The approaching Rawley Summer Cotillion inspires Will to approach the girl of his dreams, Caroline Busse, but when she already has a date for the dance, he invites Bella to go with him, although both their eyes are distracted by others. Meanwhile, Scout tries to make the most of his evening with Paige, and Hamilton and Jake reveal secrets in an intimate moment.

Will finds himself in the enviable position of poetry tutor to the girl of his dreams, Caroline Busse, but his nightmare begins when he learns that an obnoxious upperclassman, Ryder, also has his eyes on the prize. Meanwhile, the surprise of a lifetime comes for Bella on her 16th birthday, and rumors fly about Hamilton and Jake's clandestine love affair.