Thirty-two year old Erica Strange is bright, educated and pretty, but she's had a bad life, self admittedly due to the many bad decisions she's made over her adult life. On the day that she meets self-proclaimed therapist Dr. Tom in the hospital, Erica has had the latest in a string of bad days: she gets fired from her dead end customer service job at an insurance agency for being too bright; she gets dumped by her latest boyfriend who she met over the Internet; and she gets hospitalized for drinking a specialty coffee containing nuts, she being deathly allergic to nuts. Feeling overwhelmed by the pity showed by her family, Erica decides on a whim to enlist the help of Dr. Tom, who guarantees he can fix all her problems if she commits to his service. Unbeknownst to Erica, Dr. Tom is not quite who he appears. Erica provides Dr. Tom with a long list of those bad decisions which she most regrets, those she terms as keeping her awake at night. From the list, Dr. Tom chooses Erica's ... Written by Huggo

In her current job search, Erica runs into Antigone Morris nee Kim, a rival from Erica's university days. Antigone's professional life seems successful, her success based in large part to her connections through Literati, a secret society from university, Literati members who support their own. Erica was invited to join Literati, but her gut told her at the time that if their pseudo-Gothic initiation ritual was anything like the club, it was not for her. Erica now regrets the decision not to join. Dr. Tom sends Erica back to second year at university when she was invited to join the group. Although Erica still realizes that Literati is in spirit not what she would be attracted to, she decides that one of the benefits of Literati membership is to discredit Claire, the now wife of her best friend, Ethan. Erica never really liked Claire but Erica's want to discredit Claire is based more on what she now knows about what Claire did to Ethan in present times. Erica's new decision has ... Written by Huggo

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. Written by Huggo

Erica feels likes it's going to be a good day. She is basking in the aftermath of her first kiss with Ethan, with who she sees a potentially happy future despite their long friendship and him still being married to Claire. And she's starting her new job - albeit in an extremely junior position - as an editorial assistant at River Rock Publishing. Her day quickly goes downhill when she meets her new boss, Julianne Giacomelli, a young, controlling, confrontational, passive-aggressive bully of a person, who seems to relish in embarrassing Erica. To Erica, Julianne is a younger, female version of her first year university creative writing professor, Antonin Lozar. Because of the emotional scars from that class, Erica has never done any creative writing since. Dr. Tom sends her back to Professor Lozar's class to defend what she considers a true indication of who she is as a person, her poem entitled Snowflakes. Will her new experience with Professor Lozar prepare her to handle Julianne? Written by Huggo

Erica and Judith have a falling out over a misunderstanding regarding who Judith has chosen as her baby's godmother. Erica not being chosen reinforces her own negative perceptions of not feeling grown up. Dr. Tom sends Erica back to her Bat Mitzvah, appropriate not only because it was supposed to be her official transition into adulthood, but also that she walked out on that party just like she did with the baby shower she just hosted for Judith. Erica's Bat Mitzvah, on a theme of the movie Dirty Dancing (1987), never lived up to hype and excitement she felt before the party. But Erica's adult sensibilities can now relive the party for what it was. She can also learn that an official event like a Bat Mitzvah does not nor need not have to mean she should feel like an adult. Written by Huggo

In the lead up to Sam and Josh's wedding, Erica and Ryan, Josh's best man, have been dating, publicly announcing the fact, making Erica uncomfortable. The fact that Ethan and Claire may have reconciled isn't helping either. But topping Erica's uncomfortable list in the relationship department is Sam and Josh themselves, their relationship which she just does not understand. She can't help but feel that they are making a big mistake in getting married. She feels even worse when Sam herself expresses the same doubts just before the ceremony. With Dr. Tom, Erica dictates to him where she wants to go: August 13, 2003, the day that Sam and Josh broke up for the one and only time during their relationship. Then, Erica convinced Josh to reconcile. This time, she will do no such thing. Dr. Tom obliges Erica's wish. Back at that break up, Erica directly learns from Josh not only the nature of Sam and Josh's relationship, but what is truly in his heart and why he has always acted with animosity... Written by Huggo

Erica is facing a lot of stress in her life. Sam is no longer talking to her and never wants to see her again. Marcus Stahl wants to renege on the book deal of writing his memoirs since he can't visit that dark place in his past. Because she feels her sessions with Dr. Tom have so far made her life worse than better, she wants to quit. However, Dr. Tom offers her a gift because of her stress: he will send her back to any day she wants where she was the cause of the day being perfect. She chooses a time as a teenager, taking a day trip to Toronto Island with Leo and Sam, to get away from their arguing parents who looked to be on the verge of divorce. One importance of this day is that, as Erica states, it is the last big 'hurrah' between the three of them before Leo died. She vows not to change a thing about that day. However, her thirty-two year old sensibilities may factor into what she now decides to do. And any small change to the day may alter how perfect it was in her memory. Written by Huggo

It's Yom Kippur, and there is much pressure within the Strange family for everyone to reconcile, especially Erica and Sam, but also Gary and Barb, the latter who has has always resented her husband's decision to be a rabbi, and Erica and Barb. Dr. Tom sends Erica back to Yom Kippur 1997 - the year following Leo's death - when Gary and Barb were having a fight over his spending so much time at the synagogue, with Erica siding with her father. In addition to Barb wanting a divorce following that incident, Erica and Barb's relationship has since been an antagonistic one. Erica vows this time to stay neutral in her parents' argument. Although she starts off being neutral, Erica learns more behind her parents' marital woes, which may change her attitude towards both. Dr. Tom tries to provide further insight by sending Erica even further back to 1974, to a hippie commune retreat that Gary and Barb went to shortly after they got married. Written by Huggo

Erica is emotionally confused. On their three month anniversary, Ryan tells her that he loves her, a place where she is not yet at. And she still seems to have unresolved feelings for Ethan, despite he who is trying to reconcile with his wife, Claire. Ryan can sense something still lingering between Ethan and Erica. To resolve her current conundrum, Dr. Tom sends Erica back to a previous relationship with Cassidy Holland, one that ended just before Y2K. Erica emphatically states that Cassidy is the most amazing woman she has ever met, and a person on whom she had a crush. Although Cassidy was openly gay, Erica states her feelings were not in a romantic way despite she knowing that Cassidy wanted something more between them. This time around, Erica wants to ensure that Cassidy knows that she is straight so that they can deal with the issue head on and thus maintain their friendship. But this revisit to her past makes her truly confront her feelings for Cassidy, and how that may impact ... Written by Huggo

After Erica's declaration of love to Ethan and his response that he can't feel the same as he's still married, Erica has been avoiding him. Erica feels even worse since her so called friend/nemesis since the age of five, Katie, is in town. Katie manages to maneuver a deal with River Rock Publishing to write a book around Julianne's latest idea - Katie was planning on using Erica's failed love life as its core. Dr. Tom decides to send Erica back to high school, to an unsanctioned Halloween party held at Casa Loma, where Erica, Katie and Judith worked. Although the party was Katie's idea, Erica was the only one who had a key to get into the complex. Katie was fired over the incident, and Erica never took any responsibility, which she feels ruined her friendship with Katie. Erica vows not to hold the party at Casa Loma this time to save her friendship with Katie. But going back, Erica may not be able to change the past. She also learns the true nature of her friendship with Katie. Written by Huggo

Erica has much on her mind. She wants to be there for Judith, who is facing new motherhood issues. She has been given the responsibility of organizing the launch of Katie's book at a book fair. But in this task, she unknowingly has turned into her worst nightmare: a replica of Julianne. And she is still trying to avoid Ethan, who knows that she's avoiding him. There may be a connection between the control she's exerting in the book launch and the control she's trying to exert in a relationship between herself and Ethan. As Dr. Tom allows her to add to her list, she wants to go back to the night of her high school reunion when she and Ethan kissed, what she feels is the beginning of the end of their friendship. Dr. Tom warns her and she realizes that taking back the kiss will not remove the feelings she has for him. Although Erica does manage to avoid the kiss, she quickly realizes that going back in time may actually provide an opportunity to rewrite totally the nature of her and ... Written by Huggo

Erica should be happy as she has just been promoted to junior editor (pending sign off by Galvin and a final stamp of approval by Julianne) and is in the new romantic phase of her relationship with Ethan. But Ethan is having problems with Claire, who is threatening to sue for spousal support, despite coming from a family with money. And Erica is facing challenges in her new job, namely the aspect of firing people, most specifically writer Linda Kaplan, a woman who Erica has never even met. Since Erica feels that firing people is outside of her comfort zone, an upset Julianne sends Erica to a management seminar, a seminar in which Erica fails miserably. Erica likens her current work predicament to a past relationship with Ivan Frankel, who she called IF. IF was a man she abandoned without even a goodbye as she did not want to confront him about his Vampire LARPs (Live Action Role Plays). These LARPS were an activity in which he was passionately involved but Erica didn't want to partake... Written by Huggo

Erica's life is finally going great, both personally and professionally. But the fact that December 13th is approaching is weighing heavily on her mind, that date being the anniversary of Leo's death, which is still her biggest regret in life. Leo died at the age of 21 in a barn fire at her grandmother's farm, the fire that appears to be an accident of Leo's own doing. The farm is now the unofficial grave site where the family visits only once a year to mourn. Erica wants things to change, to make Leo's memory more of a happy thought than a somber one. Her idea is to rebuild the barn as both a cathartic exercise and a standing memorial to Leo. This task ends up being difficult for Barb, who cannot let go of how she grieves for her son. Before sending Erica back to that time to allow her to say goodbye to her brother, Dr. Tom stresses to her that her therapy does not allow her to play God to bring back the dead, and that there are dire consequences if she tries to do so. Once back, ... Written by Huggo