Closed starter @malka-lisitsa
Home from the war on a furlough, Damon had absolutely no responsibilities and nothing to do. He'd never been father's favorite, but if he had stayed no doubt he would have been given the work that now went to his younger brother. He was certain that father was relieved that he didn't have to do so out of duty - believing his elder son to be feckless and irresponsible.
In truth, Damon might have stepped up if given the opportunity and the trust, but never receiving either? He was content to let Stefan be the golden child. It left him with so much more free time.
A distinct advantage when it came to wooing their unexpected houseguest. The beautiful and beguiling Katherine Pierce. Of course Stefan expected priority when it came to the young lady, he was the one to receive her after all, but all was fair in love and war. Miss Katherine was far too much for his younger brother and Damon was shamelessly using that to his advantage - believing himself to be the better choice.
This was where he found himself, on a lovely Thursday afternoon, happening upon the young lady in their expansive gardens. Aiming for surprise, Damon snuck up to her and tapped her on the shoulder.
"Has my dear brother left you alone again?"