Starting in the darker red 'Present Day' circle, the timeline of the episodes and the season is mapped out below. Lindsay follows this path to go through different times and experience first-hand different famous romances of history, finding flaws in each that, similar to in the pilot, she attempts to micro-manage and 'fix', vicariously living through the players and projecting issues of her own failed relationship.

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As she progresses through each time, Lindsay learns more about love and what different shapes it can present as. Each time and romantic partnership is related to coursework or hobbies she has from her own time, so she holds a good amount of knowledge and understanding for all she encounters.

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In order, she will encounter the following relationships:

Episodes 1 and 2 -- Romeo and Joyce ('Juliet')

• Lindsay tries to save the two star-crossed lovers from their gruesome fate.

Episodes 3 and 4 -- Aaron Burr and Theodosia

• Lindsay watches and meddles in the homewrecking situation of Aaron Burr seeing a married woman

• At the same time, she finds Colin again, in this time named Seth, though now he is also dating someone. She thinks Seth and his woman aren’t good for one another, seeing his former ex in her, and she tries to split them up. This ends up working well for her. 

• In episode four, Lindsay finds that things additionally escalate when her attempts to set Burr and Theodosia start to go poorly.

• Lindsay also has a flashback to how a girl once tried to home-wreck her and Colin, and as she does the same to Seth and his lover, not making the connection until she’s perhaps ruined someone who isn’t technically hers.

Episode 5 -- Queen Victoria and Prince Albert​

• In a stand alone episode for a single time period, Lindsay shows up in 1861 England in the court of Queen Victoria after the passing of Prince Albert. Queen Victoria is devastated, and Lindsay helps her take her mind off her late husband by focusing on new love--that of Princess Alice and Duke Louis.

• At the same time, Lindsay again finds Colin, this time a servant boy named Andrew, and though she keeps finding herself in presence, afraid to make the same mistake twice, Lindsay tries to avoid Andrew, but they end up making nice and being friends at the end of the day.

Episode 6 -- Robert Frost and Elinor Miriam White

• It’s 1894 New York City. Lindsay tries to figure out why she hasn’t woken up and returned home yet, but ends up wandering into a new love story, this one of Robert Frost and Elinor Miriam White.

• Frost is rejected at his first proposal, though Lindsay is more just excited to meet such a great poet and figure of history. He asks for advice from her, but she is wary of meddling now and instead writes a lot of poetry with him that ends up helping him.

• Frost introduces Lindsay to another friend of his that’s good with words, a shopkeeper named Joseph, aka Colin again. Lindsay understands she cannot escape him. He finds her attractive and asks her out. She accepts, though the date brings up trouble when he’s not the man she knew him to be from having dated him in her own timeline.

Episode 7 -- Ernest Hemingway and Hadley Richardson/Pauline Pfeiffer

• Ernest Hemingway married 4 times in his life. Lindsay is there for the transition between the first and second.

• Another stand alone episode--this one 1926. Lindsay is so excited to meet Ernest Hemingway, another poet she looks up to, but she’s quick to lose respect when she realizes he cheated on his first wife, Hadley Richardson, and the two are going through a divorce after which Hemingway immediately marries another woman.

• Lindsay, drawn to Ernest (played by William) wants to sympathize or at least understand his side of the story, but she’s quick to realize how wrong he is, and she stands with Hadley.

• This is intercut with a B plot of flashbacks from a relationship Lindsay was in before Colin where she was cheated on. This will have been mentioned in episode 2, but she won’t admit to details until now

Episodes 8 and 9 -- JFK and Marilyn Monroe

• 1962 New York City. Marilyn Monroe sang ‘Happy Birthday Mr. President’ to JFK, and rumors start going around that they’re having an affair. Having just come from the Hadley Richardson situation, Lindsay is ready to hold Jackie’s hand through a divorce, but instead, Jackie talks to Lindsay about her plans to stay with him. The two clash in some thinking about what straying and cheating looks like. They have very opposing views.

• Lindsay spirals and meets Colin, this time Sam, an intern at the white house, and finds that he too has a wife, but in her spiral, she lets Jackie get in her head and completes the deed she wasn’t ready to complete earlier on in the season and becomes the other woman.

• In the ninth episode, Lindsay feels ashamed of what she’s done. She talks to Sam about any future they might have together, but as it turns out, even if she were to stay in this timeline, he wouldn’t be hers to keep. Which she knew. She just didn’t want to admit it. Lost, she confronts Jackie to find out that Jackie is pregnant. Jackie talks about how she has to hold this family together for the country no matter what JFK might do in her absence. Lindsay feels bad for her. She says her goodbyes to Sam.

Episodes 10 and 11 -- Amy Winehouse and Reg Traviss

• 2010 -- London, England. Lindsay is tired and just wants to go home. She thinks about the possibility of staying in 2010, but this is a decade she doesn’t really want to go through again.

• She finds herself at a concert and meets and is dragged into the final year of the life of Amy Winehouse. She just cleared up a divorce of her own and is now involved in Reg Traviss. The two have their whirlwind romance.

• Lindsay is brought on as a roadie alongside Colin--in this timeline named Daniel. She shuts down his advances and tell him they’re better off as friends. One night they get drunk and have a moment, but again she escapes, telling him she has a boyfriend from the states, Colin. Caught in the lie, she tries to get out, but not before spending some time with Amy and learning the life-is-short-go-get-him lesson. She ends up not being able to follow through with it though. She can’t keep doing this to herself with this boy.

• There are rumors that Amy Winehouse might be pregnant, and after becoming so close to her, Lindsay decides to meddle one last time and try to save Amy from dying. She tries to get her clean of drugs, but Amy doesn’t accept it.

• She also has an important conversation with Daniel talking about their ideal futures. It turns out, they have very different ideas of what that might look like. Perhaps it’s for the best they don’t stay together long term.

Episode 12 -- The Full Circle

• Lindsay is shot back to 1517 Italy. Confused and frustrated, she thought she was about to get back to her time, but has now lost so much ground. She thinks she did something wrong and has to reevaluate, but as it turns out, she ended up here for a reason, and she meets Da Vinci. The two have a long conversation about what she learned across times, how she tried to meddle and fix things, how nothing ever worked. He tells her the next time she finds herself sometime new, perhaps she just needs to watch.

• She’s then transported to 2017. At first, thinking she made it back, she celebrates, but then she realizes when she is. She watches herself and Colin meet for the first time alongside a homeless man, The Drunkard/Drifter. He knows her name and tells her not to meddle. She watches and cries. This was the beginning of what ended so tragically who knows how long ago now.

• Then, she’s back in 2019. She stands across the street from her house, and she watches herself get out of Colin’s car and run inside. She watches him drive away. She walks up to her own door and knocks, then opens it on herself, knocking herself out and sending herself back in time.

• There’s another knock at the door. She doesn’t answer at first, thinking she might send herself back again, but after hearing a voice behind it, she opens it to find Joyce. Joyce introduces herself as Nicole. She’s here to talk to Lindsay about subleasing the upstairs bedroom. Lindsay tells her she thinks they’re going to be great friends.

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