Down and out, Erica Strange is desperate to change her life and takes up an offer from a mysterious therapist, Dr. Tom, who sends her back in time to relive a notable high school regret.

Erica settles for a dead-end job that can pay the bills. She is sent back to her university days to join an exclusive secret society with hope that doing so will finally set her onto the right path.

Eternally-single Erica brings best friend Ethan to pose as her boyfriend at her high school reunion. She begins to understand the source of her relationship troubles with men.

In order to conquer her fear of confrontation with her new “bully” boss, Erica is sent back to her first semester of university where she learns to finally stand up to Professor Lozar.

Tired of being treated like a child, Erica confronts the source of her reputation by returning to her Bat Mitzvah only this time she will prove herself as a woman.

Erica is worried that her sister Samantha is marrying the wrong man. When she goes back to prevent Sam and Josh from getting together, Erica learns a secret that threatens her relationship with Sam.