Fourteen-year-old Caitlin Lockhart was born to businessman Jerome Lockhart, and his socialite wife, Belinda Lockhart. They lived in Castelia City, one of the southernmost cities of Unova. They were a wealthy family and had always lived a cushy lifestyle, filled with exquisite food, extravagant fashion, and upscale parties. To her, it seemed that they were always on the move from party to party, always meeting up with people her parents pretended to be friends with, just because they were rich, too.
Caitlin was always confused, though. She was much shyer than her parents. She never liked meeting new people, or going to parties. She would much rather prefer staying in and reading a book, or going for a walk to Castelia Park than going to a yacht party for a day or flying in a private jet to some island, just to leave a couple hours later. How did her extroverted parents raise such an introvert like her? They always tried to make her come out of her shell, but their attempts always failed.
It had been a drab, rainy day in Castelia, when Caitlin's parents decided to sit her down and have a talk with her. "Caitlin, we know you're a shy girl…" her father said, placing a warm, slightly wrinkled hand on her knee.
Caitlin sighed, she knew where this was going, "So, what kind of scheme are you planning to get me to be less introverted this time?" They had done this so many times already, that she already knew exactly what they were going to say.
"I know you're upset now, but when we tell you what we have planned you'll be so excited, honey!" her mother smiled warmly at her. She knew she would be able to become more outgoing if she just gave it a chance.
"Alright, alright, what kind of scheme did you come up with this time?" she asked, pushing a strand of wispy blonde hair out of her eyes. She decided to humor her parents, as they were so enthusiastic about this idea. Maybe it would finally be an idea that she liked.
"Well, we've decided to send you on a trip… to Sinnoh!" her father exclaimed, giving her hand a squeeze, flashing a grin, slightly masked by his bushy moustache.
Caitlin was speechless, she didn't know what to say. She couldn't really decide what to think, "B-By myself!?" The only thing she could really think of was whether or not they would try to cast her off by herself.
"Well, not by yourself. We know you don't like how…" Caitlin's mother was trying to find the right word, "overbearing we can be, so we decided to hire someone to escort you through the region. Someone who knows it well."
"A-An escort!?" Caitlin was shocked. She didn't want to be going around some foreign place with someone she didn't even know.
"Oh, Caitlin, don't be so worried! His name is Darach and he's an apprentice of one of the finest butlers in Sinnoh! And besides, he's only sixteen. You like older boys don't you, Caitlin?" her mother hinted.
Caitlin rolled her eyes. Despite the fact that she was fourteen, they still insisted on finding someone for her to marry when she was older. Although after she thought for a moment, the idea really didn't sound all that bad. A whole trip with another person her age didn't sound that bad, actually. He would probably be better than her crazy parents, and maybe he'd be pretty cool. Caitlin then looked at her mom and nodded, "I'll do it, it sounds like fun. Plus, you've been on me for so long about getting out, I might as well do this to get you off my tail." she smirked.
"Fabulous! Oh, this is just so exciting! Our baby girl, going on her first trip by herself!" her father clapped his hands, grinning from ear to ear. "You leave next week, but we have an appointment arranged for you to meet with Darach in two days. Just so you two can get acquainted and such. Oh, and don't worry, he's taking a boat over here with his master, so he can see some of the sights we have here."
Caitlin nodded, "By the way, how long will this trip be?" she asked. She realized they had never told her just how long she would be gone.
"Oh, about six months or so, give or take a few days," her mother answered.
"S-Six months!? I thought this would just be a couple weeks or so!" Caitlin objected. Caitlin didn't want to be gone for so long!
"Oh, sweetie, please think about how fun it'll be! You'll get to see all around Sinnoh, and meet so many different kinds of people! Please, just do it for us," her mother pleaded, making the saddest face that she could.
Caitlin sighed, she had no choice but to oblige when her parents sounded so sad, or else she would feel so guilty, "Fine, I'll do it. But you have to lend me some money to spend while I'm there." she bargained.
"Of course, baby doll!" Caitlin's father cooed, springing up and spinning around his daughter, causing her to become slightly nauseated.
"D-Dad, I don't think that was necessary!" Caitlin cried as he put her down.
"Sorry, dear, it's just so rare that you let us help you!" her father apologized.
"I understand, you just get excited sometimes," she responded, giggling. Now that she was thinking about it, she couldn't wait to go on her trip and see what Sinnoh had to offer!