This idea has been haunting me ever since I watched 2x08. Hope you like it!

You Don't Deserve Her

"You don't deserve her, Damon."

Now where had he heard that before?

FLASHBACK

Rather nervously Damon stepped into his father's study and politely knocked on the door to attract Giuseppe's attention. His father looked up from his writing, shot him a glance and then turned back to his journal.

"What is it, Damon?" he asked casually.

"There is something I want to talk to you about, father," Damon declared.

"I'm listening. But make it quick. I am very busy as you can see."

"I wish to marry Miss Katherine," Damon blurted out without missing a beat.

"What?"

Giuseppe's head snapped up. He fixed his son. His gaze was horrified and menacing at the same time.

"I wish to marry Miss Katherine Pierce," Damon repeated louder and firmer now.

What happened next was completely unexpected by Damon. Giuseppe burst out laughing.

"I'm serious!" Damon snapped.

"Oh, I know. Believe me, I know," Mr. Salvatore said. "I am laughing because you actually mean it."

"Of course I do!"

"You are being ridiculous! Giuseppe shook his head. "You don't deserve her, Damon! A woman as beautiful and kind as Miss Pierce."

"But–!"

"You are being ridiculous!"

"You come here, daring to meet my eye after turning your back on your comrades at the confederacy and now you think you can just marry the most beautiful and wealthiest woman of this town."

"I love her!" Damon emphasized.

"You are a fool!" Mr. Salvatore shot back. "How can you even assume that Miss Pierce would accept the proposal of a lousy man like you?"

"Because she loves me, too!"

"In your dreams she may," his father replied, shaking his head. "Besides, Miss Pierce is already about to be engaged to another man."

"What? No, she said there was no other man in her life," Damon said, trying to sound convincing but even to himself it wasn't.

"I told you, you are a fool," Giuseppe repeated.

"I don't believe you, father. Just tell me where I can find mother's ring. I don't need your blessing."

"I will not," Mr. Salvatore clarified. "It is safely locked away at a secret place and you will never learn about it until the day I die!"

Damon shook with anger but he pursed his lips, biting them rather. His eyes travelled down to Giuseppe's hand – with which he had been gesticulating wildly – and froze.

"Say, father, where is your ring?" He knew that ever since his wife had died his father had never ever taken off the ring.

"I gave it to your brother," Giuseppe answered calmly.

"Why?" Damon inquired suspiciously.

"Because," Mr. Salvatore replied slowly. "he wishes to marry Miss Pierce, too."

"What?" Damon burst out. "No! He can't! He mustn't!"

"Yes, he may," his father corrected. "Your brother is an honorable man who happens to be to Miss Pierce's liking. He deserves this woman more than you do."

"Please, father, give me another chance. I can be a better man. I can prove it to you! I really do love Katherine. I know I can make her happy! Please, father, give mother's ring to me!"

"No, it is too later for that. I have made up my mind. Now get out of this room, please."

Damon shot him a deathly glare. "I despise you, father! Be damned!" he shouted and turned around to leave.

"Damon Giuseppe Salvatore, don't swear!" Mr. Salvatore scolded him but Damon had already exited the room.

Later that day during the ball the engagement between Mr. Stefan Salvatore and Miss Katherine Pierce was made public. After the announcement Damon felt sick and wordlessly left the party. He confronted Katherine about the engagement and begged her to undo it but she simply told him that he should have proposed to her sooner.

And from that day on Damon had been alone.

END OF FLASHBACK

Reliving the past Damon came to the conclusion that he would never deserve to be happy with a woman as gorgeous as Katherine or Elena, even if he would be the first one to propose to them. He would always lose the competition that had never been a competition in the first place. Elena wasn't his and she would never be, he thought sadly and put the lapis lazuli ring back into the box.