When he makes good on the promise made to himself. The one Damon looked upon so skeptically. A life of his own, away from this town, from Elena. To finally find some place, somewhere, he can belong without falling back on old habits.
He gives no goodbyes, driving off in his little red Porsche, without looking back. Unlike previous attempts to escape the nostalgia of Mystic Falls, he doesn't immediately head for Chicago rather, takes the highway due south with no particular destination in mind.
It's freeing, the complete lack of a plan, and idea to see the world without guilt or shame weighing him down. Caroline shifts in her seat, another impulsive irregularity, his invitation and her acceptance all at the last minute.
Her hair shines in the moonlight, looking stark white instead of the usual yellow tint, as her head rests against the window watching the night streak by. He wonders what she's thinking, almost utters 'tell me things', but doesn't.
Instead he drives, trying to keep the smile from his lips, and his eyes on the road.
Two in the morning at an all night diner, in a town with the curious name of Missing Mile, North Carolina. The place is empty save for a single waitress, the cook, and the two of them. No cars have passed on the highway the half hour or so they've been seated, leaving Stefan to wonder about the practicality of a twenty-four hour eatery in such a low traffic locale.
He looks down into the half empty cup of coffee, the reflection of his left eye, holding his attention. Caroline works her way through a second piece of pie, silverware jabbing eagerly into the cinnamon sugary confection, a delighted moan stirring in her throat.
"Enjoying that?" Stefan asks with a pointed gaze.
"It's good," she replies, jabbing the fork in his direction. "So good it should be illegal."
Nodding his acceptance, he takes another sip, and contemplating where to go from here. Might be nice to head down to Key West, or just circle the gulf. Maybe he'll leave it up to chance and a last second decision on a junction somewhere in Florida, or Caroline will voice her own opinion along the way.
Either way, it's not a heavy decision, this new found freedom practically its own reward.
Nearly dawn in Biloxi. They stumble into an elevator smelling of one too many martini's and cheap cigars. Caroline can't stop giggling, even though the last funny thing he said was nearly ten minutes ago, she's still thinking of the guy who tried to pick her up in the bar and she compelled into doing the chicken dance. Or maybe it's just the sheer amount of alcohol consumed. Honestly, he can't remember the last time he drank is such excess.
Hands on Caroline's wrists to hold her steady, the doors open, and it takes nearly five minutes to find their room. Her giggling comes to a halt the moment they realize there's only one bed. Sharing an awkward look, Caroline kicks off her shoes before collapsing on the left side of the bed.
Stefan stands there, unsure how to proceed, when Caroline pats the mattress with a few soft slaps.
"You're not sleeping on the floor," she says, practically pulling the words from his mouth. "Just no getting handsy."
Shedding his own shoes, he falls onto the right side, laying rigid until her slow steady breathing lulls him to sweet oblivion.
There's hair in his mouth, when the sun rises, and a head on his chest. He tries hard not to wake her but one little shift and her head pops up, looking at him bleary eyed, it doesn't feel as awkward as he thinks.
Austin, Cherry Creek Park, watching Caroline spread the red gingham blanket on the grass before pulling sandwiches from a wicker picnic basket. At first Stefan looks on confused, having no idea where she acquired either of these things, but sits down obediently at her request.
She puts a sandwich in one of his hands, a cherry cola in the other, and sighs contentedly after the first bite and drink of her own.
"I get the feeling you planned this way before now."
"I love picnics," she replies with a shrug. "Is that really so surprising?"
Cracking open the soda, he shakes his head no, unwrapping the sandwich and taking a bite. Spam. Now that is surprising.
"My grandma used to take me all the time," Caroline goes on. "When my parents were splitting up."
"How old were you?"
"Thirteen. I mean, at the time, I kind of hated it you know? They just seemed so old-fashioned and lame. But, I was kind of stuck because I had to stay with her due to the state not giving my dad custody, and mom was never home enough to-"
She stops, purposely taking a drink of her soda.
"I don't know why I'm telling you this."
"You can tell me anything," Stefan says.
"Yeah," she agrees. "I know."
With the sun radiating an unbearable heat in the small town of Bisbee, Arizona. Caroline ducks into a shop, pulling on the crook of his arm, as the sweet sensation of air conditioning overtakes them. She gasps at sight of the inventory, all vintage glamour gowns of a time long past, and immediately heads for flashy looking number colored in deep burgundy.
Though his enthusiasm doesn't match hers, he can appreciate the fact that it looks like something that could have been worn to the Oscars back in the fifties. A little old lady shuffles to the counter, pushing eighty by best guess, and both assume her to be the proprietor. She smiles brightly at the way Caroline carries on, offering a wink at his platitude, and asks if there's anything in particular they're looking for.
"Actually, we just came in to get out of the heat," Caroline admits. "I'm sorry, that's terrible."
"Happens more than you think," she offers. "Would you like to try something on?"
"Oh no, I couldn't."
"This is the part where I insist," she presses, rounding the counter and snagging a gown of off white silk from one of the racks. "My name is Lynn, and trust me when I say, every girl needs a bit of glamour."
Caroline catches Stefan's eye, and he merely shrugs, as the blonde squeals in delight heading for the lone dressing room.
A few minutes later she emerges, looking elegant, regal, and a slew of other adjectives he can't quite think of on the spot.
"Oh my dear," Lynn says clapping her hands together. "You look just like Veronica Lake."
Better, Stefan thinks. She looks better than Veronica Lake.
Big Sur at barely six-thirty in the morning, when Stefan shuffles sleepily through the screen door, to take a seat next to Caroline on the deck of their rented shack on the beach. There's a cup of coffee in her hand, which she blows into but doesn't drink, giving him a welcome smile.
"Are you always going to be up at the crack of dawn?" He jokes with a playful nudge to her shoulder.
"Habit," she replies with a shrug. "So many things to do, so little time to do them."
"Planning committee. Yearbook. Glee club. Student council. Cheerleading."
He chuckles softly.
"You don't have to do any of those things anymore."
"I know," comes her reply. "But it's like, six AM, and my eyes pop open."
Stefan nods, unsure what to say to that.
"I like it here," she admits a few minutes later, finally indulging in her coffee.
"The ocean," she corrects. "The air. Not so many trees to make you feel claustrophobic."
"Sounds like you're glad to have left."
A sigh is all she gives.
"It's not like I hated it there," she continues after a moment. "It's still home, you know? I just never planned on staying. The day after graduation, bam, I was so gone."
Stefan looks at her. "That was your before plan, wasn't it?"
"Before I became a creature of the night? Yeah, I wasn't even going to say goodbye."
"I find that hard to believe."
"I don't know if I actually would have done it that way, but it was the plan. Finally do something no one expected of me."
Stefan gives a teasing pinch at her elbow.
"I think you accomplished that."
She smiles into her mug.
"Guess I did."
On the Oregon coast in a town so encompassed in fog they couldn't see any signs for a name. Caroline wanted to find the house from the Goonies, but neither she nor Stefan's phone gets a strong enough signal for internet, and can't for the life of them remember exactly where it resides.
They walk into a drug store, one of those old fashioned ones with a lunch counter, and buy two ridiculously bright colored rain slickers to battle all the moisture outside. Crossing the highway, they find a trail leading to the beach below, covered in more rocks than sand.
Though they've been on the road for weeks, going here and there, this oddly feels like the most adventurous thing they've done so far. With the fog so thick around them, the ocean sounds so much closer, leaving Caroline to keep threading away from the reverberation of waves constantly crashing. As if they will reach up and take them at any given moment.
"Damon spent a hundred and forty-five years chasing after Katherine," she says suddenly. "But I wonder, what did you do with all that time?"
Stefan, momentarily taken aback by the question, halts his step.
"Um," he starts, craning his neck and scratching the back of his head. "I went places. You know, did things."
"Wow," she deadpans. "Your ability to regale is astounding."
"Are you just asking, or do you really want to know?"
So he does. Everyone he's ever met, everywhere he's ever been. Strange little details he thought long forgotten popping up as he carries on through the decades. Somewhere around the thirties her hand reaches for his, walking at an even pace, he doesn't object.
He tells her things Damon would never think him capable of. Things he never thought to share with Elena. Things she probably never wanted to know, but the floodgates have opened, and his whole ludicrous life comes pouring out.
Neither are sure just how far they've walked when he runs out of words, but both realize something new has just built between them. Trust, while always there, can now be defined as complete. No one will ever know him like she does.
The kiss happens because that's all there is left to do.
A couple hundred miles past absolute nowhere Wyoming, when a tire blows. The spare turns out the be flat and useless, leaving them stuck on the side of some back road where no cars pass in the ensuing hours. Of course it begins to rain the second they finally agree to set out on foot, and of course they'd gotten rid of those hideous rain slickers the second the fog let up back in Oregon.
Sitting in the car, watching drops pelt the windshield, daylight is quickly running out when Caroline states the obvious.
"We can't sleep in here."
Stefan knows this. They discovered that fun fact trying to save a couple bucks somewhere in New Mexico. Only the driver seat leans back far enough to sleep comfortably, but in doing so, cuts the back seat in half leaving no room for someone to curl up. Wiping the window down, he peers out at the rain soaked countryside, looking for anything that could offer shelter.
"I think there's something out in that field," he says after a moment.
"I don't know. A barn maybe."
"Is there a house? We could be trespassing on someone's farm or something."
"No house," he replies looking over to her. "But it seems like it's our only option."
Caroline takes a second to think.
"If you're scared of spiders don't be. They tend to shy away from dead things."
"So not helping."
Even though the structure, which is indeed a barn, is only a few hundred feet back from the road they get soaked on the run. Caroline's teeth start to chatter instantly, Stefan shivers too, as he starts looking for something to start a fire with.
"Are you sure we're not just going to burn this place down?"
"Fire pit in the middle of the floor," Stefan calls from a far corner. "I think this might have been someone's drug paradise. There are homemade bongs and zigzag wrappers everywhere."
"Spend the night in burnout central," Caroline sighs. "You sure know how to show a girl a good time."
He comes back with a bundle of broken wood pieces, which he makes into a teepee in the shallow hole dug into the middle of the ground.
"Lucky for us these stoners were smart enough to not want to freeze to death out here."
Hours pass, as they huddle up close, their clothes finally starting to dry on a makeshift rack. Flames flicker and crack, making shadows dance on the walls, as Caroline's lips press into his neck.
"Admit it," she says softly. "This was all some elaborate plan to get me in my underwear."
Chicago. Always the end destination in his mind, he's still a little disappointed the road couldn't last forever. Caroline drops her bag next to the couch, running a hand through her hair, and taking a cursory look around. It doesn't take a genius to see she's not as nostalgic about their travels.
"Tell me the shower works," she says, tone inflecting that any answer other than yes will be unacceptable.
"Yeah, the building owners and I go way back. Everything is up to par."
"Thank god," she mutters, shedding her shoes and jacket. "Now where-"
"Through that doorway," he interrupts, pointing in the direction. "Second door on the right."
She makes way without another word, as Stefan gathers her things and sets them neatly next to the coffee table. Settling down on the couch, his lets his weary head fall back, a grin spreading in his lips at the sound of the water kicking on.
He takes her to all his favorite places, a sort of underground tour of the city he loves.
There's the street corner where he once punched out one of Al Capone's enforcers. The Harrison Street bridge where he kept that kid, who ended up pitching for the Cubs, from jumping. And all the spots where the speakeasies he frequented so often are long gone.
Caroline is a good sport about it, even though she finds most of the empty lots where something once stood a total bore, but then he takes her to a place that fought off the passing of time. All polished wood and mirrored walls. Music that's only played live, and liquor served smooth and easy.
They spend most of the night with whiskey neat, slow dances to a moaning saxophone, and kisses in booths lit by red lamps.
She nods off against his arm on the taxi ride home, and he carries her up the stairs even though she isn't that drunk. (Part of him assumes the request was just to see if he'd do it at all.) Laying her on the bed, he brushes stray locks of hair from her face, smiling at the way she shifts into his touch.
He's made many bad decisions. Countless with intention for the good of others. The one asking her to come with him, a rare feat of complete self motivation, acting on instinct for his benefit alone.
"Hmm?" Comes her sleepy reply, eyes never opening.
"I'm glad you're here."