During a celebratory outing in Las Vegas, Shane Rawlings, his sister Sallie, and his best friend Liam Blackwell, wind up in a tragic car accident. Liam dies and ten months later Shane, a high school teacher, lives life isolated on Bainbridge Island, riddled with guilt over his friend's death. Emma Jacobs is a famous actress embroiled in a scandal by her cheating ex-boyfriend. She escapes to Bainbridge Island and meets Shane by chance at the local grocery store. He is unaware of Emma's celebrity status. Shane begins receiving several mailed index cards each week. A task is detailed on each card that challenges him to venture out of his self-imposed exile. Emma helps him with each assignment, such as diving off a cliff and playing an instrument in front of a live audience. Shane and Emma grow closer with each completed task. By the fifth date, they are physically intimate and the evening progresses with a motorcycle ride, a bathtub massage and an impromptu musical performance.

Emma Jacobs is a famous actress embroiled in a scandal by her cheating ex-boyfriend who escapes to Bainbridge Island and meets Shane by chance at the local grocery store. Shane and Emma grow closer with each completed task until Emma's agent arrives in town and pulls her back to Los Angeles. Shane flies to Los Angeles, hoping to persuade Emma to take him back. Faced with disapproval from outsiders, Shane and Emma fight for their love and his healing.