Sparks fly when Abigail (Christina Ricci), a self-sufficient single mom, meets Benjamin (Hamish Linklater), a magnetic perennial bachelor. They bond over their shared cynicism about love, convinced that the most dazzling relationships are destined to end in disaster. On their first date, they collaborate--in jest--on the ultimate un-bucket list: ten things to do together before they break up. But when fate intervenes, this pair of cynics must embark on the most challenging journey of all, building a family together, and the chance to trade their cynicism for hope.