He initiated the first kiss—although on a scale of kisses, it hardly qualifies. It was a simple, "It's nice to meet you, Caroline," after Elena stuttered an introduction. He then grabbed her wrist and kissed her hand as the words fell from his lips.
He hid a grin as he watched her restrain herself from curtsying in response to the old-fashioned mannerism.
Sense seemed to return to her then, for she said, "The pleasure is all yours," and walked away.
Nodding in the blonde's direction, he said to Elena, "Interesting character. I plan to get to know her."
Elena's wide eyes amused him.
-x-
The second kiss was an accident—or, at least, he's going to maintain that it was until he breathes his last breath. Caroline, on the other hand, insists that he's a dirty, rotten, scumball—her words, not his—and that he had no right to do that to her.
But it's not his fault. Really, how was he supposed to resist the allure of the blonde little thing in that all too revealing cheerleader outfit of hers with crimson blood on her lips…he's getting ahead of himself.
They were at the Salvatore boarding house. It was early afternoon. Bonnie had called everyone over because she found a spell in the grimoire that would allow her to duplicate the effect of the dagger used to kill him (he did still hold a bit of a grudge for that) onto a more ordinary kitchen knife. Caroline, as she explained when he casually remarked about her state of dress, had cheerleading practice in ten minuets and she only came by to get herself a snack. "Bonnie's filling me in tonight at the slumber party," she had said.
Elijah followed her down to the freezer where the Salvatores keep their very humane stash of bagged blood. He stayed out of sight and just watched the object of his curiosity.
But sometime after she ripped open the bag and started sucking, he stepped into her line of sight, scaring her, and she stumbled.
Blood got everywhere, including all over her mouth, and as mentioned above, he could not resist the allure of those blood red lips with blood actually on them, so he propelled himself in front of her and kissed her, savoring the taste of blood on her lips.
Needless to say, the episode resulted in a slap to the face for him and some yelling on her part.
-x-
The third kiss was deliberate and all on her.
He was minding his own business, talking up a very nice young lady that he planned on feeding from that night—he's not the Salvatore's, after all, and prefers live blood—and in walked sweet, delectable, little Caroline. She was glaring at him because she was smart enough to deduce his purpose and she obviously didn't approve.
She walked right up to him and demanded he speak to her alone for a moment.
He obliged, politely excusing himself and asking the young woman to watch his drink.
"Is there something you desire?" he asked when she got him alone in the hallway next to the bathrooms. It's not particularly the venue he would have chosen for his first meeting with a willing Caroline, but when life gives you lemons and all that nonsense.
"What the hell do you think you're going to do with that woman?" she asked, getting straight to the point.
He shrugged. "I'm hungry, she's nice; it seems like a good plan to me."
She just glared. "Dead people popping up in Mystic Falls are always a red flag to the Council. They seem to be getting smarter lately and we really don't need that now."
Elijah rolled his eyes. "I'm not going to kill her, Caroline," he said, playing with her name as it rolled off his tongue. He really liked the sound of it. "What kind of monster do you take me for?"
"You don't want me to answer that," she retorted.
He sighed. "If that is all, I've got a date to get back to," he started, waking back to the bar, but he didn't get a chance to finish, because all of a sudden, her lips were on his and he was enjoying every second of her impulsive decision that he knew she was going to regret the moment she pulled away. He didn't care, though, for he was getting exactly what he wanted.
He was right, of course, and she slapped him for taking advantage of her when she felt the very real evidence of his enjoyment. She stormed out after that, and he didn't see her for a week.
-x-
The forth kiss was, again, all on her, but this time, he'll allow her the excuse of being completely, totally, without a doubt, drunk off her ass.
As he later learned, Caroline had seen her human boyfriend of sorts with another woman. He wasn't cheating on her, for they were not together, but technicalities and all, and it still hurt, so she stole three rather large bottles of vodka from the Salvatore boarding house and made herself at home in the woods near her house.
That was where he found her, drunk even by vampire standards.
He had offered to take her home and get her settled, but she had refused until he pointed out that her mother could hear her screaming and then she'd have whole different kind of problem to deal with.
She was rather meek after that, and he walked with her for a while before he realized that it would take them a long time to get back to her house for she was in the stumbling phase already. So, being the considerate gentleman that he was, he picked her up and quickly deposited her onto her bed.
She hadn't allowed him to leave, even though he'd offered, so he sat next to her and listened to her talk about her problems. Most of them were quite petty, and he had to remind himself that even though she was a vampire, she was also only seventeen years old. Then, she got to talking about him, and he wondered if she even knew who he was for a moment, because her blunt honesty was a little bit frightening.
"If I didn't know you want or wanted to kill Elena, I might actually like you, you know," she said at one point.
"I think you like me anyway," he replied, saying what he wanted to say rather than what he should say.
Caroline has surprised him when she shrugged, leaned forward, and brushed her soft lips against his for the briefest of seconds. "Maybe," she whispered before lying back down and closing her eyes. "Too bad we'll never find out."
"We already have," he whispered before leaving that night.
-x-
The fifth kiss was mutual, but he had to wait several years for that one.
It was after Klaus had been taken care of, after Stefan rekindled his love for Katherine, after Damon finally got the girl, and after Caroline's self-discovery expedition throughout Europe.
She came to him at his home in England and walked right into his bedroom where he had been sleeping.
"So," she said, "I was wondering if you want to find out what this could be."
He didn't have to guess what she was talking about; he just leaned in and…well, a gentleman never reveals those kinds of secrets about a lady.
