Usually, a woman's tears do not bother Damon all that much. Women are fickle, they cry all the time—sometimes even to get what they want. He knows all the tricks. Thus far, only Elena's tears have made him even pause in his actions—although he did what he wanted anyway.
But during the fray, when Caroline made her way out of that trailer and he saw the dried tears and the fresh ones leaking out, something unidentifiable happened in his gut.
He fought harder after that, not that it really mattered, because they were clearly outnumbered from the beginning. And he hates to admit that without that damned warlock, they would have all been dead, but such is life. And he let Stefan take her home—he probably wouldn't have helped her much in that moment—would have said something stupid because he's good at that. And, it's not like he's never treated her badly before either, so really, he should have just stayed away completely, but he doesn't.
He follows her and Stefan to her house and stays hidden outside while they talk and keeps an eye on her when she yells at Tyler and watches over her house while she showers. He's surprised when Stefan has the forethought to bring Bonnie and Elena over, but even Stefan is allowed to surprise him once every century, he supposes.
In the early morning, right before the sun rises, and long after Bonnie and Elena have gone to sleep, he sits on her roof as he waits for the sun to rise. He must have been distracted by something, because all of a sudden, she's sitting next to him.
"Would you have missed this—seeing daylight, that is—if you had never gotten a ring?" she asks softly.
It's the first time he's ever really thought about it, which surprises him. "I've always been a night person," he answers, "but I think I would have missed seeing the sun rise. Brand new day, start over, and all of those colorful phrases."
Caroline smiles and rests her head against his shoulder. Her touch surprises him; after all, she hasn't gotten this close to him since even before she was turned.
"Are you okay?" he asks.
"I will be," she whispers, looking out at the rising sun. "It's a new day, isn't it?"
Damon looks down at her and hides a smile. "Yeah, I suppose it is."