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 the 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.
Erica goes all out for Judith's baby shower, to prove she's got what it takes to be a Godmother. But when things don't go as anticipated, Erica is sent back to her Bat Mitzvah, and realizes that being a responsible adult means knowing who you are and having the courage to be that person.
Moments before Sam and Josh are set to walk down the aisle together, Erica struggles with 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 five years ago...
With the stress of work and family life weighing heavily on Erica's shoulders, Dr. Tom gives her a break, sending her back to a perfect day.
With Yom Kippur on the horizon, Erica seeks forgiveness from Samantha. But forgiveness is hard to come by, and before Erica can expect it from her sister, she must learn to forgive her parents when she goes back in time to better understand what tore them apart.
Erica's in love, but not necessarily with whom she expected. She's sent back to 1999 to re-experience her intense romantic connection with good friend Cassidy, the girl next door. But when Erica takes their relationship to the next level, she discovers that with love, it's all or nothing.
When Erica's hatred for long-time frenemy, Katie, erupts to the surface, she returns to the source of their long-standing feud to discover what really tore these once best friends apart.
Charged with supervising the launch of Katie's new book, Erica turns into a complete control-freak. She soon realizes that her need to control might be standing in the way of taking her relationship with Ethan to the next level.
In order to learn how to step outside the box and be something more than the fun-loving girl next door, Erica is sent back to a time when her narrow-mindedness and cowardly behaviour hurt someone dear to her.
Erica returns to her greatest regret, her brother Leo's death, only to discover the hard way that there are consequences to playing God.