Olive grew up in the UK (specifically Wales) on a large family ranch. Her family was very wealthy, and Olive grew up as a spoiled rich kid who wanted for nothing. Ex: She had a “playhouse” that was likely bigger than a room at the pink cage. She had private tutors (that she hated) as a child until eventually her parents sent her to a boarding school to finish her education at around eleven years old, but was very close to her childhood nanny. Her relationship with her parents was virtually non-existent. While they loved their children very much, they weren’t very attentive and tended to focus on their jobs and other priorities.
She was the middle child in her family, the only girl with two brothers. Her relationship with her older brother was rocky. They fought constantly over silly things and could be very cruel but were also very protective of each other. To her younger brother, Olive often felt like a mother. She felt responsible for him and was quick to speak for him when anyone asked him anything or wanted anything from him. She did her best to protect him, if she felt like he needed it. And since he was a pretty quiet kid compared to how loud she and her older brother could get, she often felt like he needed it.
Olive got a reality check when she was sent to boarding school. Being homeschooled as a child and having her brothers as her only friends left her with little to no social skills. She was quick-tempered, too, which meant that she was easily messed with. She spent most of her time being bullied and feeling virtually friendless. Olive hid a lot of her torment from her older brother (who attended the same boarding school), but would often confide in a boy whom she had a crush on.
When Olive finally got around to confessing her feelings for the boy (around age 15), she was told that they couldn’t be together. The boy (who flirted with many girls around the school) told her that he didn’t believe in monogamy. He told her that he thought love belonged to everyone and tying himself down didn’t seem fair. Olive accepted this. She knew that the boy was seeing other people, but she craved the moments that they could spend together and never sought out anyone else for a relationship. She was often left pining.
Her biggest disappointment during her younger years was when her younger brother decided to attend a different school than the boarding school her family had been going to for years. She had been looking forward to his attending so that she could have at least one person around that she felt genuinely close to, but he opted out. It hurt Olive very much and created a wedge in their relationship.
After her graduation, she left on a trip to see the world (as encouraged by her parents), but never returned home. Having always felt like the black sheep back home and at school, Olive took the opportunity to run away for good.
Coming to Los Santos Edit
Olive entered Los Santos at 20-years-old (two years after she ran away from home), and at this point had run completely out of money. She was homeless and had no real skills in order to find a job. She made an attempt to make money by first driving a taxi, but after totalling her taxi during her first shift, it quickly became apparent that it wasn’t the job for her.
In desperation, she reached out on twitter for career help and a towing/mechanic company reached out to her. Olive attempted to explain that she had no knowledge of cars, but they promised her that they would offer on the job training. Olive spent several weeks doing towing ride alongs with Charlie Johnson to learn how to tow, and once she got the hang of that, she was taught to repair cars by both Charlie and Denzel Williams.
Olive answered to many people at the mechanic shop, StarShafters. Her bosses and owners of the shop were Denzel Williams, Tidus Martell, and Andre Adonis. Gradually over time, she learned that the three were underbosses to a gang, and they introduced her to many of their associates - including a man named Briggs who she was told would be around to act as security for the shop if things got rough.
It wasn’t long before she started to casually date Briggs and along with that came certain responsibilities related to the gang. She became privy to more information and would often have to use her mechanic job to gather intel about people around the city. She would collect the make, model, and license plate of everyone’s cars to pass along. She would listen to conversations people had with their friends while waiting for repairs and often found out information regarding their illegal activities in this way. And would even strike up conversations with her customers to learn more about them (typically their friends, business, and homes).
Her relationship with Briggs also brought up other problems for the group. They didn’t completely trust her with the information she was getting from them and often brought up to Briggs their desire to kill her to clean up that loose end (especially since Olive was friendly with many police officers around the city). When it became clear that Olive was dating other people alongside Briggs, their trust for her dropped even more. One man she dated was a man who ran tow for the shop named Paul. The group found him sketchy and often worried that he was an undercover cop, or a CI, trying to figure out their dealings to turn them in.
Her on-going casual relationships caused her relationship with Briggs to become tense and volatile. Despite his refusal to say so, he wanted her to make a solid decision about who she wanted to be with. Olive was very uncomfortable with this because she’d come to believe that no one truly enjoyed monogamy and didn’t have the self-esteem to believe that someone would want to fully be with her. It wasn’t until one day, when Paul talked out Olive’s feelings with her, that she finally decided to drop everything else and commit herself to Briggs.
With their relationship finally cemented into place, the gang decided to blood Olive in as a sort of last-ditch effort to make sure she would never turn on them (despite the fact that Briggs was completely and openly against this). At this point, Olive started to get deeper in but always made sure to keep a certain distance from what was going on. She never wanted to be put in a position where she might end up in prison but agreed to do other things to help the gang - such as holding a property for them to use as storage and even help Briggs (and Charlie) sell drugs when they needed the lookout.
As time went on, Briggs was given more power in the group (Olive encouraged him to take up a position as an underboss when it was offered to him), and as they became more aware of the internal arguments and power struggles in the group, they began to pull away. Briggs began to funnel money out of the gang - often lying about how much he was making and what exactly he was getting out of the people who worked under him. Olive was also given more power at the shop (becoming promoted to manager) and was free to run it as she saw fit - with the owners showing up less and less to keep order at the shop.
When they had amassed enough money between them (millions of dollars that had been funneled out and into their bank accounts), Olive and Briggs decided to get out of the city. On their last day, Briggs proposed to Olive and, despite her continued reservations about long-term monogamy, she accepted. They then left Los Santos to travel the world together.
Returning to Los Santos Edit
Months after they left the city, Olive begins to feel paranoid that they’re being followed. As her paranoia mounts, she makes the decision to leave her now-husband Briggs at their hotel in France and return where she knows she could easily disappear: Los Santos.
During her first week in the city, Olive seeks out a therapist and opens up about how she thinks her family might have seen them in Europe and might have recognized her. She’s worried that they’ve hired a private investigator to follow her to figure out if she really is their long lost daughter. The therapist suggests that Olive might be feeling paranoia to hide her guilt of moving on and getting married without her family there. The therapist suggest that she personally reach out to her family and reconcile with them, but Olive says that it’s not possible. Her family believes she’s dead, and she thinks it’s best that they continue to believe that - for her to remain a ghost.
A little over a week after she returns to the city, Briggs arrives and with the help of one of his old lackeys, they track down Olive. Briggs angrily confronts her about how she abandoned him overseas and about how she broke the promise to him where she swore she would never leave him behind. Olive claims that the promise wasn’t broken - that she had only sworn to never leave him behind in Los Santos. This technicality angers Briggs even more, who was expecting an apology, and their tension mounts.
When Olive finally explains why she left, Briggs becomes paranoid for his own reasons. He states that he’s worried that it’s the old gang who managed to track them down overseas, and now that they’ve returned to Los Santos, the gang might show up and attempt to kill them for stealing the money and disappearing without a trace. Olive claims to have not thought of that, and then breaks the news that all of the money and their vehicles that they had left behind in Los Santos in case of an emergency is gone. She also breaks the news that she’s been unable to access their other accounts outside of the city and that they’re broke and can’t get a plane ticket back out.
Olive takes it upon herself to stay in the shadows in order to gain more information about who’s been following them, and Briggs soon goes to work to try and make money so that they can leave again. Briggs goes around the city to offer private security to anyone who needs it, and as he struggles to find work, tension between him and Olive continue to build. They argue about money constantly, and Briggs begins to show bitterness towards Olive for getting them into that mess. At their worst point, Briggs accuses Olive of not caring about their relationship as much as he does and his prime example is the pressure he feels to make them money to get out of the city. Because of this argument, Olive decides to take the L and do what she never wanted to do: Get back behind the wheel of a tow truck.
Filled with fear that Briggs will soon want to leave her, Olive tries her best to be a better wife. She tries to be more understanding and attempts to stop picking fights with him. Olive even goes so far as to go out of her comfort zone and do more domestic things (such as ironing Briggs’ suits for him) to show that she cares.
Briggs took on a job as security at the car dealership and quickly began making other connections around the city. As he started to meet people, Briggs quickly became friends with a gang leader named Jose and became his secret criminal advisor and confidant in exchange for protection for him and Olive. Over time, Briggs found and met up with several members of the old gang and found that many of them had moved on and held no grudges against them for their past decisions. So with Briggs’ worries thrown away, this left Olive feeling like she had even more reason to believe her family was searching for her.
At this point several months had passed, and with Briggs’ job security at the car dealership, they had managed to make enough money to leave. After a lot of struggles and hard decisions, Olive decided she was right in her original opinion: She did not want to stir up trouble by having her family find out she was still alive. With a lot of evidence (and people) left behind who could bare witness to their presence and life in the city, Olive and Briggs decided to leave again in the hopes that her family would continue to chase leads left behind by them in Los Santos until long after their trail ran cold.