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Erica is talking to Dr. Tom when he gets a call from Amanda. He interrupts the sesson, but after Erica leaves, he disconnects the call. Dr. Naadiah comes in, asking why he has hung up on two of Amanda's calls, and where is his personal life on his list of priorities? He says: I invest in my patients, show me a therapist who has a "real life". Dr. Naadiah says alright, and he finds himself at her home at a vibrant backyard party.

Tom meets Dr. Naadiah's family and says to her: you have a wife, child, dog, and a job as doctor. How do you do it? She says she makes her life a priority, whereas he doesn't and he makes excuses. She tells him to take a risk. Tom finally returns Amanda's call.

Dr. Tom and Amanda are taking a stroll and catching up. She assumed he traded stocks and was rich, and is surprised when he tells her he's a therapist. Her comment: wow, same on outside, but on the inside: a big mystery. That's the man I remember.

Erica is editing Ivan's speech at Goblins, and discloses that things with Adam are amazing, but they've been having arguments lately (like earlier when she heard Kai on the radio and Adam wasn't impressed). She asks if she's overreacting and Ivan says no, you've moved on to phase 2, the "eclipse". He tells her the honeymoon is over, it's all downhill from there, but if it's meant to be, they'll pull through and move on to phase 3: commitment. Kai shows up at Goblins and tells Erica he's back on a regret: avoiding the sophomore slump, and redoing his second album.

Back at Amanda's, Amanda asks Dr. Tom why it took so long to call, and he says he doesn't know. They argue about the past and Dr. Tom says it's late, leaves, and ends up in his office with Dr. Naadiah. He tells her: tonight was a mistake and she asks: why? Dr. Tom thought he was over the fact that they were engaged, and Amanda left him for someone named Paul. With prompting from Dr. Naadiah, Dr. Tom thought it started at their engagement party, where they had an argument over a trip. He wanted to postpone the trip since he had gotten a significant promotion; she refused to cancel the trip, and ended up going without him. He then received a postcard from her, telling him it was over. Dr. Tom thought Amanda had never loved him, and used the trip as an excuse to leave him. Dr. Naadiah's response: "History is shaped by the one doing the telling. The only way to know is to go see for ourselves."

At the engagement party, Amanda is giving a speech, saying how happy she is, and that they'll be going on a world adventure tour. Dr. Tom's father looks annoyed, and later confronts Dr. Tom about not telling Amanda about his new job and promotion. The father said they were both young, and that Dr. Tom should be focused on his career as managing director. Dr. Tom asked his father when his mother left, did he see that coming? He revealed his concern that he loved Amanda but wasn't sure she felt the same. His father said: "you can never be sure, I learned that the hard way with your mother. Marriage is a crap shoot. Your career is all you. Adventure is fun, but invest in things that will yield a return. Your work, your future." He urged Dr. Tom to tell Amanda about the new job.

Erica comes home and tells Adam she ran into Kai at Goblins, and that he is back on a regret. Adam is defensive about this, but Erica thinks if they met over drinks everything would be fine, the way Adam is friends with Darryl and they meet for drinks. Adam says that's different, that's fine with a random guy but Kai and Erica have history.

Back at the engagement party, Dr. Tom finds Dr. Naadiah tending the bar and asks if this is some sort of alternate reality, and that Amanda seems to truly love him. Yet by next year, she's married to Paul. Dr. Naadiah affirms this is indeed how his past unfolded.

Dr. Tom is pacing outside, when Amanda and Paul return. Dr. Tom is suspicious about this, and then finally tells her he's accepted a managing director position which starts in two weeks. Amanda is upset that he made up his mind without consulting her. Dr. Tom tries to convince her they could travel anytime. She responds that he can't put their relationship ahead of his job, and that she is going on the trip. Dr. Tom retorts that she can meet up with Paul when she gets there. That's when he learns Amanda and Paul had gone to get scotch for Dr. Tom, since Amanda didn't know about the different types of scotch.

She asks Dr. Tom why he would be suspicious of her and Paul. He admits he's not sure she wants to marry him and she assures him she's sure, but if he's having doubts they should talk. When he's unable to talk about his feelings she asks why he always turns things around when he doesn't want to answer a question, he gets mad or changes the subject.

He returns to present and tells Dr. Naadiah: "Amanda didn't abandon me. I abandoned her. I put my job before her, just like with Marjorie, Sarah, same pattern my whole life." Dr. Tom then added a regret, to go back and see what would have happened if he had turned down the job and gone on that trip with Amanda.

When he returns to the past, Amanda is packing, moving back with her parents, and calling a lawyer on Monday. When he wants to know what he's not doing right, she tells him: "I know you love me, that's why I stayed as long as I did. But when things get difficult you go away, you shut me out. When I ask you why you say I don't know." 

Back in the present Dr. Tom tells Dr. Naadiah this was a waste of time, that he knows he pushes everyone away and needs to work on that, and that he started to with Sarah. He says his patients are satisfied and Dr. Naadiah agrees and says: "you're an excellent doctor, but patients are no replacement for a real life... Work is a symptom, it's what you use to hide. Now we're talking about the disease." Dr. Tom retorts that his father was the same way, and his father and he were happy. Dr. Naadiah responds that he was wrong about Amanda, so how did he know he was right about his father?

Erica, Adam, and Kai are talking over drinks. Someone tries to pick up Kai, and he turns her down. Adam is surprised. Kai said she was not his type, and that they didn't really want him, they wanted the fantasy. He told Adam: You're the lucky one.

Tom goes to visit his father and they talk during a game of chess. His father tells him not to work too hard and Dr. Tom laughs and says: this from the man who never stopped working? He is surprised to discover his father is not happy. His father asks: Who's actually happy in this world? He admitted he made his bed but it was not the best choice. When Dr. Tom asked about his advice to be a lone wolf and master of destiny, his father replied: "what a bunch of bulls---... Loneliness is a terrible thing. I do my best to stay busy but as I age, there's part of me that wishes I invested more in your mother and less in this. I put so much value on freedom, privacy, work, routines, now I'm old... And this visit will be the highlight of my week."

Tom stops at Amanda's and acknowledges that she once said she wanted to see the real him, but he couldn't let her in and still can't because he doesn't know how. That he designed his life so he doesn't have to take risks, and lives vicariously through others. He realizes he's afraid people will leave. His mother left when he was young and he doesn't want to be left again.

Erica comes home and thanks Adam for having drinks with Kai. Adam acknowledges Kai is alright but they can't be friends since Kai isn't over Erica. He tells Erica he doesn't want her to see Kai anymore.

Erica's voiceover as Amanda and Dr. Tom are kissing and she leads him to her bedroom: "They say that without risk there is no reward. But perhaps it goes further. Without risk there is no exploration, no discovery, no delight. So don't waste time. Take a risk. See what comes."

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