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"Therapist" Dr. Tom, who is constantly spouting famous and not-so-famous historical quotes, is Erica Strange's savior and worst enemy. Erica, a young woman, is having a bad life because of the bad decisions she's made, and she provides Dr. Tom with a long list of those pivotal moments in her life that she feels have led to the bad state she is in today. She's initially unaware of what he intends to do with this list: he will transport her back in time to each of these moments so that she, with "what she knows now", can make better decisions to fix her life. Regardless of these new decisions, Dr. Tom hopes that Erica will come to the realization that although others' opinions of her life matter, what matters more is what she thinks of her life and decisions.
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Episode 1
45 mins
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.