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Their first date is an unmitigated disaster.
Elena looks gorgeous in a demure green dress, she laughs at his jokes, and, for a little while, Damon is convinced that this dating thing could actually work out. With the threat of death and Stefan not hanging over their heads, he and Elena actually get along pretty well.
And then the waiter brings their very expensive meals, which Damon ordered so he could show off his fluency in Thai, and Elena takes a big bite after he insists she'll love it.
What Damon Salvatore learns from his first date with Elena Gilbert is that she is deathly allergic to sesame seeds and, when she ingests them, has to be rushed to the emergency room for a shot of epinephrine to stop her airway from closing.
Their second date is marginally better if only because, short of actually killing her, it can't be much worse than the first.
He enlists Caroline's help, which is no easy task considering Caroline Forbes both hates him and feels incredibly loyal to Stefan, but after enough pleading and blatantly using her feelings for Elena against her, Caroline suggests a picnic. Damon doesn't think he has been on a picnic since he was human, but he puts together a decent meal (calling Elena three separate times to make sure she doesn't have any other food allergies she hasn't mentioned before) and even buys an honest-to-goodness picnic basket.
The smile on Elena's face when he leads her to the spread is positively beatific.
They sip champagne, eat strawberries, gorge themselves on crunchy French bread and brie, and Damon almost thinks he has made up for nearly killing her via Thai food when he hears Carol Lockwood calling both of their names.
As it turns out, the Mystic Falls Ladies' League holds their bimonthly meetings in the gardens of Wickery Park. By the time Carol Lockwood finally leaves them be, the champagne is warm, the fruit is beginning to attract ants, and Elena has agreed to attend the next meeting of the league.
What Damon Salvatore learns from his second date with Elena Gilbert is that she is incapable of being rude to anyone, especially if that person references Miranda Gilbert's civic involvement and her pride in her daughter.
Elena plans their third date.
He arrives at the Gilbert household to find Elena in sweats, a recently delivered pizza on the kitchen table, and a handful of DVDs awaiting selection. His confusion must show on his face because Elena declares, “If we don't plan anything, it can't be sabotaged, right?”
It isn't what he would consider an awesome date, but, after an emergency room visit and the Mystic Falls Ladies' League, he isn't going to complain. Instead he gamely allows Elena to choose some stupid romantic comedy, toes off his shoes, and digs into the pizza. As the characters on-screen are debating losing their virginities, Elena turns to him and asks, “Was Katherine your first?”
“What? No!”
Elena laughs. “Why do you sound so offended? It's an honest question!”
“Because I was 25 when I met Katherine. You really think I waited that long to have sex?”
“I don't know. It was 1864. I just assumed manwhoring wasn't acceptable then.”
He huffs with perceived slight. “No, I was not a virgin when I slept with Katherine.”
“Then how old were you? Who was it?”
If he could blush, he would; this is not a story he wants to tell. “Why does it matter?”
“Um, because you said the whole point of dating was to learn about each other. I'm just trying to learn.” She smiles mischievously. “It wasn't your cousin or something, was it?”
Playfully glaring at her, he sighs, “No, it was not my cousin. It was...Her name was Emma Lockwood. We were...We thought we were going to get married, so it wasn't a big deal.”
“But you didn't marry her.”
“No.” He rubs at his face; it has been so long since he thought of Emma, and, despite what people said, the pain had not lessened. “She married someone else. My father didn't think I was an acceptable husband for her.”
Elena blinks in shock. “Wait. Your father - “
“It was a long time ago,” Damon cuts in, hoping this will be the last time they ever talk about this. Trying to change the subject, he continues, “I assume Matt was yours.”
She nods, content to let the subject drop for now. “We were fourteen.”
“Slut,” he teases, laughing as Elena kicks at him halfheartedly.
Later, when he is getting ready to leave, Elena stands on her toes, brushing her lips against his cheek, and he stills at her words. “For what it's worth, what your father said...It isn't true. You're good enough.”
What Damon Salvatore learns on his third date with Elena Gilbert is that she is incapable of withstanding someone else's pain, even pain which is 150 years old.
Their fourth date is the single most awkward event of Damon's life.
They're at Elena's house again, Damon having insisted they watch Casablanca since Elena had not seen it before; he knows Elena is bored, and it isn't exactly the worst thing in the world when she starts kissing his neck. In fact, it's kind of amazing, especially when she draws blunt teeth over his pulse point, a move which makes him harden instantly. Before he's even aware of it, they are making out like two teenagers on the living room couch, and it's incredible how normal he feels.
“Damon,” she pants, a little needy, and Damon inhales sharply through his nose when she tugs his shirt up, urging him to take it off. Elena's hand are warm and gentle against his chest as she explores, and, when his own hands go to the bottom of her top, Elena surprises him by sitting up and tossing it away, leaving her in a sheer black lace bra.
“Fuck,” he whispers. Elena laughs, pulling him back down for another kiss; her skin is so hot, the blood pounding in her veins, and Damon feels it, the urge to sink his teeth into her, to feed in every way he can. As he kisses his way down to her breasts, tonguing her nipple through the rough lace of her bra, Elena twists her hips as a soft moan escapes her lips; he shifts his body, his hips settling into the cradle of her thighs, and Damon moans as they begin to churn against each other.
“You feel so good,” Elena purrs, wrapping her legs around him, canting her hips in an attempt to gain more friction.
Kissing Elena is so different from anything he has imagined; he had always expected Elena to be demure, maybe even shy, but there is nothing hesitant about her now. It is powerfully arousing to see how free she is like this, unburdened with worry or guilt, and Damon wonders if he even deserves this, deserves her.
So wrapped up in the feel of Elena against him, the press of her mouth and warmth of her body, Damon is blindsided by his orgasm. As he quakes against her, pleasure singing through his veins, humiliation hits him nearly as quickly. The moment he feels his breathing regulate, he pushes away from Elena, startling her; the wetness in his jeans makes him even more angry, and he thinks of the human boy he used to be, the one so far away from who he is now.
“Damon, wait,” Elena pants, reaching for his wrist and missing as he steps backward.
He leaves her on the couch, half-dressed and looking so goddamn beautiful he can barely stand to look at her, mumbling an apology even as he rushes from the house.
What Damon Salvatore learns on his fourth date with Elena Gilbert is that he is so far out of his depth, he may just drown.
Their fifth date isn't a date at all.
He is reading a book in his room, reclined on his bed, when Elena enters the room, her face set with determination. She's wearing a sundress, her hair falling in waves around her face, and Damon idly remembers she had to go to some luncheon for her mother's charity.
“Did we have plans - “
“Shut up,” Elena orders, startling him. Damon isn't sure what she's angry about, but, as she climbs onto the bed, throwing one leg over his body, Damon realizes she isn't angry; she's aroused.
It happens so fast, he doesn't have time to think. One minute Elena is straddling him, ranting about how they've been trying too hard and she's sick and tired of him trying to dictate the pace of their relationship, and the next she is wrenching open his jeans and sliding down his cock. It isn't until he is completely inside of her that he realizes she wasn't wearing panties beneath her dress, and it only serves to make his blood hotter.
They never manage to get their clothes off, not until Elena has shuddered through two orgasms and he has shouted her name like some teenage boy; when Elena finally sheds her dress and Damon gets to see her completely bare for the first time, he blurts out, “Oh, I love you.”
Elena quirks an eyebrow, a hint of a smile on her face before letting her eyes drift shut. “I know. I love you too.”
What Damon Salvatore learns on his fifth date with Elena Gilbert is that it pays to let her surprise you.
Their sixth date is the Founders' kick-off party.
He doesn't particularly want to go, but Elena talks him into it, reasoning that he is one of the last of the Salvatores the way she is one of the last of the Gilberts. And though he makes a lot of noise about how boring this is and how he doesn't understand why she cares, he still puts on a suit and appreciatively eyes Elena in her red dress.
Damon doesn't recognize the woman Elena is talking to, but, as he sidles up beside her with two flutes of champagne, Elena slips an arm around his waist and says, “Damon, this is Clara Fell. She worked with my father at the hospital. Mrs. Fell, this is my boyfriend, Damon Salvatore.”
She's never called him her boyfriend before; when he points this out to her, Elena laughs.
“Just because you don't hear me say it, doesn't mean I don't.” She stretches up on her toes, kisses the fullness of his bottom lip. “You can call me your girlfriend if you want.”
What Damon Salvatores learns on his sixth date with Elena Gilbert is that, of all the things he has ever been called, being referred to as Elena's boyfriend is the title he is most proud to wear.