Divorced with two kids, Jackie is facing her fortieth birthday, and she is depressed. Her friend decides that they should go to Hawaii to celebrate but backs out once they're at the airport. Although full of trepidation, Jackie goes solo. The trip turns into a series of firsts, including surfing lessons and sex with her young, hunky instructor. Over the next few months, she can't get over him, and makes several return trips to the island. When her daughter is hospitalized while Jackie is away, she breaks off the affair. Riddled with guilt, she is forced to figure out if she is willing to risk everything for a chance at newfound happiness.