After graduating high school, sheltered Kyler Smith leaves her comfortable life in Alabama to spend the summer before college in beach-front Ashton, Connecticut. She plans to mix things up over the summer and become more like her eccentric, cocky best friend, Natalie. She starts off by making a list of things she should have done in high school, but never tried. On moving day, it appears that Natalie has the similar plans for Kyler. Together, they try to find someone for Kyler to lose her virginity to by the end of the summer. However, they aren't the only two that are scheming. The intimidating local artist with the bad reputation, Brant, quickly makes a deal with Kyler. He will have sex with her by the end of the summer, but there is one condition: she has to learn what a healthy relationship is like by being with him. After thought, Kyler agrees to Brant's proposition. Although she does have a lot of questions concerning why he would make an offer like that without barely knowing her. Kyler isn't left with much time to ask herself what Brant is hiding before things get more complicated, leaving Kyler to battle against her own conscious. She never imagined that the perfect summer she planned with her best friend as a kid might be the very thing to stretch their friendship to the limit.