Olivia Gilbert had been sent away to a boarding school when she was just fourteen due to numerous arrests for underage drinking. With the death of parents she comes back to Mystic Falls. She has changed, her twin sister, Elena, notices. Gone is the...
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Olivia Gilbert always harbored a little bit of resentment towards her parents for shipping her off to Linsly School in Wheeling, West Virginia when she was just fourteen-years-old.
What was her parents' reasoning for sending her away?
It was because Olivia turned into a bit of an alcoholic when she was fourteen-years-old. She couldn't help the alcoholism. She and her best friend, Caroline, were thirteen when they started drinking wine coolers. It just dived into Olivia drinking more and more. Then it turned into her getting in trouble with Liz Forbes for underage drinking and getting put in the drunk tank.
According to Caroline, Liz was relieved when Olivia got sent away, because the 'bad influence' was far away from Caroline as possible. It didn't help that Caroline was the one who got Olivia into partying.
For some reason, Olivia's parents had thought it would be best to send her to Linsly to make it seem like they did something with their 'Town Drunk' of a daughter. So, she was sent away to take up residence at seven days a week.
It was fine, except every time she wanted to leave the campus, they had to call her parents to get permission to leave.
She talked to Caroline, almost every day, or at least every day about her day.
Similarly, Caroline talked about her day without Olivia there to hang out with. Caroline had mentioned that she was hanging out with Elena, Bonnie, and Matt. She had mentioned she became a cheerleader with Elena and Bonnie.
On weekends, Caroline and Olivia would call each other and watch Gossip Girl on their laptops together, until lights out at midnight for Olivia, eleven on Sunday.
There were plenty of times that Caroline had mentioned that she felt like the fourth or third wheel around the trio, especially when Matt started dating Elena. Olivia wished she could've been there for Caroline, but she was stuck at Linsly.
Caroline was more of Elena's friend by association. Olivia knew how Elena saw Caroline; annoying, shallow, and mean.
Olivia was the first person that Caroline went to when her dad left Liz for another man and she was there when Caroline was a bit of a wreck over the divorce. Olivia was pretty sure that Elena hated being fourth on knowing that news, despite being somewhat friends with the blonde girl.
So, when Olivia meet Spencer Creed, a glasses wearing boy, Olivia told Caroline all about him. She even had Spencer and Caroline talk to each other over the phone because she wanted her new best friend to meet her other best friend.
Caroline seemed very hesitant at first, but once Olivia assured Caroline that the blonde will always be number one, Caroline seemed to grow to like Spencer. Apparently they regularly texted each other, but not as much as Olivia and Caroline did.
Olivia tried to get her parents to allow Spencer to spend the summer with them, but they refused.
Of course, that was after Olivia realized that what her ancestor, John Gilbert, had written down in a journal was true, her sophmore year – vampires existed.
And that was before Grayson and Miranda Gilbert had died right before Elena's and Olivia's junior year.
