: Hart Hanson
Directed By: Patrick Norris
Ep: 6
Meat Market
Guest Starring: Joe Flanigan (Alex), Kate Walsh (), Jennifer McComb (), Jeff Parise (Nick), Paul Adelstein (Mike), Daniel Bryant (Laurence), Anna Chlumsky (Jill)
Featuring: Noelle Bou-Sliman (Tina), Liza Cruzat (Naomi), Margaret Travolta (Congressman's Wife), Michael Guido (Congressman), Lusia Strus (Slinky Woman), Kirk Anderson (Pimp), Ian Vogt (Payphone Guy), Ed Bevan (Handsome Guy)
Written By: Rob Thomas
Directed By: Michael Fields
Ep: 7
Pick Up Schticks
Special Guest Star: Todd Field (Sam)
Guest Starring: Joe Flanigan (Alex), Sherilyn Fenn (Helen Davis)
Co-Starring: Jeff Parise (Nick), Paul Adelstein (Mike), Daniel Bryant (Laurence), Noelle Bou-Sliman (Tina)
Featuring: Pat Caldwell (Alice), Geryll Robinson (Chris), Christian Stolte (Elvis), Ed Kross (Kirk), Daniel Ruben (Ignatius), Bob Rusch (Male Jogger)
Written By: Michael Conathan & Rob Thomas
Directed By: Tucker Gates
Ep: 8
Heart of the Matter
Guest Starring: Joe Flanigan (Alex), Katy Selverstone (Susan), Matt Roth (Dan Waters)
Featuring: Melanie Moore (Jaclyn), Guy Barile (Doctor), Darren Bochat (Video Employee), Tobiasz Daszkiewicz (Jock), Linda Perlin (First Woman)
Written By: Karen Hall
Directed By: Michael Engler
Ep: 9
The End of an Eros
Guest Starring: Joe Flanigan (Alex), Garrison Hershberger (Gabe), Jennifer Crystal (Dr. Darcy Wyatt), Deborah Puette (Cutie Bowler), Wendy Whiteside (Robin), Heidi Kettenring (Chatty Cathy), Turk Muller (Sean), Amy Farrington (Stroller), Eric Johnson (Group Member)
Co-Starring:
Written By: Michael Green
Directed By: Peter O'Fallon
Ep: 10
Hung Jury
Guest Starring: Kim Fields (), Shawn Michael Howard (), Brian Baker (), Mike Nussbaum (), Matt DeCaro (Bailiff), B.J. Jones (Cal), Joey Hansa (Shelly), Julio Godinez (Lou), Steven Fristoe (Frederav Naja), Geryll Robinson (Chris)
Co-Starring:
Story By: Hart Hanson & Rob Thomas
Teleplay By: Michael Green & Michael Conathan
Directed By: David Petraraca
Ep: 11
A Great Personality
Guest Starring: Christine Taylor (Yvonne), Marc Vann (), Grant Heslov (Ken)
Co-Starring: Paul Adelstein (Mike), Jeff Parise (Nick), Daniel Bryant (Laurence), Noelle Bou-Sliman (Tina), Melanie Deanne Moore (Jaclyn), Geryll Robinson (Chris)
Featuring: Tim Decker (Gene), Joe Petcka (Lance), Laurie Fortier (Model), Hanna Dworkin (Annette), Jodi Wright (Older Woman), Owen Smith (Waiter)
Written By: Rob Thomas
Directed By: Deran Sarafian
Ep: 12
Grand Delusions
Guest Starring: Patrick Fabian (Don Quixote), Daphne Ashbrook (Mona)
Special Appearance By: Barry Newman (Bill Allen)
Featuring: Melanie Deanne Moore (Jaclyn), Tony Fitzpatrick (Mona's Boss), Sephus Booker (Mr. Clef), Tom Lowell (Jerk), Mike Vieau (Nurse)
Written By: Sy Dukane & Denise Moss
Directed By: Nick Marck
Ep: 13
Bachelorette Party
Guest Starring: Jessica Tuck (), Kelly Miller (), Scott Atkinson (Ben), Karin Anglin (), Mindy Hester ()
Featuring: Wendy Carter (Geena), Denise Odom (Heidi), Julie Greenberg (Suzanne)
Written By: Dahlia Borthwick
Directed By: Stephen Cragg
Ep: 14
The Children's Hour
Special Guest Star: Tiffani-Amber Thiessen (Stephanie MacGregor)
Guest Starring: Ben Bode (), Jamie Renee Smith (), Joey Zimmerman (), Noelle Bou-Sliman (Tina), Melanie Deanne Moore (Jaclyn), Stephnie Weir ()
Co-Starring: Paul Adelstein (Mike), Jeff Parise (Nick), Daniel Bryant (Laurence)
Featuring: Mary Ann Thebus (Ellen Calder), Lucina Paquet (Little Old Lady), Joe Foust (Goateed Clerk), Aaron Himelstein (Andy Tucker), Jacob Miller (Jesse), Joe Forbrich (Tina's Guy)
Written By: Hart Hanson
Directed By: Michael Katleman
Ep: 15
Botched Makeover
Guest Starring: Laura Leighton (Kristy Holbrook), Lance Baker (), Billie Worley (), Dan Gauthier (Tom), Stephnie Weir (Priscilla), Rebekah Louise Smith (Veronica), Tami Sagher (Velma), Gillain Vigman (Daphne), Sam Derence (Sunset), Tab Baker (Vaughn), Jill Kraft (Kim), Doug James (Roger), Paul Adelstein (Mike), Daniel Bryant (Laurence)