Erica, feeling like a failure since high school, decides to ask Ethan, who is going through a divorce and recently moved back to Toronto, to escort her as her make believe boyfriend to her high school reunion. There are two people who Erica is not looking forward to seeing at the reunion. One is Katie, who has always gotten under Erica's skin. But the more important one is Zach Creed, the popular kid to whom she lost her virginity. Beyond the fact that the sex with Zach was bad, he humiliated her after the fact. Erica feels that experience with Zach has negatively tainted the way she now views potential boyfriends. Dr. Tom gives her the opportunity to redo that experience with Zach. But based on what she sees at the reunion, the one person that Erica may instead want to lose her virginity to the second time around is Alex Berlin, who was then the quiet class geek. Her time with Alex both then and now makes her realize who is really important in her life.
—Huggo