At the time, Damian didn't know what it meant to fall for a person. Feelings were meant to be pushed deep down inside a being's heart or crushed altogether. At least that's what the League of Assassin had taught him from birth.
So when he first began to understand love, it was right around the time he had first joined the Teen Titans. There, he met you, one of the few heroes that welcomed him to the team. Your arms were wide open for him, even as he insulted and pushed you to hide away an ounce of care he has for any of his teammates. Eventually, thanks to your stubbornness, you crumbled down his walls and the two of you began to date.
It was also around the time, when he finally let his feelings be shown, that he began to feel something for another teammate. Towards Raven.
He knew that it was a low blow for him to break up with you and then develop a relationship with Raven right away. It wasn't even a few weeks before he had become protective of Raven, both with endearing words and pushing himself in front of battle for her.
Guilt for any of his actions, small or big, was not also taught by his mother and the league. But it began to eat him inside as he watched you slowly break every day ever since you two broke up. And apologies were not exactly something he could see himself doing. Not now or... ever.
Eventually, he and Raven began to have some problems themselves. With Raven being an empath and Damian being closed off, such a pairing was not at all as compatible as he imagined. Now, he was regretting ever breaking up with you.
"I'm sorry." He said after so much intense build-up to say those two words. His eyes weren't even looking at yours as he stood in front of your bedroom door. His arms were crossed over his chest and his head was ducked down. "For everything. For leaving you. For Raven. Everything."