Erica Strange is approached by a mysterious therapist who sends her back in time to relive one of her high school regrets.

Erica is torn between following her career dreams to work in a literary field and settling for the secure option at her uncle's bridal factory. Her trip back to University when she was approached by the esteemed secret society Literati teaches her the value of following her heart.

When Erica brings Ethan to her high school reunion to pose as her pretend boyfriend, she must relive her first sexual experience in Muskoka to understand and overcome the source of her relationship troubles.

In order to conquer her fear of confrontation, Erica is sent back to her first semester of University to finally stand up for herself against the daunting Professor Lozar.

When she is treated like a child, Erica must confront the source of her reputation by returning to her Bat Mitzvah, only this time she will truly prove herself as a woman.

Moments before Sam and Josh are set to walk down the aisle together, Erica struggles whether to reveal to her sister her true antagonism toward Josh. If only she hadn't helped them get back together after a near break up three years ago.