Damon hates his father.
Damon belongs to one of the founding families of the town that he lives in, Mystic Falls, Virginia. Because of this, his father, Giuseppe Salvatore, believes that Damon should marry a member of another founding family just like he did. Since his birth, it has been arranged for Damon to marry Caroline Forbes, but he has little interest in her. Sure she's beautiful with golden blonde hair and bright blue eyes, but he shares no chemistry with her in the slightest. All of his life, he has dreamed about marrying someone with a passion for life, someone who he could argue all day with, but he could never stay mad at, someone who he completely and utterly in love with. But no, he was stuck with Caroline Forbes for the rest of his life, the girl who acts prim and proper all day, the girl who feels the need to control everything in her life and other's, the girl he doesn't love even the littlest bit. His arranged marriage to Caroline was just one of the many reasons that Damon Salvatore hated his father. He abused him and his younger brother, Stefan, their entire lives, he sent his mother away when she was dying of consumption, and now he took away the choice of who he gets to spend the rest of his life with. And for that, Damon will never forgive his father.
It's his wedding day, yet Damon has never felt more miserable in his life.
They're having a huge and lavish wedding, nothing less would have been acceptable for Caroline Forbes. The scenery is perfect: it's a nice sunny day, there are arrangements of red roses everywhere, and everyone is wearing their Sunday best. The entire town of Mystic Falls is in attendance since it's a marriage between two founding family members. Today should have been one of the happiest days of his life, but Damon feels like he is signing his own death certificate.
He is now standing at the end of the aisle with his brother and the pastor by his side. Just like Damon, Stefan looks depressed, he always had a thing for Caroline. The pianist and small orchestra starts playing and everyone stands up from their seats. As Caroline starts to walk down the aisle with her father on her arm, the rest of his life starts to flash behind Damon's eyes. At first it would seem like they had the perfect marriage: they would have two beautiful children, a boy and a girl, and they would both have blue eyes like their parents, they would run the family plantation together and would be immensely wealthy, and they would travel the world and tell everyone about their adventures. But behind closed doors, they would grow to hate each other: Caroline would just sit around with the other married women and sew and gossip all day, he would drown his sorrows in bourbon, and they would have boring sex a few times a year because they felt obligated to since they were married. And his vision flashed forward to when he was on his deathbed and all he could think about was how much he regretted marrying Caroline Forbes.
By now, Caroline is reaching him and Damon ignores his daydream. Backing out of the wedding would be a huge dishonor to both his and Caroline's families. The pastor starts the ceremony and Damon drowns him out, it turns out that he can't shake his vision of his future. The pastor now says something to him and he takes that as his cue to start mumbling his vows. Caroline then repeats hers and they are now pronounced as Mr. and Mrs. Damon Salvatore. The pastor now tells him that he can now kiss his bride, and Damon hesitates before giving Caroline a quick peck on her lips. There wasn't even a little spark between them.
They now go through their reception, and the entire town congratulates them on their marriage, including his father. Damon just brushes him off, like he actually cares about him. He shares a bland piece of cake with Caroline, and they go through every wedding tradition. Everyone looks like they are having a great time, everyone except him.
Suddenly it's their wedding night, and they are now expected to consummate their marriage. Damon was already not a virgin, but Caroline definitely was based off of how nervous she looked. They pulled off their clothes and he sighed as he started thrusting in and out of her. Yep, there was definitely no connection there. When he was about to finish, Damon pulled out of her, he definitely did not want a kid with her right now. After that, he fell asleep next to her with nothing but regret filling his every thought.
Damon wakes up still regretting the previous day.
Men joke with him about his wedding night, but he just brushes them off, he's not in the mood. He sits next to his father and brother at the table, and eats his breakfast in silence. They try to make conversation with him, but Damon ignores them, they aren't the ones who now have to spend the rest of their lives with someone they dislike.
He goes through the rest of his day trying to avoid Caroline: he goes riding with Stefan, he helps run the plantation, and then he goes into town with the excuse of visiting his best friend Alaric, but in reality, he goes to the town's pub to drink away his regret. He's sitting in the corner of the pub nursing an entire bottle bourbon by himself when a man rushes in and shouts about how we were now at war with the Yankees. Men start scrambling out of their seats and rush over to the town hall to enlist themselves. Damon ignores them and keeps drowning his sorrows until a thought comes into his head: if he enlisted himself into the war, he could ignore his problems with Caroline for awhile. And Suddenly, Damon is a confederate soldier being shipped off to a war he doesn't care about.