With John's social life at a standstill and his ex-wife about to get remarried, a down on his luck divorcée finally meets the woman of his dreams, only to discover she has another man in her life - her son. Before long, the two are locked in a battle of wits for the woman they both love-and it appears only one man can be left standing when it's over.
| Actor | Role |
|---|---|
 John C. ReillyJohn Kilpatrick | John Kilpatrick |
 Jonah HillCyrus Fawcett | Cyrus Fawcett |
 Marisa TomeiMolly Fawcett | Molly Fawcett |
 Catherine KeenerJamie | Jamie |
 Matt WalshTim | Tim |
 Kathy Ann WittesAshley | Ashley |
 Diane MizotaThermostat Girl | Thermostat Girl |
 Katie AseltonPretty Girl | Pretty Girl |
 Jamie DonnellyPastor | Pastor |
 Tim GuineeRoger | Roger |
 Steve ZissisRusty | Rusty |
 Bill 'Bunky' MillerCyrus | Cyrus |
 Charlie BrewerStranger at Reception | Stranger at Reception |
 Mitch CarterAdditional Voice (voice) | Additional Voice (voice) |
 Newell AlexanderAdditional Voice (voice) | Additional Voice (voice) |
 Steve AltermanAdditional Voice (voice) | Additional Voice (voice) |