Kissing Jessica Stein Cast and Crew
 Jennifer Westfeldt - (Jessica Stein) |
 Heather Juergensen - (Helen Cooper) |
 Scott Cohen - (Josh Myers) |
 Tovah Feldshuh - (Judy Stein) |
| Jackie Hoffman - (Joan) |
| Thomas Bolster - (Cheesy Pick-Up Guy) |
| Jim J. Bullock - (Not-Yet-Out Gay Guy) |
| Tibor Feldman - (Roland) |
| Allen Fitzpatrick - (Matthew) |
| Vinny Vella - (Cab Driver) |
| Ben Weber - (Larry) |
| Julie Lauren - (Josh's Date) |
| Michael Showalter - (Stephen) |
 Kevin Sussman - (Calculator Guy) |
| Ilana Levine - (Helen's New Girlfriend) |
 Jon Hamm - (Charles) |
| John Cariani - (Chuck) |
| David Aaron Baker - (Dan Stein) |
 Idina Menzel - (Bridesmaid) |
 Michael Ealy - (Greg) |
| Robert Ari - (Sidney Stein) |
| Nick Corley - (Howard) |
| Michael Mastro - (Martin) |
 Alysia Reiner - (Schuller Gallery Artist) |
| Jennifer Carta - (Rachek, Dan's Fiancée) |
| Brian Stepanek - (Peter) |
| Carson Elrod - (Sebastian) |
| Esther Wurmfeld - (Grandma Esther) |
| Hillel Friedman - (Rabbi) |
 Ben Feldman - (Ben Feldman) |
| Christopher Berger - (Malaprops Guy) |
| Hayden Adams - (Weird Smooth Guy) |
| Naomi Sablan - (Seductive Woman At Gallery) |
| Jimmy Palumbo - (Cheesy Pick-Up Guy) |
| Peter Hirsch - (Stanley) |
| Adele Reichman - (Grandma Interrogating Helen) |
| Amy Wilson - (Bookstore Saleswoman) |
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