Gena Rowlands and Sean Connery are Hannah and Paul, a couple whose long and seemingly comfortable marriage is threatened by surprises from within and without. Gillian Anderson is Meredith, a staunchly single, passionately serious theatre director whose determination to avoid romantic complications is challenged by the funny and tenacious Trent, played by Jon Stewart. It takes a persistent suitor not to be discouraged by Meredith’s relentless expectations of doom – not to mention her 175 lb. pet Mastiff. Meanwhile, Hugh, portrayed by Dennis Quaid, is a loner, a man who hangs out at bars recounting sad stories of tragic love to total strangers under the influence. Somehow, every time Hugh opens his mouth, the circumstances of his blues become more and more imaginative.

Elsewhere, Jay Mohr is Mark, a man with a few days left to live, and Ellen Burstyn is his strong but loving mother, who must face her son on new emotional turf where honesty is the only rule. Even in this sterile setting, mother and son feverishly race the clock to relive and recreate their fragile relationship. Madeleine Stowe and Anthony Edwards are Gracie and Roger, a couple who find companionship and sexual diversion in a clandestine affair in a high-rise hotel room where reality is checked at the door. Youngest of all, Joan, played by Angelina Jolie and Keenan, portrayed by Ryan Phillippe, are two single people losing themselves in the L.A club scene, daring to hope for love in an era that has intensified the search with new obstacles.

Over the course of eight days and nights, each of these men and women will impact each other’s lives and thoughts about love in unexpected ways.