| Cast overview, first billed only: | |||
| Philip Seymour Hoffman | ... | Jack | |
| John Ortiz | ... | Clyde | |
| Richard Petrocelli | ... | Uncle Frank | |
| Tom McCarthy | ... | Dr. Bob Thomas | |
| Amy Ryan | ... | Connie | |
| Daphne Rubin-Vega | ... | Lucy | |
| Lola Glaudini | ... | Italian Woman | |
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Rafael Osorio | ... | Ungainly Swimmer (as Ralph Osorio) |
| Stephen Adly Guirgis | ... | MTA Worker | |
| Mason Pettit | ... | Drunk Man on Subway | |
| Trevor Long | ... | Waldorf Doorman | |
| Stephen Mailer | ... | Happy Husband | |
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Elizabeth Rainer | ... | Happy Wife |
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Theodore Mailer | ... | Young Son |
| Count Stovall | ... | Men's Room Attendant | |
Jack is a shy and awkward man who drives a limo and lives an unassuming life. His friend and co-worker, Clyde, and his wife Lucy, feel sorry for Jack and set him up on a blind date with Connie. Connie shares Jack's shyness and awkwardness, but through each other they seem to be able to find solace within themselves. Trouble might be brewing in paradise though, as Clyde and Lucy's marriage stumbles just as Jack and Connie's relationship grows. Written by napierslogs
After being set up on a blind date by his friends, Jack (Hoffman) promises to take Connie (Ryan) boating. Jack then begins to do everything he can to prove how much he like Connie. There are movies that come out that are 99% special effects and 1% acting, some are good but no matter who plays the parts it doesn't affect the movie. This one is the opposite. The story itself is one that has been done 1,000 times. A married couple sets up two awkward people and they start to fall in love while the original couple is splitting up. I know we've all seen that over and over, but the acting in this one makes it seem fresh and new. The story itself is very slow moving and basic, but the acting of all 4 main actors are what keeps you watching the movie. This is the definition of a character driven movie, the acting in the scene where Jack burns dinner is worth watching the movie for by itself. The movie is probably a C- but when the acting is taken into account it raises the level of the film. I say B-.