Olivia and Fitz first meet during Fitz's campaign tour to be the presidential nominee for the Republican party. He was trailing behind Sally Langston after their visit to Iowa and Cyrus Beene brings in Olivia to do what she does best, fix things. When Fitz asks the question on why they are trailing behind, Olivia stands up and tells him it's because it looks like he doesn't have a happy marriage and people want to like the family. Not knowing what to do about Olivia, Fitz goes to Cyrus and tells him to fire Olivia, not realizing that Olivia overhears the whole conversation. Cyrus tells Fitz if he is really set on becoming president and have Cyrus represent him that he should find a way to keep Olivia. As Olivia leaves, he apologizes for firing her, and when she asks him why he tried to fire her, he is at a loss for words but it’s obvious it’s because he has feelings for her. Olivia lets Fitz and Mellie know that the only way they have a shot at the White House is if they start acting like a real lovey-dovey couple. So, after a yelling match, they begin doing just that.
As they travel across the country, they get to know about one another, getting closer to each other. When at the republican presidential debate in North Carolina, Fitz is asked about his marriage and he says “The most honest thing that I can tell you about myself right now is that I am a man in love with an incredible woman” and he finishes it off by looking straight at Olivia. Later, while in an elevator, Fitz tries to make a pass at Olivia (she sees it, but doesn’t want to stop it) but right as they are about to kiss the elevator door opens. The next day, while preparing for Super Tuesday, Fitz pulls Olivia out comes up with excuses about why it would be wrong for them to be together but he changes his mind, telling Olivia to just there with him for one minute and to just forget about everything. As they lean in, to kiss, the door opens, and Mellie interrupts, giving Fitz the stink eye. Fitz stays in the hallway, trying to think things through.
After visiting Georgia and listening to Mellie tell about her miscarriage, Olivia still awake on the campaign bus (let be honest she never sleeps) goes to the back of the bus to talk to Fitz. She apologizes for the miscarriage, only to have Fitz tell her, Mellie lied about the whole thing. He tells her that he is a coward because he couldn’t wait for love and to have gotten married in a rush for power. When she calls him Governor Grant, he tells her to be inappropriate and call him Fitz. She finally gives up the formal side of herself and they hold hands. When they get to the hotel, she decides that she doesn’t want to go to her room, and goes to Fitz’s room. Where they make love, not knowing the room is bugged and recording everything.
In the first episode, when Amanda Tanner first starts the accusation that she has slept with Fitz, Olivia's gut tells her that she is telling the truth but decides to believe Fitz because he tells her that he loves her and not Amanda. When she finally has enough proof to trust her gut she goes to confront Fitz, where he tells her that it only happened because she left The White House. He then grabs her and they start kissing, when Cyrus walks in and discovers their relationship. Leaving Olivia shocked because she was under the impression that Cyrus knew about their relationship. She then tells Cyrus that Fitz better be careful because Amanda tanner is her new client. "(Sweet Baby)"
In the second episode, Cyrus tells Fitz that the relationship is over and it needs to stop. He then has Olivia taken off the cleared list to enter The White House without telling Fitz. When Olivia finally gets in to The White House, Fitz tries to get her attention, but she leaves before he can get to her. When Fitz finds out that Liv has been blocked, he tells Cyrus that he doesn't need protection. When Liv returns to tell Stacy Keating that she has to tell her husband, Patrick Keating, (supreme court justice nominee) who she is, Fitz finds a way to talk to her. Fitz begins to tell her about how he thinks love is and asks Liv to forgive him for sleeping with Amanda Tanner. Liv pulls away saying there is nothing left to be said. Later, while a little bit drunk, Fitz tells Cyrus that Olivia is the love of his life and that she has stopped talking to him. "(Dirty Little Secrets)"
In episode three, Mellie Grant cancels Fitz's morning appointments so that he can sleep in since he hasn't been able to sleep for days. When Mellie asks why he is not sleeping (she is well aware that it is because of Olivia) he doesn't respond and Mellie tells him that she just wants him to have what he needs, he stands there stunned. When Amanda asks that Liv make an appointment for her to see the president, she goes to Cyrus to ask for it, clearly because she still doesn't want to see Fitz. When Cyrus tells her that Fitz isn't sleeping, she says that it's not her problem and that she isn't sleeping either. She then tells him that if Fitz can agree to a sit down with Amanda, the whole thing will be over. When Cyrus tells Fitz about the meeting with Amanda, all he cares about is whether or not Liv will be there. Later in the day, Cyrus gets an audio tape of what seems to be Amanda and Fitz having sex. Cyrus insists that they shouldn't go in for the meeting because Amanda is black mailing him (which in turn means that Liv is too). Fitz insists that Olivia is not blackmailing him and to keep the meeting. Mellie takes it upon herself to invite Liv to the state dinner so Fitz can see her and maybe get some sleep. At the dinner, Fitz tells Liv that he only loves her and to meet at their "spot". On her way there, Cyrus stops her and tells her that black mail is not okay, that Fitz was playing her, "the meeting" (with Amanda) is off and that she must leave immediately. Later on, Cyrus finds Fitz at the "spot" and tell him that Liv left and cancelled "the meeting". "(Hell Hath No Fury)"
In episode four, Olivia goes to tell Cyrus that Fitz is in a lot of trouble because Amanda is pregnant. When Fitz asks how things are on the Olivia front, Cyrus tells him there is nothing he can't handle. Cyrus finally gives Fitz the speech of what will happen when Amanda Tanner tells the public about the affair. It makes Fitz think that maybe he can finally have the life that he wants with Olivia. Fitz finally decides what he wants and finally gives Cyrus permission to go to war with Olivia. "(Enemy of the State)"
In episode five, Amanda Tanner's death sends Olivia over the edge. When Fitz calls, she tells him that Amanda is dead and that it's his fault, but he denies that he had any involvement. Olivia tells him that if he didn't, then Cyrus did, which is Fitz's fault. After Fitz receives another message of black mail, proving that it isn't Olivia who sent the audio tape, he decides to pay her a visit. "(Crash and Burn)"
The sixth episode begins with Fitz at Olivia's house talking about the death of Amanda Tanner and his non-involvement. He asks her to listen to the sex tape, where it revealed to her that the sex tape is not of Fitz and Amanda, rather Olivia and Fitz from when they were on the campaign trail. They spend the night together, and before Fitz returns to the white house they once again spend one minute thinking about nothing. "(The Trail)"
When Cyrus gets to work, he gets angry at Fitz for spending the night at Olivia’s house. Fitz claims that Cyrus is only angry because he couldn't stop his mentee from falling in love with Fitz. When Billy Chambers comes out and tells the public about the president’s affair with Amanda Tanner, Olivia comes to the rescue to save the president’s image and reputation. As the media picks up the story, it seems more and more likely that Fitz will have to resign as President. When Olivia and Fitz are left alone after Cyrus throws a temper tantrum, she apologies for not being able to fix the problem, but Fitz tells her not to be because if he resigns they can finally be together. They both have a realization that they can finally have each other and they kiss. Olivia leaves the oval office excited for what may be ahead for her and Fitz only to be stopped by Cyrus. Cyrus tells her that he doesn’t doubt that Fitz would be happy as a "normal" man but rather he was made to be great, not happy. The speech convinces Olivia that it would be selfish to keep Fitz for herself. She finally decides to go see Mellie to find a way to resolve the issue because she knows that Mellie is willing to lie. When Mellie sees Olivia, she tells Olivia that Olivia is the one to blame because she left The White House which broke Fitz's heart leaving him vulnerable to Amanda Tanner and Billy Chamber's ploy. Mellie proposes the deal that she gets to keep Fitz because she believes that Olivia is no longer capable of looking after the President, and in return Mellie will say that she was the one on the tape and that she pregnant. When Fitz arrives to hear about the plan, he is heartbroken because he believed that Olivia was on board with the plan of him resigning from his presidency, it breaks his heart more when he realizes that he will have to get Mellie pregnant and that the idea came from Olivia. When the interview is about to start to clear up the affair story, it is clear the relationship has take a harsh turn. When Olivia leaves, she returns her access badge back to Morris Elcott at the gate. "(Grant: For the People)"
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