The eternally virginal redhead intrigues him. Not only is she to remain a virgin her whole life, but she seems to have a fang problem as well.
He laughs when she tells him all of this.
She glares and pouts her lip before standing up to walk away.
He grabs her arm and forces her back down on the barstool beside him. "Tell me more," he says.
They have a few more drinks because Damon hasn't had enough to drink yet to tackle this unexpected challenge. Also, he needs something to stop her incessant chatter for a few seconds at a time. He hadn't realized his words were an open invitation to hear her life story.
Later, he takes her back to his hotel room and they experiment
.
Her fangs are out almost the second he pushes her roughly onto the bed (a real boost to his ego), and she allows him to take her virginity three times that night, for—with the help of vampire blood—he found a way to make it not hurt.
The next morning, she kisses him good morning and thanks him as he helps her zip up her white dress.
He never saw her again, but it was certainly an interesting story to tell Caroline later. (At least she didn't have that problem, he told her. She just smacked him over the head.)