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- Julianne and Brent hit a possible obstacle in their relationship, namely Brent's dog Duchess and how well, or more precisely how badly the two females get along. Meanwhile, Erica is beginning to have a series of scattered visions which is giving her massive headaches. Dr. Tom informs her that the visions are a sign that she is now a full fledged therapist, the visions, which will become clearer as time goes on, identifying who her potential patient will be. Erica is unprepared for this news, and feels she will need Dr. Tom's guidance now more than ever in navigating through her early days. That is why Erica is even more unprepared for Dr. Tom's other news: that he has decided to retire, the implication of which is that he must sever all his therapy relationships forever, including with Dr. Naadiah and his patients. Erica is devastated by this news, and as such Dr. Tom contemplates delaying his retirement until Erica feels she is ready to live all facets of her life without him. To show Erica what Dr. Tom's delay means, Dr. Naadiah reunites Erica with someone from her past in his present situation.
- Erica's life seems to be back on track. 50/50 Publishing's future seems bright. Brent wants to extend a permanent olive branch to Julianne - and by association Erica - due in part to their now closer working relationship. Julianne is still somewhat suspicious as Brent will not tell her why he originally stabbed her in the back. Back with Erica, she is in a budding relationship with Adam. And all of her family - Barb, Gary and Sam - are also in happy places in their lives. But Erica's life takes an unexpected turn when, after waking up after her first ever lovemaking session with Adam, she finds that she is back in the hospital during the time when she first met Dr. Tom. Populated by familiar faces in different positions, such as Julianne as a nurse, Dave as an orderly and Dr. Tom as Dr. Wexler who is her physician and not her therapist, Erica's new reality is that she has just awaken from a two week coma from her nut-allergy induced anaphylactic shock. The implication is that her therapy with Dr. Tom has been a dream. As Erica tries to cope with what she sees as this setback, she receives a visitor from her past who tries to make her understand what's going on. Regardless of if what she is experiencing is indeed her reality, Erica has to come to the understanding that she still has the lessons learned from therapy - imagined or real - to start the process of bettering her life all over again.
- 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, Erica finds that knowing her brother is going to die and not doing anything about it is more difficult than she could have ever imagined. Erica learns the hard way that there are extreme consequences in every aspect of her life to her decision to try and save Leo.
- Erica is feeling conflicted about her decision to start her own publishing company with her fellow fired River Rocker Julianne, their first planned book being Seth Newman's manuscript about escaping from a cult within which his family still lives. Although the business was Erica's idea, Julianne is equally as excited about the prospect. Ethan, however, wants Erica to be more cautious in whatever her next career pursuit. Dr. Tom gives Erica a test to follow her gut feeling. As Erica is unable to complete this test, Dr. Tom sends Erica back to graduate school, when Erica mistakenly sent a nasty email to her brilliant but difficult thesis adviser, Dr. Audrey Hogan, the department head. Erica vows not to send the email the second time around. Regardless of the email, Erica feels that Dr. Hogan hates her. But Erica comes to understand what she is supposed to learn on this visit back. With this new found knowledge, Erica tries to assist Kai, who thinks that he will soon be sent back to resume his real life. But she also makes a decision to change a fundamental aspect of her own current life, and walks through a door to an unknown future.
- Kai returns. Based on what he told her last time he saw her, Erica is certain that this trip is the one where the two of them will have sex. Because the encounter already happened in Kai's past, Erica is unsure if she has the ability to change that if indeed she does not want to have sex with Kai, which based on circumstance could not blossom into a full fledged relationship. Erica brings this conundrum up at group therapy. Beyond what Erica sees as a slight glimpse of jealousy on Adam's part to this news, Dr. Tom reacts in such a way that angers Erica and that could threaten her therapy with him altogether. What Erica is unaware of is that Dr. Tom is dealing with something in his own life out of need. Dr. Arthur has been concerned that Tom has been hiding behind work rather than take time to reflect and enjoy his own therapied life. The situation which he and his wife Marjorie are facing is the return of their daughter, Sarah, who is very much in need of help but whose actions show that she is unable or really unwilling to clean up her life. This situation makes Tom feel helpless, unlike how he feels when he is dealing with his patients. Meanwhile, Sam has gone from one extreme to another in her public dealings with Lenin, this time overcompensating for their professional disparities.
- Things around Erica are not going well. Sam, who is still staying with Erica and Ethan, has just been served divorce papers by Josh, who wants to take her for everything. And Erica loses two important people in her life. First, Brent no longer wants to associate with her as he sees them as being on opposite sides of a Cold War. And second, Kai no longer wants to see her after her admission to him that she has feelings for him. Not wanting to fall into what he sees as the bad life he lived in 2019, Kai quits his job at Goblins without telling Erica in hopes that she can go on with her happy life with Ethan. Erica, in her regular therapy session, wants specifically to deal with the issue of Kai, which Dr. Tom refuses, he stating that her therapy is about her and not Kai. After a fight, Erica walks out of her session. Their fight reminded Dr. Tom of his own strained relationship with his street-wise daughter, Sarah, whose whereabouts he now does not know. To help him understand what is happening between himself and Erica, Dr. Tom is sent back by Dr. Naadiah to his last meeting with Sarah. This trip back may fundamentally change Dr. Tom's relationship with Erica, and by association Kai.
- Erica receives a surprise visit from someone she never expected to see again: Kai. She figures he is on a rogue mission as this visit seems against the rules of therapy. Regardless, he has much news for her, the most important being that he looks for her in the year 2019 and can't find her. Erica believes the worst for herself, meaning death for her in 2019 at age 42. As Erica progresses through the day, she can't focus on anything else besides the possibility of dying at such a young age and wanting to find out for sure what really happens to her in 2019. As such, Dr. Tom sends Erica back on a Groundhog Day (1993) scenario, reliving a certain time of her life over and over again, perhaps for eternity or at least until she figures out what lesson Dr. Tom is trying to teach her. But as he denies Erica her initial request, Dr. Tom does exactly himself what Erica requested for herself, which brings up concerns with Drs. Naadiah and Arthur. And Barb's actions may be a role for Erica to follow as Barb tells her of her breast cancer.
- Because Erica reneged on her vow not to try and save Leo from dying, Dr. Tom quits being her therapist. He refuses to see her. Erica in turn refuses to continue with therapy with her new assigned therapist, Dr. Naadiah. Erica feels that perhaps she doesn't require therapy anymore. She is in a committed, loving relationship with Ethan. She got the much coveted job editing River Rock's latest high profile book (much to Brent's chagrin). And her relationship with her family is the best it's ever been. But Erica learns that there is a cost to quitting therapy. That cost is helping another lost soul. The year is 1998, the place a Coyote Ugly (2000) type bar. Her down and out client is someone named Tom Wexler, who Erica knows but under a slightly different name. Before Erica can help him, she has to understand how Tom Wexler became the man he is. But what he sees as Erica's meddling in Tom Wexler's life may bring Dr. Tom out of his self-imposed silence.
- Erica and Ethan's relationship hits a rough patch. They have been arguing a lot without Erica really knowing why. In turn, Ethan seems to be running away from her without telling her of that fact. This relationship is becoming reminiscent of Erica's previous relationship with Malcolm Abrams. Once her best friend during their senior year when they were both camp counselors, the two became romantic after which he suddenly broke up with her. The break up caused a war of one-upsmanship which Erica eventually lost. The second time around, Erica vows not to play these games with Malcolm after the break up, regardless of why he did it. However, she can't hide her disdain and her need to get back at him once the games start happening again. But when she learns the reason for the break-up, she realizes that none of this would have happened the first time around if they just talked. Dr. Tom also convinces her that perhaps the current non-communication with Ethan is a two-way street despite she believing she has been totally honest with him. Meanwhile, Josh makes a unilateral decision in his and Sam's life. Brent takes a bold step in his professional life at River Rock. And Erica decides to speak to Kai the barista about what she thinks she saw at the coffee house.
- Beyond Rachel knowing, Julianne isn't yet ready to tell the world, let alone Erica, that she and Brent are a couple. Although Brent respects Julianne's wishes, he doesn't much like it. Erica also isn't ready to tell the world that she and Kai are now dating. Their relationship faces its own challenges with Kai being officially from the future. Being as such, Kai has certain knowledge about what will happen in Erica's life. Although he knows he isn't supposed to tell her anything about the future, the temptation to pass along monumental news may be too difficult to keep. This news does affect the way Erica deals with her present, especially with regard to an offer by Scott Galvin which Erica would have dismissed had she not known the news. However, a visit from an unexpected person from her future may shed some light on what the future may hold for her and what that means for her present. Dr. Tom, on the other hand, isn't allowed to divulge the nature of his work to Amanda, which may place a wedge between the two as him hiding parts of his life from her was the reason for them breaking up on their first go around. Meanwhile, Sam is overdue and will do anything to go into labor. As such, she makes a special request of Lenin, who isn't sure if he can accommodate Sam's request.
- 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.
- Sam's getting married and Erica's maid of honor. Erica has doubts about the groom. She asks Dr. Tom to go back to when they broke up and Erica regrettably fixed it.
- Erica travels back to December 1999, when her best friend was a lesbian.
- Attempting to alleviate the awkwardness in her friendship with Ethan, Erica travels back five months to the night of her high school reunion.
- Erica's life seems to be bound by rules and conventions, rather than acting on what may be deep in her heart. Ethan has just moved in, yet he feels threatened by Erica's relationship with Kai. Erica, with Ethan in tow, needs to do some research for her sex book at a bona fide sex club, where many social rules are broken. To allow her to feel what life is like without these conventions, Dr. Tom gives her the entire day again, this time how she wants it to play out. The only thing that will exist on her day after the fact is her memory of it. So she lets loose, and spends much of the day with the only person who can really appreciate it, Kai. Erica learns that even though nothing during her day is real, it feels like it's real - the good and the bad - and that she'll know what others truly believe and think after the day is over.
- Barb has just started dating a new man named Norm, for which Erica is happy. Erica volunteers to pass the news along to her father, who seems less than thrilled despite stating otherwise. Erica talks Barb into introducing Norm to the family at an upcoming family bris, at which Gary is to act as the mohel and a reluctant Erica the sandak, a role to which she agrees if only to feel more connected to Gary at this pivotal time. Meanwhile, with Dr. Tom's knowledge, Erica is called into Dr. Fred's office to discuss a roadblock that Kai is facing in his therapy. What little Erica has been able to glean directly from Kai is that he is unhappy with his therapy. Kai, however, knows nothing about this intervention with Erica. Erica is unsure if she should get involved, but decides at least to hear Dr. Fred out and hopefully to understand Kai better. Unexpectedly, Dr. Fred sends Erica to 2019 to what she thinks is Kai's future as a famous rock singer, a future if he discontinues therapy. This experience is not quite what it initially seems. But from this experience, Erica does learn from what Kai is running and why he wants to turn his back on therapy. But more importantly, Erica learns that she is not Kai's savior, nor is she her father's.
- 2009–201145mTV-PG7.7 (83)TV EpisodeErica is on strained terms with Kai because he had sex with Sam after she told him to look after her. It doesn't help when Erica tries to avoid him, but still runs into him both in her professional and personal life. She's not sure what the connection is to her current problems, but Dr. Tom decides to send Erica back to a time in high school when she and Leo had a house party, which resulted in Gary's beloved "mid life crisis car" getting trashed. Gary was never more angry with her than over that incident, and his and Leo's relationship never recovered. In going back, Erica believes that Leo's blind loyalty to his friend Robin is the cause of the car getting destroyed and for Leo and Gary's fallout. But Erica ultimately learns to see the truth behind the façade. She has to apply that truth when Kai asks her a question.
- The Cold War at River Rock Publishing between Brent and Julianne continues. Erica, editor of "The None" - Katie's new book - is falling on Julianne's side of the war, despite not wanting to have to choose between the two. When a traumatic event occurs to Erica at River Rock, Dr. Tom decides on Erica's tenure at a dot com in 2001 as the next item on her list to revisit. Erica quit her job at meandyoumakes2.com just prior to it being sold. If she had stayed at the dot com through its sale, she probably would have made millions. Dr. Tom sends her to an alternate reality first in 2004 and then in current day 2009 as if she had stayed at the dot com through its sale. Erica is unsure if this visit will become her new reality. But through this process, Erica learns that life experience is important to personal growth. She uses this knowledge to reinvent herself, but not without some obstacles. Meanwhile, Kai is being pressured by Travis to embark on the path which ultimately led to Travis' suicide. Kai tries to change this path to save Travis' life, but ultimately Kai comes to a more important understanding.
- It's been three weeks since Erica broke up with Ethan, yet whatever she does, she just can't stop thinking about him. Even though she initiated the break-up, she feels a double loss in that he was both her lover and best friend. She has to figure out how to move on without him. On the sexual front, she seems to be running into more men to whom she is attracted, some who look like Ethan. With some, she even contemplates having sex. And she runs into old boyfriend Ryan, with whom she thinks she can have a platonic relationship - the male friend part - now that she and Ethan are no longer together. The therapy group have their own opinions, despite Erica initially not believing she needs their help. She comes to the realization that she does need help to figure out if leaving Ethan was the right thing to do. Dr. Tom thinks there is one person in Erica's past who knows exactly what Erica is going through and may be able to help. Meanwhile, Samantha starts a new phase in her life, while Barb is at the end of one.
- 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.
- In an attempt to mend her friendship with Katie, Erica travels back to Halloween 1993.
- Doctor-in-training Erica is dismayed to learn that her first patient is someone that she knows: her soon to be ex-brother-in-law, Josh MacIntosh, a man she neither understands or likes. Despite she realizing that Josh needs help, Erica hates him even more after Samantha's vitriolic verbal attacks about their bitter divorce proceedings. To help Erica help Josh, Dr. Tom sends her back to the incident when she first realized that she hated him, which was a trip in 1998 by Erica, Sam, Josh and Jenny to Fort Lauderdale to visit Erica and Sam's grandmother. Erica tries to use this trip revisited as her opportunity to make a real connection with Josh. But Erica learns that she not only has to make a connection, but in the process truly understand what Josh is all about as a person, which may end up backfiring in her face. A reminder of another past incident between Erica and Josh may be able to provide Erica that much needed perspective.
- Erica attends high school reunion, bringing Ethan as her "boyfriend". Dr. Tom takes Erica back to 1994, just before losing her virginity to Zach.
- Risk-averse Erica (Erin Karplunk) has decided that in not taking risks, she is often standing on the sidelines wondering how much more could have been achieved. Testing the sexual boundaries with Ethan (Tyron Leitso) may be one thing, but the bigger risk is the opportunity to write the sex book instead of edit it, which is what Julianne (Reagan Pasternak) is offering her. If she accepts, that means she has to give up her stable editing job. This decision is reminiscent of the year after the completion of her undergraduate degree, when she and Jenny (Paula Brancati) were going to go to Taipei for the summer to teach English but otherwise just "wing it." Erica chickened out at the last minute, which she has since regretted since it ended up being the worst summer of her life working at a boring government job instead. When Dr. Tom (Michael Riley) sends her back to that trip to Taipei, Erica learns that risk has its uncomfortable moments, and its extreme highs and lows. She also learns that taking risk should not absolve one of responsibility. And taking a risk should be about achieving what one really wants. With others, Brent (Morgan Kelly) takes another step to see if the risk he took at work pays off. And Jenny takes what she sees as a risk, but is really just her predictable course of action.
- It's Thomas Friedken's 45th birthday, and Julianne decides to give him a key to her apartment as a birthday gift. Erica stumbles across something that makes her think Julianne's gift may not be the best idea, but doesn't know if telling Julianne this secret is the best idea either. Dr. Tom thinks this situation is reminiscent of a time when Erica was a high school senior. Jenny had as her target a quiet but overachieving classmate named Fiona Watt, who Jenny tormented until Fiona left school never to return. Erica knew what Jenny was doing, and even to this day feels that she herself was a part of that torment because she knew and did nothing to stop it. Going back to high school, Erica believes she has fixed the problem between Jenny and Fiona by bandaging the symptoms, until she learns the underlying reasons for Jenny's actions. This understanding makes Erica realize what she has to do with Julianne and her current situation, and what she has to do with the tense situation between herself and Kai stemming from Erica's do-over day.
- It's the end of a bad day for Erica. First, she catches Ethan masturbating to cheesy computer porn, this issue which Erica cannot understand. Second, Julianne has a meltdown in front of Erica about Friedken's strong arm tactics after she humiliated him in front of the rest of the staff. And third, Sam arrives back in Toronto on Erica's doorstep announcing that she's left Josh in London without even telling him. On top of these issues, Erica receives a visit from Dr. Fred asking for continued assistance in Kai's therapy, which Erica feels at the present time unable to provide. Although Drs. Tom and Fred argue about their respective therapies - all stemming from Dr. Fred's unauthorized visit with Erica - Dr. Tom takes Dr. Fred's advice to move Erica's therapy to the next level. Erica is tasked with solving all the problems of this past day on her own. She feels what she needs to do is listen to what her gut is telling her, and she hopes all those associated will do the same.
- 50/50 Publishing's future seems a little brighter now that Brent has provided them with Jay Manuel's exposé on the fashion world as their next big book, and as Julianne ghost top edits Thomas Friedkin's latest book for Brent. Meanwhile, Erica is feeling excited by Adam's implication, partly through his kiss on the deserted island, that he is indeed interested in her romantically. They even have a date scheduled to talk about what the kiss means. After a group therapy session, Erica decides to follow Adam through his exit door to talk to him, but she finds him at the end of a romantic tryst with Beatrice. Erica has no idea who Beatrice is, but only knows that she feels betrayed that he is having sex with another woman while expressing interest in her. Erica's cold shoulder treatment to Adam changes when he explains who Beatrice is. As Adam proceeds with what he believes is his destiny with Beatrice now with Erica's understanding, Adam runs away from Beatrice after a lovemaking session, but is uncertain why. As such, Dr. Tom sends Adam back to a time with his family, which had the pattern of physical abuse by his father on his mother, who in turn emotionally abused Adam in her dependence on him. As Adam learns how to break the pattern, he understands what he needs to do in his current life with Beatrice and Erica. Elsewhere, Barb has some good news regarding her health, and makes some decisions about her future, specifically with regard to Gary.
- 50/50 Publishing is hosting an all-inclusive Christmas party. The self-professed queen of Christmas, Julianne, is taking charge to ensure that everything for the party matches the exacting standard of a Giacomelli Christmas. On the flip side, Adam, who attends the party nonetheless, has never had a merry Christmas, and he seems determined not to partake in the traditional Christmas festivities just to please others. In the middle is Erica, who, coming from Jewish background, has never officially celebrated Christmas with her family, but has observed its secular traditions as an adult as they surround western society. Erica will even miss the traditional first night of Hanukkah with her family because of the party. Regardless of Adam's feelings, Erica is determined to show Adam that Christmas, with its associated traditions, can be a happy time. As such, Dr. Tom sends Erica to three holidays past: first to a Giacomelli Christmas as a teen-aged Julianne, that experience which is a much tenser version of what Julianne had described; second to a Strange holiday past when Erica was twelve and who, along with her siblings, wanted so much to partake in the Christmas rather than Hanukkah traditions; and third to Adam's last Christmas day, which was spent with what he considered his best friend at the time. These experiences show Erica what is important to show not only Adam, but everyone, in making this indeed a happy holiday season.
- Despite still feeling the emotional pain of the situation, Erica is trying to move on with her life after Adam breaking up with her. She is trying to make herself feel better by wearing pretty but somewhat provocative clothes. Her friends believe her outward appearance matches how she is feeling inside. Coincidentally, she runs into Ethan, who is also a recent dumpee, this time by yet another strong, risk taking woman, much in the same vein of Claire and Erica herself. Erica sees that Ethan is always falling for the wrong type of woman, one who wants different things in life than he does. Erica believes that Ethan needs a female version of himself - sweet, quiet and socially conservative, someone exactly like a friend of hers from graduate school. So Dr. Tom sends Erica back to her graduate school days to play matchmaker for Ethan. This experience shows Erica what Ethan really needs in his current life. Meanwhile, Brent and Julianne have to decide how best to move on from their innocent or not so innocent kiss. And Dr. Tom wants Erica to discuss how she is really feeling about her break-up with Adam, which she doesn't want to do.
- Erica loses her job and boyfriend. A latte sample with nuts sends her to the hospital. She meets Dr. Tom. She consults him and makes a list of what went wrong in her life. She's suddenly back in high school, 16 not 32 y.o.
- Erica starts her job at River Rock Publishing, and travels back to April 1995 to confront her creative-writing professor.
- Erica's promotion to junior editor may be in jeopardy; she travels back to 2001 and participates in a vampire live action role-playing game.
- Erica walks through her chosen door and finds herself in a therapy group run by Dr. Tom.
- Adam runs into Beatrice, the woman who was shown to him as his loving wife in a seemingly happy alternate life. Despite being attracted to her and feeling a connection to her, he almost feels as if Beatrice is his destiny without any consideration on his part. Meanwhile, Erica and Julianne receive nothing but bad news about 50/50 Publishing's future in the wake of their moral decision not to publish The Purple Door. Declaring bankruptcy seems the most obvious choice. The one possibility to keep 50/50 afloat is to accept the offer to publish anything that will at least break even, even if it is something that Erica and Julianne feel is beneath their standards. But Erica receives an intriguing offer from her old college nemesis Antigone Morris née Kim to be considered for a Vice-Presidential position in her publishing firm, which if Erica proceeds would leave Julianne out in the cold. As Adam, among those in group therapy, has the strongest opinion about what Erica should do, Dr. Tom sends Adam along with Erica on a test: he places them on a deserted island, their only task to make it to the other side of the island. Erica and Adam are initially uncertain the lesson of the test, but as they struggle to find their geographic way, their life paths become clearer as they understand the lesson. Elsewhere, Sam and Lenin discuss their future in light of Lenin's standard six month move to another life, this time to Brazil. And Brent has something he wants and needs to talk to Julianne about, if only she will listen.
- It's the day of Dave and Ivan's wedding, and Erica, seeing two people in love, is reflective of her recent relationships. That reflection is also due in part to having Kai be her date to the wedding, yet seeing Adam there, not only for the first time since their break-up but with another woman as his date. She is lamenting the fact of always seeming to pick the wrong men, as even her relationship with Kai she eventually realizes can't last since they don't belong to the same point in time. Kai may be a little slower in coming to this realization as evidenced by a question he asks Erica. So when Erica lists to Dr. Tom the qualities of who she sees as her perfect man, Dr. Tom sends her to an alternate universe where she is in a relationship with exactly the man she described. Meanwhile, Brent is getting to the breaking point of his relationship with Julianne if only because of her reluctance to tell Erica of their relationship. And Dr. Tom, settling into his relationship with Amanda, contemplates his future as a therapist.
- Erica and Julianne learn that Brent is outbidding them for Seth Newman's book, not because he wants to publish it, but because he will do anything to ruin Erica and Julianne, who, to him, is purely the competition who he doesn't like. Erica wants to use diplomacy to deal with this situation. When Brent doesn't seem interested in diplomacy, the battle between 50/50 and River Rock becomes an all out war. Armed with incriminating information from Brent's past, Erica and Julianne decide to ruin Brent like he seems determined to do to them. Before Erica makes this joint decision with Julianne, Dr. Tom wants the therapy group's take on the situation. With a split decision amongst the group, Dr. Tom believes Erica can learn what her actions will lead to by visiting a time in her past when she went to visit Leo at university, specifically during rush week when he was pledging a fraternity which was two weeks before he quit school. The first time around, Erica did not spend any time with Leo as she hooked up with a man she met there, but she vows to spend all her time with Leo this second time around. She is initially unaware of how this revisit will help her, but with Adam accompanying her, she sees how Leo's situation with the fraternity makes her feel even more angry than she is with Brent. But only with a further visit to a time in Adam's past does she truly understand the nature of her revisit to Leo's rush week. Meanwhile, Sam finds some anti-anxiety pills prescribed to Barb and wants to find out the underlying issue for the prescription. And Erica receives an urgent visit from someone in her past.
- Scott Galvin's reign at River Rock brings an entirely different corporate mentality, where everything is driven by his testosterone laden sense. The men have to be dudes, and the projects they will be working on reflect Scott's own interests. Even the name of the company has been re-branded to The Rock. As hard as he tries for the sake of keeping his job, Brent just doesn't fit into this new corporate image. Erica's advice of pitching an idea that brings his own sensibilities into the testosterone world of The Rock gets Brent fired. After the fact, Erica realizes that her advice was just a tired old cliché. That's when she learns that Brent is her next patient. To understand what is happening to Brent, Dr. Tom sends Erica back to high school and her dealings with a Québecois exchange student named J.C. Paget, who stayed with the Stranges for her two week exchange and who just didn't fit in. To get J.C. off her back, Erica at the time told J.C. just to be herself, which made J.C.'s life even worse for those two weeks. This time around, Erica vows to help J.C. fit in. Erica learns that she can change J.C.'s outer appearance, but in doing so she may expose J.C. to situations with which she isn't equipped to deal. As it applies to Brent, he has to decide if he should beg for his job back which ends up being a bit more cutthroat than he imagined, or find something else more to his own sensibilities. Erica also has to decide how to apply what she learned to her own issues with Adam, who wants to buy a motorcycle against her wishes, and he who refuses to take salsa lessons with her.
- It's Erica's thirty-fifth birthday. She and Adam are back together, although they still disagree on certain issues, such as personal boundaries. Regardless, she's generally in a happy place in her life. She even gets a present from an unexpected source. The one negative issue in her life on this day starts when she catches Julianne and Brent locked in a romantic kiss at the office, which is her introduction to the fact of them being a couple. Instead of feeling happy for them, especially Julianne who she knows has been unhappy romantically of late, Erica feels that their romance is inappropriate for the office, especially as she feels as if the two will always side with each other against her in workplace decisions. To give her some perspective on the issue, Dr. Tom sends her back to Purim 1992, to revisit a regret and to have her deceased paternal grandfather - "Zayde" - as her next patient. Zayde visited from Montréal every year for Purim, his favorite holiday. But Zayde was stuck in a time and generational warp, and he treated then sixteen year old Erica and her siblings still like infants. Originally Erica ditched that Purim to hang out with her friends, but now regrets that since Zayde passed away a few months later. In sticking around for Purim this time around, Erica not only tries to help Zayde and in the process learn her own lessons about the Julianne and Brent situation, but she also reexamines a friendship lost. Meanwhile, Dr. Tom thinks he's made a decision about retirement, until Dr. Naadiah fills him in on the full implications of his decision.
- Adam learns that Hastings, his old boss for who he did his enforcing, has just died. At the wake which Adam reluctantly attends, many of his old enforcer colleagues, including his own younger brother Johnny who Adam got into the business, try to get him to return to this old lifestyle, which he declines but in such a way that those enforcer tendencies are still evident within him. Dr. Tom feels that Adam is now ready to confront that aspect of his life, and sends him back to his early twenties when he had a job with the "boss from hell", Sean, who Adam beat up after not being able to hold his temper any longer after the constant verbal abuse from Sean. That beating left Adam with a prison sentence, a criminal record and a reputation, all which led to his job with Hastings. He vows not to beat Sean this second time around but to walk away. However, in being able to walk away, Adam's life since that time fundamentally changes to an alternate reality he neither recognizes or embraces as he feels it is not within the scope of therapy. But Dr. Tom and the therapy group try to convince Adam that he is using those issues as an excuse not to pursue what he really wants in his current life. Meanwhile, Erica and Sam, wanting to support their mother, are feeling uncomfortable with her new "live life to its fullest" mentality.
- Erica goes back to 1995, her second year of university, where she is invited to join a secret society.
- Erica holds a baby shower for Judith, thinking that she'll be godmother. Dr. Tom sends Erica back to her Bat Mitzvah (13 y.o.) to help her understand her reaction.
- Erica is still trying to find out more about Kai, either directly from him or from Dr. Tom. Kai doesn't want to talk about therapy, but is glad to talk to Erica about other things, which she may need. She can't seem to talk to best friend Judith anymore as Judith is always caught up with baby stuff. This dynamic between herself and Judith brings up a previous issue between them when they were in university. Erica signed them up as Frosh leaders, something that Judith didn't really want to do. But Erica reneged on that commitment, leaving Judith to do it on her own. Ever since then, Erica has felt that Judith is the adult and Erica the child in their relationship. When Dr. Tom sends her back, he also sends one other thing with her: Judith's son, Max. Erica doesn't know how she can be there for Judith during Frosh Week when she has Max to babysit. But perhaps helping Judith during Frosh Week is not her ultimate goal. Both Erica and Judith learn that friendship is a two-way street. Meanwhile, Sam tells Barb that she and Josh are moving to London for Josh's work. Barb, who thinks Sam is doing this for the wrong reasons, needs to decide what to do with this information.
- Having not seen or heard from her since she left to follow a guy to Los Angeles six months ago, Erica receives a surprise visit from Jenny, who admits she made a mistake, yet again, in making that move and didn't want to face Erica in disgrace. Rather than be angry, Erica vows to help Jenny get through this rough period in her life. As 50/50 Publishing is going through growing pains, Erica convinces Julianne to hire Jenny as their assistant. Although Jenny tries in her own way, Erica ends up doing most of Jenny's job while neglecting her own. And while the work at 50/50 piles up in general, Jenny is quick to abandon the office if she feels none of that work is her responsibility. Dr. Tom and the therapy group make Erica examine her friendship with Jenny, both in discovering what is the underlying reason for them actually being friends and how she can help Jenny amend her ways so that Erica doesn't end up hurt. And if being hurt is part of the "joy" that Erica receives from this friendship, is there only so much Erica is willing to take to stay friends with Jenny. Meanwhile, Judith, who admits that she and Anthony are going through preemptive marriage counseling, runs into an old boyfriend.
- When Erica goes back with Camilla on one of her regrets, Erica inadvertently runs into Seth Newman, who is really an Orthodox Jew named Shimon Nyberg and not an-ex cult member as he writes about in The Purple Door. Erica feels helpless in this situation as Dr. Tom will not allow her to add signing Seth Newman as a regret since she gleaned his fraud through a method through which she shouldn't. And Dr. Tom feels helpless since he feels responsible for Erica finding out and can't do anything within the rules of therapy to help her. As Erica and Julianne try to figure out how to get out of a bad situation where both obvious options would cause them further problems, Dr. Tom decides that he has to do something to right what he feels is his wrong. Meanwhile, Ivan and Dave hit a bumpy path in their relationship based on secrets. Sam and Lenin face further disparities in their professional lives. And Judith and Will, both feeling somewhat dissatisfied with their respective married lives, have to figure out what to do about their mutual attraction to each other.
- Julianne and Erica have a somewhat uncomfortable time at Frank Galvin's funeral in the fact of running into some of their old nemeses, most specifically Thomas Friedkin. Julianne is also expecting a visit from her sister Georgie, a brilliant academic, who wants to pitch a book by her friend, local professor Michel Streith. Both these events place Julianne on edge, more so than usual, her frustrations which she takes out on 50/50's new assistant, Rachel. Julianne and Erica have differing opinions about Rachel, who Erica likes, despite her quirky nerdiness, which includes being somewhat psychic whenever she gets nervous, which is all the time. All these situations in combination make Erica incredulous to the announcement by Dr. Tom of her next patient: Julianne. Erica believes that strong, confident and results-oriented Julianne does not require therapy, and that Julianne's gruff demeanor only comes out when those around her don't know how to deal with her properly, much like Rachel doesn't know at this time. To test Erica's theory, Dr. Tom sends Erica back to her first day at River Rock working under Julianne. Erica believes since she now knows Julianne as a person, she can make a better impression this second time around than she did the first. But an incident shows Erica what truly makes Julianne the person that she is. Meanwhile, a confession by Rachel makes Erica contemplate her own future.
- Erica realizes that she has feelings for Adam, but won't do anything about it since she believes they are like oil and water. As such, Dr. Tom tells her to spend her day doing what her impulses or "id" tell her to do, without her conscious or "superego" censoring those decisions. This day happens to be the day of the Pride Parade when her old friend Cassidy is coming back to town. Spending the day with homosexuals, Cassidy in particular, may help Erica in this task as she has seen how Cassidy, as a homosexual woman, has taken those risks and acted on her impulses. But what will Erica do when confronted with the issue of Adam. Meanwhile, three other couples take their friendships/relationships to a new plateau, namely Julianne and Ivan, Barb and Gary, and Sam and Lenin. With the latter, Sam, on her first date with Lenin, is uncomfortable with their professional disparities, and has to figure out what to do about it.
- Beyond the shock of the news, everyone seems happy about Samantha being pregnant with Lenin's baby - everyone except for Barb. Barb believes Samantha is being irresponsible yet again. Erica is surprised by her mother's reaction, but she will have to understand that reaction after Dr. Tom tells her that her mother is her next patient. Erica thinks she knows why Barb is feeling the way she is, but Dr. Tom sends Erica back to 1969 and seventeen year old Barb's senior year in high school to get a true picture of what is bothering Barb in present day. What Erica finds out about seventeen year old Barb is something that she will have to process as it affects her personally. But she also has to figure out how to provide Barb with some guidance without divulging Barb's secret past. News of the baby brings up the baby issue between Erica and Adam for the first time as it relates to their future. And Dr. Tom runs into an old flame named Amanda Mathieson. As Tom buries himself in his work and contemplates not reconnecting with Amanda, Dr. Naadiah tries to convince him that Amanda has probably come back into his life for a reason important to him.
- In the next phase of her doctor training, Erica, for twenty-four hours, receives the power of initiating time travel. As a doctor-in-training, her current temporary powers only allow her to travel within that same day. Dr. Tom warns her that with power comes much responsibility. Erica, like a kid in a candy shop, wants to tell the whole world what she can now do. But she comes to the realization that she can fix some mistakes that she feels she's already made that day. One has to do with Julianne and Brent, who are moving into new territory in their relationship. They pitched a book idea that Erica dismissed in its entirety. But the more important regret has to do with Adam, with who she had the latest in what seems to be a continual string of fights. The nature of their fights seem to take on the same issues: Adam feels that Erica is trying to control his life - much like he is her patient - while Adam, in a state of anger and wanting to cool off, walks out in the middle of the fight. Another source of their fights is Kai, who Adam does not want her to see anymore. As Erica tries to redo that latest fight so as to diffuse the situation the second time around, she finds that in trying to fix what she did, she is also controlling the destiny of others. She also finds that the problems that she and Adam are facing may be more deep seated than what a little time travel can fix.
- By opening up a part of her own personal life to him, Dr. Naadiah is trying to show Dr. Tom that he can be a good therapist and still maintain a healthy personal life. She is trying to get him to return the several telephone calls from his former fiancée, Amanda, to see why she has come back into his life. Telephoning Amanda and forgiving her for walking out on their engagement to marry another man may be two different things. Dr. Naadiah sends Tom back to his and Amanda's engagement party, where he believed that Amanda was looking for an excuse to leave him so that she could marry who would eventually be her husband, Paul. The party isn't quite as he remembers. A current day visit with his own father may show Tom what he needs to do to make himself more fulfilled in his personal life. Meanwhile, Kai has returned from the future to deal with a regret. During what may be an extended return, Kai makes a special effort to get in touch with Erica. Because of Erica and Kai's history, a jealous Adam doesn't like that Erica wants to spend time with him. Erica thinks that Adam may change his mind if he gets a chance to hang out with Kai himself as a buddy.