A New York schoolteacher experiences a midlife crisis when, in quick succession, her husband leaves, her adoptive mother dies, and her biological mother, an eccentric talk show host, materializes and turns her life upside down as she begins a courtship with the father of one of her students.
| Actor | Role |
|---|---|
 Helen HuntApril Epner | April Epner |
 Bette MidlerBernice Graves | Bernice Graves |
 Colin FirthFrank | Frank |
 Matthew BroderickBen Green | Ben Green |
 Ben ShenkmanDr. Freddy Epner | Dr. Freddy Epner |
 Lynn CohenTrudy Epner | Trudy Epner |
 John Benjamin HickeyAlan | Alan |
 Salman RushdieDr. Masani | Dr. Masani |
 Daisy TahanRuby | Ruby |
 Tommy NelsonJimmy Ray | Jimmy Ray |
 Stephanie YankwittStacey | Stacey |
 Lillias WhiteSheila | Sheila |
 David CallegatiGianni | Gianni |
| KKenneth SternRabbi | Rabbi |
 Robert LuPoneTed | Ted |
 Chris ChalkOrderly | Orderly |
| AAlexa Scott-FlahertyMother #2 | Mother #2 |
| MMarina DurellAttendant | Attendant |
| SSadie HestonTrudy Jr. | Trudy Jr. |
 Stephanie BerryPrincipal Petticord | Principal Petticord |
 Lauren KleinAlice | Alice |
 Cherise BootheMother #1 | Mother #1 |
| DDoug HughesBernice Fan | Bernice Fan |
| CChelsea AltmanGirl in Freddy's Bed | Girl in Freddy's Bed |
| SStacie LinardosAnne | Anne |
| JJordan ThalerJordan | Jordan |
| MMichael HarderMichael | Michael |
 Geneva CarrWoman in Her 20s | Woman in Her 20s |
 Maryann UrbanoWoman in Her 30s | Woman in Her 30s |
 Maggie SiffLily | Lily |