Patti Petalson is a promising writer, but her marriage and conventional job keep her from her dream. She longs to return to her writing, especially after running into her first love Brian Callahan, a successful crime novelist. Kate is Patti's best friend since college; she's a tough-talking schoolteacher who plays therapist to all Patti's problems, while she's got a few of her own.
Paulie (Edward Burns) sufre un ataque de miedo al compromiso justo la semana antes de casarse con su novia embarazada, Sue (Brittany Murphy). Sus relaciones con sus amigos y su familia marcarán su decisión final...