- Adam Sandler as Barry Egan, an unmarried entrepreneur with social anxiety
- Emily Watson as Lena Leonard, Barry's love interest and Elizabeth's friend and coworker
- Philip Seymour Hoffman as Dean Trumbell, the owner of the mattress store
- Mary Lynn Rajskub as Elizabeth Egan, one of Barry's seven overbearing sisters
- Luis Guzmán as Lance, Barry's coworker
- Robert Smigel as Walter, a dentist and Barry's brother-in-law
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