Jen Reed is afraid of commitment and has managed to push away the man she loves. Feeling that he's better off without her, she's bent on getting over him no matter what. To Jen, this means going on multiple dates until Brian is erased from her heart. But it's not working. Therefore, she agrees to participate in the ultimate distraction: a destination wedding in Hawaii. However, fate has other plans.

Brian Hicks is giving his college-relationship another go but for all the wrong reasons. With a broken heart and regret behind him, he's determined to get over the woman he still loves. To Brian, that means focusing on work, pleasing his new girlfriend, and avoiding his ex-girlfriend, Jen, as much as possible. Therefore, the last thing he wanted was a week-long vacation trapped with both his new girlfriend and the one he can't get over.

A surprise reunion at a destination wedding in Hawaii will alter the course of Jen and Brian's lives, challenging deeply held beliefs about each other and, ultimately, themselves. As they try to move on with their separate lives, reminders of their past relationship begin to surface until it explodes into a breathtaking event.