| Mike Andrews | ... | Tom Gomez | |
| Eliza Coyle | ... | Courtney Baker | |
| Adam Eastwood | ... | Andrew Baker | |
| John Ennis | ... | Gil | |
| Mark Fite | ... | Gus | |
| Ana Gasteyer | ... | Rosemary Colletti | |
| Kathy Griffin | ... | Ona Miller | |
| Ian Gomez | ... | Hank | |
| Dana Gould | ... | Nick Hastings | |
| Chris Hardwick | ... | Tim | |
| Sean Masterson | ... | Al Kennedy | |
| Anne Mattingley | ... | Mrs. Baker | |
| Doug McKeon | ... | Barney Cosgrove | |
| Ted Michaels | ... | Lance | |
| Taylor Negron | ... | Dr. Scott Phelps | |
| Melissa Nickert | ... | Jill Baker | |
| Philip Pavel | ... | Waiter | |
| John Rogers | ... | Aaron | |
| Nestor Ruiz | ... | Juan | |
| Al Schuermann | ... | Mr. Baker | |
| Ryan Stiles | ... | Chad Gross | |
| Sarah Taylor | ... | Karen Mulligan | |
| Michael Pitts | ... | Courtney's Class Member | |
| Brandie Tinin | ... | Courtney's Class Member | |
| Peter Wiest | ... | Courtney's Class Member | |
| Derita Sharp | ... | Party Guest | |
| Keymia Sharp | ... | Party Guest | |
| Khameelah Sharp | ... | Party Guest | |
| George Hill | ... | Video Date | |
| Paul Tarantino | ... | Video Date | |
| Hamilton Holt | ... | Video Date | |
| Joseph Alfieri | ... | Video Date | |
| Stephanie Grodell | ... | Group Therapy Member | |
| Julia Sweeney | ... | Group Therapy Member | |
| Dawn DeNoon | ... | Group Therapy Member | |
| Lance August | ... | Group Therapy Member (Wally) | |
| Sara Noonan | ... | Rita | |
| Mark Meyer | ... | Flower Delivery Man | |
| rest of cast listed alphabetically: | |||
| Nick Benedict | ... | Mr. Sinise | |
| Joseph Lawson | ... | Video Date (uncredited) | |
| Jane Morris | ... | Ms. Opremchek (uncredited) | |
Directed by | |||
| Paul Tarantino | |||
Writing credits(in alphabetical order) | ||
| Paul Tarantino | ||
Produced by | |||
| Jesse Dizon | .... | executive producer | |
| Hadeel Reda | .... | producer | |
| Serge Rodnunsky | .... | producer | |
| Chiqui Schatz | .... | executive producer | |
| Paul Tarantino | .... | producer | |
Original Music by | |||
| Daniel Gold | |||
Cinematography by | |||
| William McDonald | |||
| Tom Oetzel | |||
| Serge Rodnunsky | |||
| Lawrence Sher | |||
Film Editing by | |||
| Agita Fanucci | |||
Casting by | |||
| Stacey Pianko | |||
Art Direction by | |||
| Ellen Guthrie | |||
Second Unit Director or Assistant Director | |||
| Philippe Kardinaal | .... | assistant director | |
| Mark Meyers | .... | assistant director | |
Sound Department | |||
| Bart Carpenter | .... | sound | |
| Robert Fisher | .... | sound re-recording mixer | |
| Erich Hoeber | .... | sound | |
| Donna Metz | .... | sound | |
Camera and Electrical Department | |||
| Tolly Glickman | .... | still photographer | |
Thanks | |||
| Stu Easterday | .... | special thanks | |
| Rodney Henson | .... | special thanks | |
| James Hynes | .... | special thanks | |
| Max Kleven | .... | special thanks | |
| Benjamin John Parrillo | .... | special thanks | |
| Chris Stasi | .... | special thanks | |
| Jennifer Tarantino | .... | special thanks | |
| Rina Tarantino | .... | special thanks | |
| Trix Worrell | .... | special thanks | |
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| Never Among Friends | Notes on a Scandal | Beautiful Girls | Mean Girls | Broken Flowers |
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| Full cast and crew | Company credits | External reviews |
| IMDb Comedy section | IMDb USA section |
Nick (Dana Gould) announces to the viewer that he's about to make a documentary of the love life of his best friend, Courtney (Eliza Coyle). She is a single woman living in the Los Angeles area and she's about to turn thirty (ugh!) As the supposed documentary begins, Courtney is just ending an on-again, off-again relationship with her live-in boyfriend. The search for true love continues. Nick follows Courtney's next ventures as she tries video dating and becomes part of a therapy group for singles. No romance blooms from these attempts; they are profound failures. Will Courtney find her way to an engagement ring?
This sweet pseudo-documentary is clever and diverting. Nick is an acute observer and gives a humorous, running commentary on Courtney and her exploits. Courtney, too, is attractive and likeable; one hopes she will be able to meet her match. Adding much to the overall enjoyment of the film is the therapy group; they spout comments that are quite funny. The end of the film may be easy to guess but it is satisfying nonetheless. Although the film 20 Dates may be a slightly better realized film in the same category, Courting Courtney will appeal to the romantic in all of us. Recommended for an evening's worth of smiles and sighs.