Disclaimer: 'Gossip Girl' belongs to Cecily von Ziegesar, Josh Schwartz, and the CW. No copyright infringement intended.
Characters/Pairings: Nate/Serena, Blair/Dan, Blair/Chuck
Warnings: death of a minor character, some sex, drug, alcohol use by minors, alternate universe.
Summary: “They’re giving me a roommate,” she huffs, unwinding her scarf from around her neck, leaving her beret perched slouchily on her blonde hair.
It’s halfway through sophomore year and Serena van der Woodsen is about to meet her new roommate.
Author's Note: This is the fic that wouldn’t end. As always, thanks to my bb kaitoujeanne for the beta.
Dan Humphrey isn't sure what he expected from his Waverly roommate, but Chuck Bass was definitely not it. Chuck Bass is not a Lacoste wearing, beer swilling, frat boy prep (although he certainly seems to embody some of those attributes,) nor is he a band kid there on scholarship, or a goth (although Dan's not even sure that stereotype exists anymore, let alone at boarding school.) No, Chuck Bass is... exactly what he left Manhattan to get away from, but to the nth power.
Chuck Bass, to put it simply, is a rich kid.
Dan-- not so much. And Chuck's not going to let him forget it, if the expensive bottle of scotch on the wall shelf is any indication.
The tumblers next to it are probably worth more than the entire contents of his luggage.
"At least in Brooklyn it was kind of cool to be poor," he sighs, lying down on his unmade bed. His mom sent him up with plaid sheets that she and Jenny had picked out, but it seems like far too much energy to make his bed right now when he's about to endure two and a half years of living with some rich creeper with more money than sense if the bowties and bongs arranged neatly in the open closet are any indication.
There's two pictures on the mantle, one of a impossibly blonde family and a hawk nosed kid at Christmas time, and one with two gorgeous blondes and a mischievous looking brunette with the same hawk nose. He's suspecting the devil-looking kid is his roommate, a fact only confirmed two hours later when a hawk nosed fellow in a bow-tie and Waverly blazer walks in looking like Satan himself.
Dan's unpacked his meager possessions, and never has he felt so poor, not even at St. Jude's than when this guy walks into his room and says "So you're the scholarship kid they're forcing me to room with."
Chuck doesn't even look at him, just gives a dismissive look at his half of the room and elegantly tosses himself onto his bed (covered in thousand thread count sheets, no doubt.)
"That's me," Dan says, somewhat annoyed.
"Midyear transfer, so your parents are either divorcing or you got into drug trouble, but you're on scholarship, so I'm going to go with parents are divorcing."
"Something like that," Dan stammers. This kid is good.
"Hardly. Mom's dead, Dad remarried. Got a lovely blonde built-in family when I was eight, so I never have to worry about what I'm missing out on. Probably just divorce guilt presents, but I have more money than God as it is."
"Don't you mean your parents do?"
"Mommy died and left me all her money, silly scholarship child. You'll learn." Chuck sits up momentarily, to grab a pack of cigarettes off the desk and light one.
"Do you mind?"
"They let you in for your writing portfolio, I would've figured you smoked."
"You smoke, you just don't want to admit it to me," Chuck says, blowing out even rings of smoke.
"I'm not going to now that you just did that."
"A prostitute in Minsk showed me how when I was seven. Probably the reason my dad got remarried. Can't have Daddy's heir running around with prostitutes and learning how to smoke at the tender age of seven."
Dan has a skeptical look on his face.
"I was in between nannies, and dad was banging the secretary. The intern he assigned to watch me ended up fired for taking me to a brothel."
"Is any of this true?"
"Write it in your first novel, and we'll see if I sue. Then you'll know."
“Um, sure,” Dan says hesitantly. “So… what do people do around here for fun?” he asks, then winces. Why did he ask this arrogant kid that? There’s no way their definitions of fun are even remotely close.
He’s saved, however, by a blonde head popping around the doorframe.
“Chuck, do you have that—oh, hello, you must be the new roommate,” the blonde says in a bubbly rush.
“And you must be a member of the blonde stepfamily. Charmed I’m sure,” he says, hoping he hasn’t put his foot in it.
“One blonde stepfamily member coming right up,” she says, smiling. “I’m Serena.” She holds out her hand, walking into the room.
“Dan. Dan Humphrey,” he says, shaking her outstretched hand.
“Dan’s from Brooklyn,” Chuck interjects.
“No one asked you, darling. Do you have that thing that Nate gave you to give me?” she asks, looking annoyed.
“Your pot? Yes, yes I do.”
“Chuck,” she whines.
“Humphrey’s good,” he says. “Besides, while he might end up snitching on me during his time here, a move he will surely regret,” Chuck gives Dan a pointed look then continues, “he’s not going to snitch on the most beautiful girl he’s ever seen. Besides, he looks like the type to smoke some LSD or something mind-bend-y. He’s an author, sis.”
“Speaking about me like I’m not here is not the way to my heart.”
“No one wants your heart, Humphrey, just your silence,” Chuck says, blowing another ring of smoke.
“No one’s impressed by your smoke rings, Chuck,” Serena says. “Do you have it or not? Blair’s never…”
“Why didn’t you say it was for the lovely Miss Waldorf?”
“Because you would’ve been a perv like that and insisted on coming along to our girl’s night.”
“But of course I’m coming.”
“Gross,” Serena says. “If you stay here, I will give you some cookies, okay?” she nods her head along with her half-question.
“She doesn’t want to smoke for some reason.”
“I’m surprised she’s okay with the calories. She barely ate at dinner,” Chuck comments with a slight wrinkle in his forehead.
“Maybe she just doesn’t like pizza, Chuck.” Serena shrugs.
“Isn’t it un-American to hate pizza?”
“Yes,” Dan interjects.
“See, sis, the common man agrees with me that it’s un-American to hate pizza, therefore she is dieting and won’t want cookies.”
“Argh, Chuck. Just give me it and leave my poor roommate alone! Go play Halo with Nate or something. I’m not going to vaporize because you have mine and God knows what you did with it last time.”
He tosses her a bag and gives her a salute.
“I could tell you that it involves--” Chuck starts.
“Thanks,” she interrupts, stuffing the bag in her purse. “Dan, it was nice to meet you. Don’t let my stupid brother upset you too much.” Serena gives him a smile and leaves, quietly shutting the door behind her.
“Well, I think she had the right idea,” Chuck says. “Have fun. Don’t do anything I wouldn’t do,” he says, getting off his bed and moving to the door. “I’ll be playing Halo if you need me, which you won’t.”
Dan groans and leans back against his pillows. A whole term with this wacko? He’d rather be in Hudson.
Blair is surprised when her mother calls after she’s been there three days. It’s rare for Eleanor to check in. She usually left all of that to the nanny or Blair’s dad, but they’re both in France. With each other.
Blair’d think it was cute if they didn’t leave her behind to her fate.
“School’s fine, Mom,” she sighs. “It’s a school. The academics seem to be as advanced as Constance, so Yale shouldn’t be an issue. In fact, none of the sophomore girls look like too much competition. My roommate doesn’t want to go to college,” Blair laughs. “Can you imagine that? But she’s a legacy at Brown.”
“Just be careful who you associate with, Blair,” her mother warns. “While you’re at it, my business partner, Bart, has a son there.”
“Mom,” Blair whines.
“It’ll be advantageous, Blair. Now, his name is Charles. Charles Bass. He has a stepsister named Serena but they don’t always get along from what I hear. She’s a bit of a flighty girl, from all accounts.”
“…Chuck Bass? Serena Van der Woodsen?” Blair asks in an incredulous tone.
“Well, yes, Blair,” her mother says, sounding surprised. “I see you’ve already done your homework.”
“More like you have, Serena’s my roommate,” Blair says, sounding disgusted. “Chuck’s already asked me to go to some weird party with him.”
“Well there, you see, Blair? You’re already fitting in.”
“I said no, Mother, like I’d go to a party with that jerk.” She pinches her nose. She doesn’t usually talk to her mother like this, but the red wine last night with dinner and those cookies that she was too stoned to throw up are making her head pound.
“Now, Blair, this is important that you try to get along with them.”
“I like Serena, isn’t that enough?”
“Blair, if this deal falls through, we won’t be able to afford Waverly since your father drained all the accounts before his little jaunt to Europe.”
“Daddy would never!”
“I’m sure he has a reason, Blair, but until we can get a hold of him, this deal is the only thing keeping you from public school, so play nice.”
“Yes Mother,” Blair says. She hangs up the phone and takes two ibuprofen before she leaves for her campus tour. Hopefully she can hide behind dark sunglasses the entire time.
They're being shown around Waverly on his second day there. It was called a mandatory new student orientation, but as far as Dan can see, it's him and one girl being shown around by the junior class prefect, a bored pretty girl with a perfectly pressed blazer hidden underneath her thick wool coat. The other new kid, Blair, has been very quiet on their tour around campus, nodding occasionally in response to a remark. Her eyes are hidden behind a dark pair of sunglasses, almost identical to Audrey’s in Breakfast at Tiffany’s. He guesses she’s the Blair they were talking about last night, which would explain the sunglasses.
The tour is like any other campus tour that Dan's been on, boring and vaguely informative. His mother liked to make a habit of touring college campuses when they were on tour with his dad, so he's been on his far share of tours.
But the tours dried up a few years ago, and Rufus started selling art instead of music, and Dan wasn't forced to go on any more campus tours.
It's a wonder they didn't ship him and Jenny off to boarding school years ago, then Dad might have stayed on the road.
"And this is the soccer field," the junior class prefect announces suddenly, even though it's quite obvious to anyone that it's a soccer field, even with the snow covering it. "Dan, it says here you used to play soccer?" she queries.
"Uh-huh," he replies. "But I didn't know you had a team here?"
"Of course! Obviously they practice indoors at the moment, but they're quite good. They’ve set up a walk-on tryout for you tomorrow after classes in gym A, which I'll point out as we pass. Waverly just wants to encourage all our transfers to stay involved in activities."
"Great," Dan says. Soccer again, doesn’t sound like he has much of a choice. Still, it might be a way to meet kids other than his toolbox roommate.
Blair seems nice though, even if he’s only said two words to her.
She takes another sip off her coffee that she’s been clutching for most of the tour as he watches.
“So what made you decide to come to Waverly?” Dan asks Blair. Their tour guide has stopped to flirt with some boy about ten feet away, instructing Blair and Dan to ‘take in the academic excellence that will be their home from now on.’
“My mother thought it would give me a better shot at getting into Yale,” she says lifting her sunglasses to rest on her head. “You?”
“Divorcing parents, you know the drill.”
“Mmm,” Blair says, noncommittally.
“So, Yale, huh?”
“I’ve wanted to go there since I was a little girl,” she says.
“Like Rory Gilmore.”
“That was Harvard, ugh.”
“But she ended up at Yale.”
“So? She still wanted to go to that… ugh.”
“Not that I disagree, Yale is clearly the superior school,” Dan says.
“Don’t tell me you want to go there too?” she asks, squinting at him in the sudden winter sunshine.
“Argh, no. Not here, that’s why I came here!” she says, stamping her foot. “What classes are you taking?”
“It’s not a big deal, people can get into Yale from the same school.”
“It is a big deal! I left New York to get away from that bitch of a best friend who was dogging my every move to get into Yale before I did.”
“And why does this sociopathic outburst make me anymore likely to show you my school schedule?”
“Because otherwise I will destroy you. I know where you’re going to be tomorrow, remember?”
“Fine,” he huffs. “But you have to agree that more than one person, especially people of different socioeconomic statuses and backgrounds, can get into Yale from the same school.”
“I suppose it might conceivably happen at some point. Or you could just transfer to St. Andrew’s for your senior year,” she says, pulling her class schedule out of an oversized purse that doesn’t really fit with the rest of her outfit. “Now, let’s see.”
She purses her lips as he hands over his schedule. “Good, we have English together. And Chemistry. And history. And pre-Calc. What was your GPA?”
“Ugh, weighted averages.” Blair makes a face. “Meet your new study buddy,” she says, holding out a gloved hand.
“It’s nice to meet you, Miss Waldorf,” he says jokingly, kissing her hand.
She smiles at the display of chivalry, and he’s pleased he read her right.
“So,” he remarks, “do you think our tour guide will be finished flirting anytime soon, or will we have to make a break for it?”
“My, Daniel, what crazy ideas you have in your head. Perhaps we should go wait for her in the library.”
“ And discuss contemporary literature?” Dan asks, a hint of hope in his voice.
“Today seems more like a day for depressing Russian novels by the fire,” she says.
“That’ll certainly warm the heart,” he quips, and holds out his arm for her to take. “Shall we?”
“Let’s shall,” she says, taking his arm and smiling up at him.
“How was your tour?” Serena asks, glancing up from her magazine as Blair waltzes in. She’s humming, which is something Serena hasn’t seen from her before.
“What? Oh, good,” Blair says, sitting down to take off her boots.
“You see all the sights? Scope out some boy watching spots?”
Blair blushes, and Serena knows she’s hit on something. “Meet any cute boys?”
“Serena!” Blair yips.
“What was his name?” She inquires, reaching up to her desk to grab her lemonade. Blair sighs, her eyes watching Serena take a sip.
“Oh, Chuck’s new roommate? He’s cute. Don’t worry, you can have dibs.”
“Yeah, like… Oh, Georgie always called them but never respected them.”
“She doesn’t sound like a very good friend,” Blair says, scrunching up her nose in distaste.
“She’s just free spirited. Whatever, tell me more about Dan.”
Nate's stretching, watching as the freshman on JV run around. He’s already varsity, and fast tracked to captain next year. So he’s here, stretching, waiting for one Dan Humphrey to show up. He can’t leave either, his academic scholarship being pitiful compared to his soccer scholarship. He doesn’t mind completely though; he needs scholarships for college and the sooner he gets used to jumping through hoops not set by his grandfather, the more he jumps through hoops of his own choosing, the better for him in the long run.
This Dan Humphrey isn’t making the best impression, though. He’s already ten minutes late.
“Sorry, so sorry,” a breathless voice calls out behind him. “I had trouble finding the pitch.”
“Mmm,” Nate says. “Dan Humphrey, I presume?”
“That’s me,” Dan says, holding out a hand for a shake.
“So, why do you want to play for Waverly?”
“They’re kind of forcing me to tryout as a condition of my scholarship,” Dan says, shrugging.
“Yeah, usually the academic scholarships are pitiful compared to the sports ones. You play at your last school?”
“Yeah, as a defender.”
“Nice,” Nate says. “You ready for me to put you through your paces? Show you some of the ropes?”
Dan shrugs. “Sure, why not?”
Nate kicks the soccer ball over to Dan, and they begin to scrimmage, testing out Dan’s skills.
“Whew,” Nate says, taking a chug off his water bottle. “Not bad, I think I can safely say you’ve made the team.”
Dan smiles and takes a swig off his own water. “It’ll be nice to get out and meet some new people other than my toolbox roommate.”
“Well, why don’t you come to the barn party on Friday night too? That’ll help you meet some new people that aren’t dudes.”
“I’m not much of a party person,” Dan says, hesitant.
“It’ll be fun. I’m going, my best friends are going, and my girl friend just got a new roommate so you can meet someone else new too.”
“Well, okay,” Dan says.
“Great,” Nate says, clapping Dan on the back. “Welcome to the team, buddy.”
Chuck left her a note on their whiteboard as she’s getting ready for the party.
“BLAIR WALDORF: WILL YOU BE MY DATE? CHECK YES OR NO”
But there’s only a yes option.
“That’s my stepbrother for you. He maybe doesn’t deal so well with rejection,” Serena says, putting on a pale pink lipstick and making faces in the mirror.
“Is Nate picking you up?” Blair asks, smoothing a red color over her lips. It’s unfair how little makeup Serena can get away with and still look stunning.
“Nah, why would he? We’ll run into each other there, I’m sure.” Serena throws her keys into her pants pocket, then shakes her head as Blair picks up her purse.
“Leave it here, you’ll only get it stolen if you take it. Just take your cell in a pocket in case we get separated.”
“I don’t have any pockets,” Blair says, looking down at her outfit in dismay.
“Then tuck it in your bra. Here,” Serena says, putting the phone in the hollow between Blair’s breasts. “Good thing you’re not wearing an ultra-push up, those are impossible to fit phones in.”
“This is weird,” Blair says, peeking down at the phone in between her breasts.
“It’ll be fine, come on!” Serena exclaims, grabbing Blair’s hand and tugging. “If we get there early, we can drink most of the keg before anyone else gets there.”
“But I’m not finished with my kamikaze you made for me,” Blair says. Serena picks up the glass and drains it, then resumes tugging.
Blair takes a last look at the empty glass before letting her roommate pull her out of the room.
It’s still light out when they get there, barely, and Blair watches them set up with amusement.
“We had to rush down here for this?”
“Shush, I’ll be right back,” Serena says, and Blair watches her roommate flirt with everyone in sight and return with two full beers and a sack of weed, without any money exchanged.
“Um, wow,” Blair says, and Serena hands her a beer.
“You’ve got it too, if the scene at the pizza shack last weekend is any indication.” Serena hops on to a hay bale and takes a sip of her beer. “It’ll be mellow for a while, but Chuck and Nate are coming. Chuck’s new roommate too.”
“I didn’t realize Chuck and Dan were getting along,” Blair remarks casually.
“They’re not. Nate and Dan are.”
“Oh?” Blair asks, intrigued.
“They’re on the soccer team together.”
“Dan didn’t mention anything this week about that,” Blair says, blushing slightly.
“Oooh, someone knows Dan super well now huh,” Serena says, giving her a shoulder nudge. “I guess he doesn’t really want to talk about it? That’s the sense I get from Nate.”
“And how are you and Nate?”
“Ugh, same as always. Why do you always make us sound like a couple?” Serena wrinkles her nose and drinks the rest of her beer. “Wanna come with me and get introduced to all these guys?”
Blair hesitates. “I think I’ll just stay here for a while,” she says, leaning against a hay bale and trying to look cool.
“All right,” Serena says. “Text me if you need me.”
Blair nods as Serena walks away into the sunset. Great. Her first Waverly party and she’s already all alone.
Nate nods to several people as he walks up to the empty field. It’s still early, but Serena always shows up five hours before any party with a keg just to drink the majority of it herself. This time he wants some beer himself.
“So, this is the field,” he says to Dan. “Impressive, huh?”
“Uh, yeah. Do they have a lot of parties here?”
“Yeah, the abandoned barn and this field is technically off school property, so we can’t get in quite as much trouble from school if they catch us, although they mostly turn a blind eye,” Nate says, then watches as Serena swans over.
“Hi boys,” she greets them, a red plastic cup in her hand. She leans over to give Nate a kiss on the cheek, and shakes Dan’s hand.
“I know we met before Dan, but it’s nice to meet you again under less filled with my stepbrother circumstances,” Serena says. “Blair’s around somewhere, you should find her.”
“That’ll be nice to see a familiar face,” Dan says, then backtracks. “Not that you two aren’t familiar too, but Blair and I have classes together. I mean, more than I have with you, Nate.”
Nate laughs. “Relax, man. Drink your beer, it’ll help.”
Dan looks unsure. “Maybe I should just go home.”
“Stick with us,” Serena says. “You’ll do fine.”
Blair is still against a hay bale, her untouched cup of beer resting next to her.
“You never answered my note, Blair,” Chuck drawls, running a finger down her lapel.
“Why would I answer your booty call, Chuck?” she snorts, stepping away from him and straightening her lapel. “We’re not anything.”
“Maybe I want us to be.” He’s uncomfortably close again, backing her up against the wall of the barn.
“What do you think of your new roommate,” Blair asks desperately, as his hands are in her hair and his mouth is close enough to smell the cheap whiskey he keeps stashed under his bed.
“Dan?” Chuck pauses, smirks. “You have a crush on Dan?”
“I don’t have a crush on anyone, Chuck, least of all you.” Blair pushes roughly out of his embrace. “Just stay away from me, please. You won, okay? You won your bet with Nate, so just leave me out of it.”
“It wasn’t a bet,” Chuck says.
“Just leave me out of it.” She’s shivering, her arms around herself.
“Go warm up by the fire or drink some of this,” he says, handing her his flask.
“I’m not cold. This party is stupid but Serena has my keys,” she says, accepting his flask. Several swigs later, she hands it back and takes a sip off her warm beer.
“Thank you,” she says primly.
“It’s okay to loosen up a little, Blair,” he says, tucking a strand of hair behind her ear. “It’s a party.”
“A very cold party,” she remarks. He hands her his jacket, and she puts it on with a nod of thanks.
“I can warm you up,” he smarms, and she laughs, but doesn’t push him away.
“Do your worst, Chuck Bass,” Blair says, and isn’t surprised when he leans in to kiss her.
School falls into a comfortable routine for Blair. She goes to class, studies with Dan, drinks full-fat hot chocolates with whipped cream on top with Serena and smiles politely at her teachers. Chuck is ever-determined to make her his girlfriend and devirginize her, or maybe just devirginize her, and passes her notes in every class they share. She pretends not to notice when Dan glares at Chuck. Secretly she’s thrilled. She’s never had one boy interested in her, let alone two.
Three weeks after they start classes, Chuck flicks Blair a note in the middle of English. It reads, "Help me, Waldorf, you're my only hope."
Blair smiles a little, despite herself, then smoothes out the piece of paper and sticks it under her books.
"Star Wars, Bass?" she says as they exit the classroom, her books tucked neatly under her arm. Chuck's simply got a worn paperback copy of Moby Dick, spine creased from thousands of readings.
"Eric liked it, possibly a little too much."
"Stepbrother. Didn't Serena tell you?"
"She's mostly got pictures of you and Nate on the walls, honestly. She's said a little about her younger brother, but she mostly keeps him to herself."
"Strange, they've always been closest. I love the kid, but they have some weird freaky twin bond going on. Probably from growing up with Lily."
"Mmm," Blair says noncommittally.
"It probably would've been the same if I'd had a sibling," he says wistfully.
"Well, now you have two, that you seem to get along reasonably well with, which is more than I have. Mom let Dad take my cat when he ran off with the nanny." Blair twists her mouth, then looks up at Chuck. "I don't have anything."
"You've got Serena, and those terrible textbooks that you cling to in the middle of class when I so desperately need your help, Waldorf."
"And what do you need my help with today, Charles Bass? Alleviate your boredom? Plotting world domination? Econ homework?"
"Please, we both know I can run rings around you in Econ."
"Just because your dad's a famous businessman and you've been learning it from the cradle does not mean you're better than me."
"Oh Waldorf, how little you know,” Chuck says, holding out his arms for her books. She blushes and letting him take them as he walks her towards pre-Calc. “You looking forward to your field hockey tryout tonight?” he asks.
“Don’t remind me,” Blair says, lightly swatting his arm.
Serena and Blair trudge back from the field, sweaty and disheveled, their field hockey sticks perched jauntily on their shoulders. Chuck smirks as he passes, calls out:
"Looking good, van der Woodsen!"
Serena rolls her eyes at her stepbrother and ignores him.
"So," she says to her roommate. "How'd you like it?"
"I liked it, I just don't know if I was good enough." Blair stops to adjust her stick on her shoulder, then continues walking. She's trying very hard not to look back at Chuck.
"Please, Blair, even if you weren't good, I'm captain next year. You'll get on the team." Serena pauses next to Blair, then turns to look at Chuck, who's still standing there watching them walk.
"I think my stepbrother has a crush on you," she casually remarks.
"Please, the only thing Chuck has a crush on is himself," Blair says, but her cheeks turn pink.
"Mm-hmm," Serena says. “Anyway, the season’s almost over, but it’ll be good to have you practice with us. Then next year we can kick butt.”
“Kick butt,” Blair says, her tone light. “What are you, five?”
“Yes, in fact,” Serena says, grinning.
“I have never had a friend like you before.”
“And you never will again, Blair Waldorf, I’m one of a kind. Now are you going to help me plan pranks on my stupid stepbrother or do I have to enlist Natie who is always a spoilsport?”
“Oh, I’ll help, I owe him for getting me a detention with his stupid note passing. But instead of Nate, what do you think about Dan?” Blair suggests, a sly smile on her face.
“Dan? New kid Dan? As in Chuck’s new roommate, Dan? Oh Blair, you are too perfect,” Serena says, dropping her field hockey stick and throwing her arms around Blair.
“You’re sweaty,” Blair remarks, but returns the hug.
“So’re you, princess!”
“Don’t call me princess.”
Serena rolls her eyes at Blair, sticking her tongue out.
There is a tangible relief for Blair, settling in at Waverly. Yes, she and Serena are not the most popular girls, but she finds herself wanting that less and less. They’re not unpopular, and they are only sophomores. She doesn’t miss ruling over Constance with an iron fist, or the minions, or the constant worrying about how Nelly was going to backstab her. Here all she has to worry about is whether Serena borrowed the pair of shoes that match perfectly with her outfit without asking.
Well, that and Chuck Bass.
He hits on her friends (except Serena, obviously,) and is mean to Dan. He leaves her annoying messages on their whiteboard and passes her notes in class. Once, he leaves her a bouquet of poison ivy—she doesn’t know how he got it, but the message is clear.
Serena just shrugs. “He’s never really gotten beyond the whole pigtail pulling method of courtship.”
“Courtship?” Blair raises an eyebrow.
“He’s never liked a girl this much, B. Most girls don’t last more than a night with him.”
“What about your… friend?”
“Georgie? Oh no, they hate each other.”
“I hate him.”
“It’s very different B. They hate each other hate each other.”
“How is it different?” Blair insists, fiddling with the edge of her bedspread.
“Georgina’s… like a female Chuck, in that sense. They can’t stand that they’re both trying to play each other and they can’t respect it. You know, that whole, ‘don’t play a player’ thing.”
“…uh, I guess that almost makes sense.”
“They’ve never gotten along. Although, they did make out that one time they tried E for the first time.”
“I’ve never tried it.”
“B, I’d probably make out with Chuck on E and everything else they were on.”
“Don’t you dare.”
“Oh, so someone does have a little crush on my stepbrother!”
Blair glares at Serena. “Jerk. Just because I made out with him one time.”
“One time? Blair, it was your first kiss!”
“So?” she huffs. “That doesn’t make up for all the courting he’s not doing now. Besides, he probably lost his virginity to that girl.”
Serena is silent, which confirms Blair’s suspicions.
“Ugh,” Blair says, flopping back on her bed. “I knew he was more experienced than me, but really? I don’t even know her and I hate her.”
“B, you should just go talk to him about it,” Serena says. “He really doesn’t like her that much, and we both know he’s into you.”
“Fine,” Blair says, smoothing her skirts as she sits up. “But I want hot chocolate when I get back.”
“If you get back,” Serena giggles, and ducks the pen Blair throws at her head.
“Come in,” Chuck calls at the tentative knock on the door. It’s not Nate, and Dan’s been out all afternoon. Perhaps it’s a freshman come to seek wisdom, or an upperclassman to threaten him with bodily harm if whatever he’s blackmailing them with this week comes out.
Or, better yet, it’s Blair Waldorf.
“Finally come to answer my booty call? Darling, I’m thrilled.”
“Why didn’t you tell me you lost your virginity to Serena’s old roommate? Then I could’ve known it was just some obsession you have with fucking your sister’s roommates instead of actually thinking you liked me.”
Chuck pauses at Blair’s outburst and considers his next words. She’s shaking and tapping her foot, looking impatient, which automatically puts him on the defensive. “I don’t owe you anything Blair. But I will say that Georgina is a girl, one of many that I didn’t care about from a time period before I even met you.”
“You want me to be your girlfriend, yet you won’t even be honest with me about some girl you claim to care nothing about? God, Chuck, what am I supposed to think? Everyone’s warned me you’re a player, I should know better.” She shakes her head, her curls tossing with the movement.
“But you’re just a shy little virgin who wants to believe the best in people,” he says mockingly. “You’re as calculating as I am.”
“You don’t know me,” she huffs.
“You’re not going to go back to your room yet, you’re going to go hide in the library so Serena doesn’t see you cry. Admit it.”
“I’m going to the library to study and to get away from you, so you can go tell your stepsister what a jerk you are.”
“You’re the one that barged in here all full of questions about my past, Blair,” he says tiredly.
“Then I’ll leave,” she says simply. “Sorry for thinking this could be something.”
He stares through the door long after she’s gone.
Serena’s bored. She’s braided her hair five times, flipped through last month’s Vogue, taken two swigs off Blair’s secret gin stash, tried on all her shoes, and read ahead two nights of reading. So it’s not entirely surprising that she opens the door to Dan Humphrey when he knocks, even though she knows that the dorm mistress is out for her blood.
“Dan,” she says, smiling. “Come in,”
“I uh, can’t stay long,” he stammers, and she smiles wider, a little like the Cheshire cat.
“Of course you can,” she says, waving her hand expansively. “Gin? Gin Rummy? Both?”
“Is Blair around?” he says, perching on the edge of Blair’s immaculately made bed. “I wanted to compare chemistry notes.”
“You know you’re not allowed in here,” she says, pouring herself a glass of gin. Might as well, it’s not like she has any homework left.
“I err, that is, um…”
“Oh relax. I don’t bite. Hard.”
“That’s uh…” he stammers, and Serena bursts out laughing.
“So you and B have chemistry together, huh?” she asks, pouring him a glass without asking and sliding it down her desk towards him. He gulps, his hand hesitating over the glass.
“Er, thanks. Yes, we do. And history, and English.”
“You both in world lit?”
He nods, taking a sip of the gin and feeling the burn down his throat.
“Oh, I think I have tonic water here somewhere,” she says absentmindedly, and sets her glass down to start digging in her closet. “Let’s see, Louboutins, Dior pencil skirt, notebooks from last year, absinthe, oooh absinthe, do you want to try that? My friend Georgina sent it over from Europe, she’s on an exchange there. Please say you’ll try it with me later? No one else wants to!”
He smiles at her enthusiasm.
“Why not? Writers are supposed to have life experiences.”
“Ooh, are you a writer?”
“Aspiring, although I suppose I’m supposed to say I’m a writer either way. But I haven’t written anything very good yet, certainly nothing publishable. Not enough life experience, I guess.”
“Psh, life experience is overrated. The classics are all half scenic descriptions anyway,” Serena says, pouring them both a heavy glass.
“Aren’t you supposed to add water?” Dan asks nervously. She’s gorgeous, pouring the alcohol and humming a happy song as she searches for sugar.
“Hmm? Oh yeah. I’ll get some in a second,” she replies, triumphantly brandishing a lighter. “Why this was in one of Blair’s shoe boxes, I’ll never know.”
“I’m surprised she hasn’t killed you yet. Blair seems a little OCD about things.”
“For some reason, she puts up with my flightiness. Probably because I drug her.” Serena giggles at her own joke, and pulls out a box of sugar cubes from an underwear drawer—whose, Dan does not know.
“Now,” she says, rubbing her hands together eagerly, “it’s time!”
“Water?” Dan croaks. She looks like an evil (crazy hot) mad scientist as she pulls out a Brita pitcher from the mini-fridge and adds water, then flaming sugar cubes to their beverages. The Dandy Warhols play over the speakers, and he does want to be Bohemian Like Her in this moment.
“How appropriate. Georgie says this is the bohemian method of making it,” Serena remarks as she takes a sip. He grimaces as he takes one, he’s never much been one for hard alcohol even though it’s what all the famous writers did. He’s no Hemingway though he thinks she could be Agnes because it’s likely she might break his heart.
She sighs, and the sounds of her breathing and the music intertwine as things swim in and out of focus.
“This isn’t like being drunk at all,” she remarks from her spot on the floor, her hair fanned out around her. “It’s more like I’ve drank too much Nyquill.”
“Mmm,” he says, picking up a hunk of her hair and examining the way it shines.
“It’s…” and instead of finishing her sentence, she scoots up her head so it rests in his lap.
“Hi?” he asks.
“Hi,” she replies, and reaches a hand up to his neck.
“Is Blair—I mean, will Blair be back soon?” he asks nervously, his face inches from hers.
“Does it matter?” she murmurs, then presses their lips together.
No, it apparently doesn’t really matter, because he gets a little into it.
Blair collapses onto Serena’s bed at midnight. She fought with Chuck and then hid in the library for four hours, in which time Serena managed to down most of a bottle of absinthe from the looks of it.
“Serena, why are you in my bed?” she asks, sighing.
“I’m in my bed, aren’t I?” Serena replies. “No, I am in your bed. Also I made out with Dan, but I really think he likes you. Why is your hair so pretty? Where have you been? Making out with Chuck?”
“What? What are you talking about, S?”
“Dan likes you, did my stupid stepbrother tell you that he likes you too?”
“If Dan likes me then why did he make out with you?”
“Absinthe, probably, B, but he did say your name in the middle of our make out session and then I kicked him out. I don’t think he even realized what he said, he was that drunk. Tell me what happened with Chuck.”
Blair squints at Serena in the darkness. “How drunk are you?”
“Not very, it’s just strange now. I was very,” Serena says. She pats the bed beside her. “Come over here and tell me what happened with Chuck.”
“Pushy,” Blair says. “That’s supposed to be my domain.”
“I learned from the best,” Serena says, moving aside to let Blair climb under the covers with her. She tucks them in as Blair begins to recite the night’s events.
Daniel Humphrey isn't sure what to expect of Waverly. His dad has shipped him off here while his parents’ marriage is falling apart, and Dan isn't sure what to make of it. They're telling Jenny that it's just a temporary thing, his mother going off to Hudson to paint, but Dan knows the truth. It's a trial separation, and no amount of "Alison just needs some time to paint right now, you kids are old enough to understand that, right?" changes the fact that his mom found his dad listening to old records after they'd bumped into Lily Bass and her kid over the holidays.
Dan's not stupid, he knows his dad has some sort of weird infatuation with Lily Bass and his mother can't stand her, something from back in the days of Lincoln Hawk, but what that has to do with now, why his mother can't stand it now, doesn't make sense.
So Dan asks questions, and Dan pries, and Rufus and Alison decide he'd be better off at a school with a really good literature program like Waverly just to help him "get his mind off things."
What they don't realize, what he doesn't realize until it's almost too late, is that Lily Bass is reincarnated in her daughter, and he's about to make the same mistakes his father did. She's tall, blonde, beautiful, spirited, free, full of laughter, and he can maybe start to see what his father saw in Lily, before society trapped her into a perfect marriage with three perfect society children (well, two and Chuck Bass, but two out of three isn't terrible.) Serena doesn't seem like the perfect society child when he meets her, she is the perfect society child. She's got this mixture of impish desire to please and be pleased, and poise for days. Yes, he thinks he could imagine a future with her, even if she is Lily Bass's daughter, and the only girl guaranteed to piss of his free-thinking liberal mother.
Until he meets Blair Waldorf, that is, and everything changes.
Blair Waldorf is the patron saint of the Upper East Side, poised, graceful, bon mot tossing, intelligent, beautiful creature that transferred in this term like he did. They're in all the same classes, the same friends, she's going out for field hockey, he's trying out for soccer, they both want, believe, need to go to Yale.
It's like they created her in a lab for him. She even looks like him.
And she's sweet too, and wants to study with him, and there's something so right about her.
He'd have trouble deciding, only Serena seems fixated on Nate Archibald, and he thinks it's only a matter of time before they’re dating. She’d practically said as much when she was shoving him at Blair at the barn party. Her recent actions though… Dan doesn’t know whether she’s really as fixated on Nate as she says.
But he waits, and he plans, and he helps Blair study and becomes her lab partner, all without realizing that his roommate, the deplorable Chuck Bass, wants Blair too.
It's a stray comment that clues him in.
"Waldorf again, Humphrey? You could do better," Chuck scoffs one night as he's getting ready for a study date.
"She's the smartest girl here, plus we transferred in at the same time so we have a lot in common. What do you care anyway. Just means more girls available for you if I focus on one girl."
"I don't care," Chuck says. “You should stay away from her. She can do better than a plebe like you.”
“Thanks. How about your stepsister? She off limits too?” Dan asks, getting annoyed.
“She’d never look twice at you,” Chuck scoffs. “She’s been in love with Nate since she was ten.”
“Then why did she make out with me last night?”
The blow hits. Dan’s finally won one over on Chuck. “Later,” Dan says, hoisting his backpack over his shoulder and leaving the room.