Mystic Falls, VA September 2, 1864
"Jessa, I'm not sure setting up your own household at 14 years old is the best avenue." Mr. Salvatore was saying. "You're still very young, and I think your parents wouldn't want me to allow it. Not just yet."
She had rushed downstairs before the rest of the house had woken and burnt the bedding and her night shift. The kitchen tended to keep a fire burning and luckily the fire was roaring before she came down. Then she waited to ambush her guardian as he woke and rushed to his office. Her hope was to argue her case and get the allowance to move forward. Unfortunately, that wasn't the case.
"I can see you're angry with me." He said, forcing her to look up. "Jessa, we don't live in a world where a very young woman is allowed to live alone. If you give me two years, your engagement will be official and then the wedding can be rushed if necessary."
She showed her shock at the news of an engagement. "Engaged?" She asked, curious as to whom her guardian had picked for her.
"Yes, Jessa." Mr. Salvatore said, sitting harshly down in his chair. He watched as she fell into her own. "You must have known that's what your future held?"
She flashed back on her mother readying and the corset of doom. She nodded, feeling lost. "Of course, I just hadn't realized…when."
"I've been talking to Stefan. As soon as you turn 16, we can announce it. Then if you wish, the wedding can take place a month later. At that time, you two can move into the home your parents' had built."
She gasped. "Stefan?!" Looking at her guardian with fear and the feeling of nausea.
"Well, of course. Surely you must have had an idea that he's the one your parents' settled on?" Mr. Salvatore said, taking her cold hands. "Your parents were Lily and my best friends, Jessa. Your birth marked a moment when we realized our families could join. Together, Mystic Falls will be the town built by your families. The two of you, even without the title of Mayor, will be the first family."
He said this as though it were a coup. Which to him, it was. Stefan, a boy she barely knew, for all their living in the same house. The brother of her very best friend. Someone she'd never let in. She shook her head. She wanted none of this. Not a moment.
"Stefan doesn't want this." She said, sure of that.
"It truly doesn't matter what Stefan wants." He said, tossing that concern aside. "Nor, unfortunately does your want matter in this. Your parents asked, Jessa. Don't make me go against their wishes."
She withdrew her hands from his. She felt sick, knowing that Stefan knew and knowing that this was one more thing to put a target upon her back with Katherine. Blinking back tears, she stood.
"Mr. Salvatore, I'm not feeling well. Please tell Hattie to bring me some tea." She said, barely above a whisper. Then she fled, not far, for she truly was a bird in a gilded cage. To her room, where she closed the door quietly, and cried. Unsure of what was worse, marrying someone she barely knew or knowing that a murderer lived in the same house and would try even harder to kill or ruin her.
Mystic Falls, VA September 10, 1864
"Thank you so much, Jessa, for offering your help." Mrs. Lockwood said, watching as the young girl flitted around the house, making notes. "You always have such an eye for these things. I mean, Damon's last birthday party was so lovely."
Jessa smiled and nodded, making note of where the tables should be placed. She felt numb and had for days. Seeing Katherine when she finally came down for dinner, and watching her acknowledge that death wouldn't come easy for Jessa was terrifying. The would-be assassin hadn't made another attempt, but her servant, Emily had begun watching her every move.
"Have you found a dress?" Mrs. Lockwood asked, as she too made a note about floral arrangements.
A dull sadness passed over her as she recalled the day she found it, "Yes, I did. It's quite lovely, I just do not look forward to the corset."
Mrs. Lockwood giggled agreement. "Beauty is pain, I believe someone wrote."
"I wish they chose not to." Jessa said, with her own smile.
They stopped for tea, and while sitting Mrs. Lockwood gossiped.
"And then, Mrs. Fell said her son Christopher was obviously a better match, and I truly thought Mr. Gilbert's heart was going to stop." She said, laughing. "I have heard that you have a guest at the Salvatore house."
Jessa's stomach dropped. "Yes, an orphan of the Atlanta fires. Katherine Pierce."
"Is she as beautiful as the rumor has it? I know Michael and Matthew were waxing poetic…"
"Her looks are agreeable, I suppose. Stefan seems to appreciate them." Jessa said, smiling sadly.
"I've heard another rumor." Mrs. Lockwood said, eyes twinkling. "About Stefan and you."
Jessa sighed. "So have I." Her smile dropped and Mrs. Lockwood looked confused.
"Are you unhappy, Jessa?" Mrs. Lockwood asked, her maternal instincts surfacing.
"Of course not," she answered, shaking her head. "The Salvatores have become my family, I suppose it only makes sense that it becomes permanent."
"Is it the choice of brother?" Mrs. Lockwood asked, digging for information for the next gossip session no doubt. "I know you and Damon were normally joined at the hip."
"No, Damon and I are best friends." Jessa said, correcting her. "He taught me about things that the storybooks that my papa taught me to read with didn't. And he gave me my nickname."
"I understand, but Jessa, friendship can become more with the right cultivation." Mrs. Lockwood said, gossip aside, she couldn't stand to see the girl before her sad about her fate.
"I'm sure you are correct, Mrs. Lockwood, I am fairly certain my issue is simply with the notion of marriage alone. I'm only 14 after all." She said, sadly.
The rest of the day went the way it should. She finished her notes, and gave them to Mrs. Lockwood with the assurances that she'd continue until the day of the party. Leaving with Hattie to attend her, they walked carefully home. Even as Jessa knew that they were being watched.
Mystic Falls, VA May 10, 1861 (I KNOW THIS CHANGES THE TIMELINE)
Jessa watched as Lily Salvatore wasted away. Her adopted mother, the woman who gave her more in barely a year than her own mother did in ten was dying. Tuberculosis. Even a ten year old knows that. She wiped Lily's brow with the cool water Hattie brought her.
"Jessa, you shouldn't be here." Lily's hushed voice said. "You could get ill."
Jessa scoffed, she'd never had so much as a cold. "Lily, please. I'm fine. Don't send me away, please."
Lily reached out and took her adopted daughter's hand. "Jessa, I always wanted a little girl. I never wanted your parents to die, but looking after you, even for so short a time was a gift. You are a gift. Never forget that. I love you, please tell the boys as well." A coughing fit took over and Jessa noticed that there was more blood on the rag than ever before.
"Jessa," a deeper voice, belonging to Mr. Salvatore broke through her careful watch of Lily. "You must leave, please. Lily needs to go to the sanitorium."
Tears rushed to Jessa's eyes. "Please," she begged, not wanting to lose another mother. "Let me be with her."
He pulled her carefully from the room. "Jessa, dear, you know you cannot stay with her. She's dying, even Lily knows that."
"I can't lose her, too." She cried. Sniffling. She didn't hear Damon come up behind her. He pulled her to his chest.
"Mother wouldn't want you to go, Jessa." He whispered into her hair. "She'd want you to stay here with us." And lower, so only she could hear, "with me."
Mystic Falls, VA September 18, 1864
She listened to Stefan entertain Katherine Pierce in the garden beneath her bedroom window. They were playing and laughing and honestly she couldn't summon of the urge to care. Instead she was locked in the replay of her losses. Her parents and Lily dying hurt her so much, but knowing that she herself couldn't die made her curious. What if her parents weren't dead? What if they survived the fire?
Unfortunately that thought upset her more than their deaths had. If they were alive, why weren't they with her? Why did they leave her? Here, among happiness and hell?
Suddenly a familiar and very missed voice broke through her thoughts. She could hear Damon in the garden. Gasping she rushed to the window and looking down, her happiness turned to heartbreak in seconds.
Damon, her best friend, someone she was terrified of losing stood below her window where she could observe without being seen. And in a second her heart broke as she watched Katherine Pierce take a place she never wanted to occupy. Seeing them laugh and play, watching Stefan join, Jessa clearly saw her life, position, and self-replaced in both faces. She was certain neither even recalled her at all.
Katherine, without murder, won. And Jessa, knowing this as clearly as her knowledge of anything, began planning her escape from Mystic Falls.