Olivia met Jake in a pastry shop ten months after the death of Verna Thornton and their relationship has been on and off ever since.
Their relationship actually started as Fitz asked Jake to keep Olivia safe through the video surveillance. Jake slowly developed personal feelings for Olivia while watching her so, he planned to meet her. Later Jake met Olivia in a pastry shop as they were standing in line and Jake knocked Olivia's phone out of her hand while she was using it. Jake picked it up, they flirted a little and then Jake left the shop. Then later that very day, Olivia went looking for Captain Jacob Ballard in the pentagon where he worked because of one of her clients, they met again and this time, Jake asked Olivia out for a dinner. Olivia firstly turned down his offer probably because of Fitz and then leaved. When Fitz said to Olivia that they're done because of her betrayal to him with Defiance, Olivia came back home and called Jake that she'll go out with him and finally, they went out on a date. Things sparked up quickly between them but after Olivia found out about that Jake's been watching/stalking her, she refused to see him again.
However, after Jake saved her from getting shot in her own apartment by a B613 agent, she realized that Jake has saved her life twice and she told Jake that she was wrong about calling him the bad guy when actually, he is not. She then found out that Jake is also a B613 agent and now B613 people will try to kill Jake because he saved her life by disobeying an order. She kissed him goodbye gently and then Jake leaved her office because it would be safer for Olivia if he is not with her. It was later shown that Jake's been thrown into the hole because he disobeyed an order from Command of B613 by saving Olivia's life.
Jake was released from "the hole" later because Olivia made a promise to her father Command that she will have Sunday dinner with him again which she stopped going to when she found out that her father runs an organization which trains people how to kill.
Jake and Olivia became closer in season three after Jake was released from "the hole" because of her. Their relationship developed into something where they feel comfortable telling each other things and understand each other. Jake made a promise to Olivia that she isn't alone and that he's not going anywhere and assures her that he loves her no matter what happens next. When Jake became Command in the last half episodes of the season, Jake had to kill James because he was spreading the truth about Sally Langston murdering her husband. When Olivia knew about this, she told Jake that they can't be together now that Jake killed James whom Olivia considered her friend. Later, Olivia decided to take down B613 and slept with Jake to get the Intel of B613 since he was the command. Although it was all about getting the information from Jake, Olivia admitted to Jake that she felt something with him that night but then she felt guilty about it because she loves Fitz.
Jake told Olivia to save him from this terrible situation where he has to made decisions about killing people off and to run away with him. First, Olivia said she can't do it, she can't save him but then later when she found out that Fitz won the election for his second term because her father Rowan killed Jerry Grant Jr. , and that her mother is actually a terrorist who blew up churches that killed many innocent people, she decided to run away to somewhere other than Washington, D.C. At first, she was going to go alone because she is the reason that every horrible things that has happened happened and that she is the thing that needs to be fixed but when Jake asked her again to save him and to run away with him, she decided to do it. She decided to "stand in the sun" (which is their catchphrase of doing good things/right things and saving themselves from the dark sides) with him and then, they went off to somewhere together.
It was later revealed in season four that they went to a secluded island which is like a 100 miles off the coast of Zanzibar and been living there for two months. They went back to Washington to plan the funeral for Harrison when she got a letter from Quinn that they found Harrison's dead body.
After the funeral, Olivia refused to go back to the island because if Harrison was alive, he would tell her that running off doesn't make her a gladiator so they stayed. They opened up to each other more and even considered each other boyfriend and girlfriend. Things between them were good until Rowen set Jake up and framed him for the murder of Jerry Grant Jr. and Harrison Wright. Olivia didn't believe any of this and she did her best to prove Fitz that he's wrong for thrusting her father and fframing Jake.
After Olivia proved to Fitz that Jake is actually innocent, he was released. Jake told to Olivia he is surprised that she is willing to help him get out even though she can keep him in the bunker, turn her back and that she and Fitz can dance off into the sun. She then told Jake not to mention about her, the sun and another man ever again and that "the sun" is just for them. Jake then got out of the bunker by going against Rowan, B613 and that angered Rowan. An episode later, Olivia told Jake that she doesn't care about Rowan anymore now that he's gone and they danced. While dancing, she told that she wants both "Vermont" with Fitz and "The Sun" with Jake so, she's not choosing Jake or Fitz and that she chose her. Jake kissed her, they made out and when Jake went to the bedroom to get stuff, Olivia was kidnapped. When she was released from being kidnapped, she said to Cyrus that she didn't want to see or hear about Jake or Fitz anymore because she considered them as "her past", she now had to move forward and she tried moving forward by going to the bar, meeting with Russell and then having sexual relationship with him until he stabbed Jake to almost dead in her firm as Rowan asked him to kill Jake as a warning to Olivia not to do anything against him. When Jake recovered, they tried taking down the B613 again together and putting Rowan in prison.
When it was successful, they went back to Olivia's apartment to celebrate it but Jake refused to go into the apartment and told Olivia that his mission of keeping her safe is complete now that Command is in jail and it's been his pleasure. Olivia confused about why he's acting strange and then, he told her about how he's in love with her and how she's in love with Fitz and not him so, he let her go and told her that she's owed to herself to get what she wants, which is Fitz and then he leaved.
They stayed as friends as Olivia was with Fitz and Jake was with Elise. When things didn't work out well with Fitz, Olivia left him. For Jake, Elise is now dead because Olivia freed Rowan and Rowan killed her. The two of them were at odds because of the whole "Olivia freed Rowan" situation.
But six months after Olivia broke up with Fitz, they hooked up again and the two seemed to have a "just physical" sexual relationship since then. But in later episodes, when Jake got engaged to Vanessa and was about to get married, he told and explained Olivia that he doesn't really love Vanessa and that he is only doing it because of her father Rowan. He also confessed to Olivia that he still loves her although she's never chosen him and that he will never love anyone as much as he loves her. Olivia said that he can't married Vanessa and went upstairs to her room. Later, after she did some thinking about everything that Jake had just said, she came out of her room and saw Jake standing there in the hallway. When Jake went in to kiss her, she kissed him back and they then shared a passionate kiss and headed into her room. In the morning, they were smiling at each other, holding hands and then have breakfast. Later in her room, Olivia was packing things when Jake came in to tell her that he doesn't want to marry Vanessa and that he wants to be with her. When Jake asked if she wants to be with him, Olivia rushed into him and kissed him which clearly meant that she wants to be with him too. They then planned to be together but unfortunately, Papa Pope knew about their plan and told Olivia at Jake's wedding that if Jake didn't marry Vanessa, he will kill Jake and that the wedding will turn into a funeral. Olivia then had to say all the cruel words to Jake to break his heart because if she didn't, Rowan will kill Jake. She wished Jake good luck in becoming the Vice President and left the wedding all upset and shaky.
Later episodes, Jake made Edison deliver the message to Olivia about how he needs her help, how he wants to escape from Rowan and that he is chasing the sun. Olivia then saved Jake by making him the Vice President in Mellie's ticket but Jake didn't want to. He'd rather flip patties at Gettysburger and live a normal life than to be the Vice President. After Olivia said to him that mediocrity is not an option for her and that she doesn't want to live just a normal life, he mistaken Olivia that she didn't save him because he asked her to she saved him because she just wanted to save her ticket. They then had a fight and both were at odds.
Olivia and Jake stayed at odds until Olivia explained to Jake that she didn't just want to win the election, she had to win because of all the things happened in Defiance because of her decision, she needs to redeemed herself for that. Also because there has to be a reason or a point for why she did this to herself or to him.
Although Olivia and Jake didn't get back together because he's married to Vanessa, they are in good terms again. Jake would help Olivia in situations where she needs his help. When Huck went missing, they worked together and eventually found him. When Peus threatened Olivia about killing Jake if he doesn't resign from Vice President, she made him resign although he refused not to. Eventually, he resigned.
In later episodes, when Jake found out that Olivia briefly got back with Fitz, he told Olivia that Fitz is not the answer and that doing the same thing over and over again which is getting back together with Fitz and eventually not working out, it was insanity of her. They argued about it but after all, he still helped Olivia through situations where she needed his help. On the day of Mellie's inauguration, Jake came and picked up Olivia at her apartment for the inaugural ball. They went to Luna's office instead to force her to kill herself. Olivia then reconstituted B613 with the help of Jake and will run it by herself.
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