Dean doesn't want Tessa to come and pick him up on New Year's Eve, but Mom understandably doesn't want him driving around in the Impala so soon after having his nose broken — and one of his arms twisted on Christmas Eve, but hey, who's keeping score, besides the folks who keep Dean's medical records (and who give him increasingly funny looks when he shows up with new injuries)? At least, Dean figures, Dad hasn't hit Mom or Sammy, or hasn't since Dean's been home.
The sky's grown dark and starry as Dean climbs into the passenger seat of Tessa's hearse — for which he sometimes calls her Maude, as in Harold and Maude, her favorite movie since they were twelve — to the dulcet tones of whatever opera she's listening to today. As he fastens his seatbelt, she catches him cocking his eyebrow at the speakers, and she smiles that familiar, even smile. Tucking a piece of her long, black hair behind her ear, she explains, "It's Madame Butterfly. I thought some tragic romance was a good way to send this year packing."
She pulls out onto the road and takes off down it at a speed Dean can respect — though he's sure the cops, if any of them are out tonight, will take some kind of fucking issue with the fact that she's going fifteen over the speed limit when it's cold outside. "…You know that they're singing in Italian, right?" he finally asks.
"At the performances I've been to, they generally have translations flashing above the stage." Tessa's face remains impassive when whips around a left turn without much regard for their safety… but, hey, there wasn't any oncoming traffic, so, even if it's odd for her, it's not as though she cut somebody off. "More importantly, though, you don't need to understand it literally. Opera's all about the feeling."
For all he's heard that same explanation before — and for all he still doesn't really get her meaning — Dean guesses that she's got a point, since the soprano singing now might not be a Joan Jett or an Ann and Nancy Wilson, but she sure sounds pretty pissed off about something. When they come to a stop sign, Tessa ruffles Dean's hair and informs him that he's cute. They trade off catching each other up on their lives at school through the rest of the tedious preparations — parking at the liquor store, buying their twelve-pack of beer (and the peach schnapps, and the Black Jack, and the two six-packs of Bacardi Silver Signature Sangria, because Tessa has an over-fondness for booze that tastes like fruity soda), telling Johnny behind the counter that they won't get caught doing anything stupid — but Dean dances around the biggest revelation until they're parked out on the old field, sitting on the hood of her car, and he's had enough whiskey and beer that Tessa's talked him into trying one of her sangrias.
"Don't knock it 'til you've had one for yourself, sweetheart," she chides him, handing over the bottle. Taking the top in his leather jacket, he cracks it open, and as he's tipping back the first sip, she lets it slip: "I can't believe you still haven't told anyone what your father does to you." He nearly chokes on his fruity drink, and with her expression sympathetic underneath the full moon's light (and that from her headlights), she concludes, "That broken nose looks nasty."
Dean shrugs. "Yeah, well… giving my dad enough time with some tequila is like giving him a fully-loaded shotgun. …Except, you know, it's his fists and nothing lethal." When she points out that, technically, fists can kill people, he cocks his head and smirks. "Maybe. But my dad won't kill me, and I'm just hoping that my face isn't still messed up when I get back to school in January." She wrinkles her nose, scrutinizing him, and asks why that is. "Because I have a boy. …I mean, I do if he'll still have me and he hasn't gone packing back to Bible camp for Christmas."
As he makes his way through this sangria and another one, he tells Tessa about Castiel and his blue eyes, and the infuriating but endearing way that he doesn't ever seem to understand people, and how crazy he is about the library and organizing his books, and how he's so stubborn but he has that air of someone who needs protecting (but not about the drugs, because he promised Cas he wouldn't talk about them) — "And it's insane, Tessa, I know it is — it has to be… but I've never felt like this for anyone before."
She pauses, and a teary look glimmers at the edge of her eyes before she tells him, "That's great, Dean, that's so… I'm happy for you."
He tilts his head and asks her, "What's up with you tonight? …The opera, the lying to me — you were driving like I do, for God's sake—"
"My dad found out," she says, her voice short and clipped; sighing, she yanks a ring box out of her jacket pocket. Inside sits a diamond engagement ring. "There was this guy up at school. He's a member of the congregation and he sort of… happened upon me and Anna. And first, he just blackmailed us — took a video of us having sex, and said that as long we didn't tell anyone about it and helped him with his homework, he wouldn't tell my dad." A sharp, sardonic smile tugs at the corner of her lips. "And then he told Dad anyway. So… now I'm engaged. To some family friend's son from Georgia… Dad really thinks this is going to fix me."
Dean says nothing, just finishes his drink and chucks the bottle at the open field. Once his hands are free, he takes Tessa in his arms and holds her; burying her face in his jacket, she hugs him back. Nuzzling the top of her head, he tells her, "There's nothing about you that he needs to fix."
Against his neck, she whispers, "Tell that to him."
"I will," Dean agrees. "I'll tell him that until he's blind and deaf."
She chuckles, but the laugh is not a happy one, the kind of laugh Dean wants to hear, and when it's gone, she says, "I hope your boy knows how lucky he is to have you, Dean."