Late one night a woman drives by a stranded motorist who is later revealed to have been murdered. After a series of terrifying events the woman believes she is the killer's next victim.
Tom, greeting-card writer and hopeless romantic, is caught completely off-guard when his girlfriend, Summer, suddenly dumps him. He reflects on their 500 days together to try to figure out where their love affair went sour, and in doing so, Tom rediscovers his true passions in life.
A plastic surgeon, romancing a much younger schoolteacher, enlists his loyal assistant to pretend to be his soon to be ex-wife, in order to cover up a careless lie. When more lies backfire, the assistant's kids become involved, and everyone heads off for a weekend in Hawaii that will change all their lives.