When two people "connect" the bond between them can be so pure and simple as to stir hearts in heaven. When they connect in all the right places at all the wrong times, heaven weeps for broken hearts. To heal these broken hearts, heaven breaks time.

Davis (Jake Gyllenhaal), a successful investment banker, struggles after losing his wife in a tragic car crash. Despite pressure from his father-in-law, Phil (Chris Cooper), to pull it together, Davis continues to unravel. What starts as a complaint letter to a vending machine company turns into a series of letters revealing startling personal admissions. Davis' letters catch the attention of customer service rep, Karen (Naomi Watts), and, amidst emotional and financial burdens of her own, the...

Warren Schmidt has led a safe, predictable life working in the insurance industry in Omaha, Nebr. for many years, yet now faces retirement. At the same time he is forced to take a hard look at his wife, his life and his relationship with his estranged daughter. An often hilarious series of events follow as Schmidt embarks on an unpredictable RV journey to attend his daughter's wedding in Denver.

In the mid-1970's, a homely, friendless Australian girl of 8 picks a name out of a Manhattan phone book and writes to him; she includes a chocolate bar. She's Mary Dinkle, the only child of an alcoholic mother and a distracted father. He's Max Horowitz, living alone in New York, overweight, subject to anxiety attacks. He writes back, with chocolate. Thus begins a 20-year correspondence, interrupted by a stay in an asylum and a few misunderstandings. Mary falls in love with a neighbor, saves...