AN: This is story is currently being rewritten but I'm leaving it in its complete state and just posting each edited chapter as I go. So far, this chapter and Chapter 2 are both updated. I'll leave a new author's note on each chapter that has been re-edited. I'm also extending the story as upon re-reading it, I realized it was rather abrupt at times. Thank you to you all that read this the first time around and we're kind enough to leave positive feedback despite the flaws in it. You guys are the best!
The sun hangs high in the sky, the warmth beating down on Blair Waldorf as she lays in a lounge chair while sipping a raspberry vodka lemonade. She sets down her drink momentarily to readjust the straps of her Alice + Olivia tropical print one-piece. Beside her, her best friend and roommate for the summer, Serena van der Woodsen is easily chatting to her about tomorrow's event, the annual Summer Kind of Wonderful soiree. At the end of every May, the van der Woodsen's kicked off summer with the festivities, always attended by anyone who mattered in the Hamptons.
This year, would be no different. Lily van der Woodsen, Serena's mother, was in a frenzy over last-minute details as was Blair's own mother, Eleanor, who was an unofficial cohost. Tonight, mothers and daughters would be joining for dinner to go over tomorrow's schedule.
"Serena, Blair!" Lily's voice interrupts their conversation.
"By the pool, Mom!" Serena calls. Serena lowers her voice to say to Blair, "As much as I love Summer Kind of Wonderful, I sort of can't wait for it to be over. My mom needs to stop bursting into our house with no warning."
"Agreed. Maybe we should change the locks." Blair muses. The small cottage they share every summer in the Hamptons allowed them space of their own and a break from their fussy mothers. Their cottage had a sprawling backyard, pool, and just about everything else they could need. Though it was hardly shabby, it was quite dainty in comparison to the van der Woodsen's beachfront mansion which would host tomorrow's event.
The girls go quiet as Lily walks into the yard. "Girls, listen to this news! I have just confirmed that Anne Archibald, if you recall my new friend from the country club, is bringing her son Nathaniel to the party." Lily's expression is positively gleeful at this development. Meanwhile, Blair and Serena share a look that says Oh no, here we go again .
Their moms trying to set them up was no unfamiliar occurrence. Over the years, unofficial arranged alliances had been formed throughout the Upper East Side families. All the moms would gather at their boozy brunches to ruminate as to whose daughter could be paired with whose son. Almost always, their choices were less than ideal.
"I've told her all about you two," Lily continues. "Of course, and she promised she would introduce you. Oh, and Nathaniel is apparently bringing a friend who is also quite eligible."
Serena rolls her eyes, "Mom you have got to stop trying to set us up! You know I want to meet someone and settle down just as much as you want me to but who even are these guys? The last guy you tried to set me up with wasn't even legal yet."
"Actually, I think I know who he is." Blair speaks up and turns her attention to Lily. "Is it the Nathaniel Archibald, who's running for senate?"
Lily nods eagerly, "Yes, the very same! Rumor has it, he's eager to find a wife. You know, politicians need to have a gorgeous wife on their arm and especially one who can deal with the public eye." She gives the girls a knowing look.
"Mom it sounds a bit like you're pimping us out." Serena remarks derivatively. "What are you going to do when they get here? Here's my daughter and her best friend, have your pick! "
Blair laughs at that. "That makes us sound like cattle at the auction. No, thank you. You can have him Serena!"
"You can have the friend then, Blair. I heard he's quite handsome. The career may be a bit less favorable though…" Lily pauses, "He's a writer." She says it like the career is akin to being a drug dealer. "But he did go to Dartmouth with Nathaniel so he must have some merit."
"Well, it doesn't matter to me anyways because I'm not interested. But thank you, Lily, I appreciate you thinking of me." Blair smiles kindly at her friend's mother to convey her gratefulness.
She was thankful after all for the kindness always shown to her by Lily. Given the girls had been best friends since childhood, each other's mothers were close friends and godparents to the girls.
But this summer, Blair wasn't in the mood to be set up. Last summer's romance ended in disaster and she had her fair share of blind dates that all went horribly astray since then. At 29 years old, she was happily single, having just completed her master's in communication.
Serena, on the otherhand, was eager to get married and have kids. She didn't quite have the commitment to a career like Blair. She had always floated from job to job, never sticking around long enough to climb the ladder. Her flippancy had always both irritated and endeared Blair.
"Anyways girls, I will see you both tomorrow!" Lily gives a regal wave. "Oh and Serena, wear your hair down and maybe that blue dress that brings out your eyes."
Serena sighs in exasperation. "Okay mom, bye!" Then she turns to Blair, "So what do you think?"
"About the blue dress?" Blair quirks a brow. "I think it's a bit predictable. Honestly, we should go shopping." She's already mentally making a list of the new wardrobe items she needs for the growing social calendar.
"About the guys," Serena corrects. "Not the dress."
"Oh." Blair twirls her straw, taking on a sardonic tone. "I hope one of them is your soulmate, S."
"You're such a spoilsport, B." Serena playfully nudges her. "Don't blame me when you're a lonely old spinster."
"And don't blame me when you've been thrice divorced from following your mother's dating advice," Blair lets her sunglasses slide down from the top of her head to her nose.
The next afternoon, after diligently doing their hair and makeup, Blair and Serena were finally ready to get changed and head to the van der Woodsen's estate. Blair had decided on a pale pink floral RED Valentino mini dress with an embroidered peter pan collar that she planned on wearing with red lace-up heeled Aquazzura sandals. In contrast, Serena had chosen a breezy, off-the-shoulder maxi dress with a thigh-high slit that showed off tan legs, clad in her calf-high lace-up flat sandals.
As with every year, the two arrived at the party a bit early to help greet guests. Especially since many of the guests were family friends. Blair's feet were already aching from trotting across the expansive mansion in stilettos, carrying floral arrangements and what not. By 5:30 pm, guests have already started trickling in but much to Lily's dismay, there had been no sign of the Archibald's.
"They said they would come. I just hope they don't show up too late." Lily says to Eleanor as she stood in the foyer of the mansion. Both women looked elegant as always, dressed in Waldorf Designs.
"Lily, dear, the party only started 30 minutes ago, I'm sure they will be here soon." Eleanor rationalizes. "The girls must be just as eager as you."
"I can assure you I'm not. Serena on the other hand…" Blair gestures to Serena who is eyeing the door.
"What?" Serena says distractedly upon hearing her name.
"See," Blair smirks at her best friend's predictability. "At least they'll have quite the welcome reception. I'm going to get a drink."
On her way back from getting a gin and tonic, Blair is stopped by the Coates family and makes small talk for a few minutes. Their daughter Isabel apparently just got engaged, yet another reminder of her ticking time clock, according to Hamptons society. When she finally returns to her mother, Lily, and Serena, she can see they're in the middle of a conversation with newcomers.
"Oh, there she is, Blair! Come meet our guests." Lily enthusiastically waves Blair over to where she stands. Blair can already tell from the way her stately face is uncharacteristically lit up, that the Archibalds must have arrived.
Before the women are a WASP-y woman of a similar age to her mother, and two guys in their late twenties. The one on the left, has high cheekbones, curly hair, and sports a dissatisfied expression. The other, Blair recognizes from the pages of society articles as Nathaniel Archibald, more commonly known as Nate. He's even better looking in person with his tan skin, Blair has to admit, with his golden-streaked brown hair, and blue eyes. Serena must be in heaven . Blair glances over at her and sees indeed, she's practically drooling.
"Blair, meet Anne Archibald," Lily gestures towards the woman and Blair shakes her hand. "Her son, Nathaniel Archibald," Blair outstretches her hand to meet Nate's and is met with a warm smile, "And his friend, Daniel Humphrey."
There's a brief pause in which Daniel Humphrey does not offer his hand to shake, as is socially expected. But then he seemingly reluctantly offers it and says, "Pleased to meet you," while looking completely unpleased.
How rude , Blair thinks. She wasn't interested before but now she's definitely not. Serena can have both of them for all Blair cares. She tries to mouth, What the fuck , to Serena but she's too busy swooning over Nate.
"Nate was just telling us about his career. It's quite fascinating." Lily continues and Blair starts to wonder if maybe Lily is after Nate for herself. She has touched his arm at least three times in this thirty-second interaction.
"Really it's not. Besides, I would hate to bore you with talks of politics at a party kicking off summer of all things." Nate says and the group chuckles along easily, except for his morose friend of course.
Once new guests start arriving, the girls are excused and the Archibald's and Daniel Humphrey recede further into the mansion. As soon as they're out of sight, Serena eagerly pulls Blair into the bathroom, her grip vice-like on Blair's arm.
"Oh my god, he's so hot, B." Serena says breathily. "I know it's totally lame to like someone my mother practically chose from me but you think so too, right?"
"Please tell me you're talking about Nate and not his insufferable friend." Blair remarks flatly. She looks in the mirror, checking her lipstick and finds no visible flaws.
"Of course! What's wrong with Dan, though?" Serena seems disappointed. "I thought he was cute too."
"Only the fact that he's incredibly rude and couldn't even bother to iron his shirt before coming to the party. Oh or at the very least use hair product to tame those unruly curls." Blair wrinkles her nose in distaste. "And let's not forget the fact that he almost didn't shake my hand."
Serena laughs, "No wonder you're still single, you have way too high of standards. Anyways, about Nate… What do you think?"
"He's hot, you're hot. You should go for it." Blair can't help her bored tone. She balances on the counter, relacing her red heels
"I'm so glad you think so too! Okay, let's go find him" Serena pulls Blair out of the bathroom and they rejoin the party. Once they're in the backyard, Serena heads over to where Daniel Humphrey and Nate Archibald are standing and strikes up a conversation. Before she joins, Blair announces she's going to the bar and strides across the lawn to get another drink. She's going to need it if she has to suffer the company of Daniel Humphrey once more.
"There you are, I've been looking for you." An all too familiar male voice says behind Blair and with it comes the smell of patchouli. She knows that scent, has washed it from the linens too many times…
"Aaron." She levels him with her most withering glare. "What are you doing here? Shouldn't you be at Burning Man or something?"
"I thought I would finally come see what the Hamptons are all about. Since you and Serena are always speaking so highly of this place. Besides, it means I get to spend all summer with you." Aaron says with a teasing smile.
Aaron Rose, Blair's stepbrother, is the bane of Blair's existence. He deludedly thinks there's something between them since Blair one time a couple years ago drunkenly flirted with him, prior to him becoming her stepbrother, of course.
The regrettable incident occurred at a party thrown by her mother and Blair had just gotten out of a relationship. She had way too much to drink that evening and was looking for something to distract her from her aching heart. Upon spotting Aaron, clad in a leather jacket which she later would learn was faux because wearing dead animal skin is akin to murder (in Aaron's words), her eyes lit up. On a rebellious kick, she thought, he looks just like what I need .
So she strode right up to him and said something flirty, batted her eyes at him, and bantered until she horrifically found out he was the son of Cyrus Rose, her mother's new boyfriend. As soon as she learned this information, clarity hit her and she was fully repulsed. Unfortunately, Aaron did not have the same reaction, with his newfangled ideas on free love, and the interaction seemed to spark some sort of long-enduring crush he wouldn't let go of.
"Torturing me three seasons out of the year isn't enough and you decided to hop on the jitney to make summer hell for me too? How very brotherly of you." Blair is full of sarcastic, irritated tones. She starts walking away but he trails behind.
"Blair, come on. How are you? I haven't seen you in months." Aaron sounds genuinely concerned for her well-being.
"I was quite well but then I saw you so now…" She looks off in irritation. "Not so great to say the least." Nearing Serena, Blair says, "Excuse me. Hope you enjoy the party, Aaron." She discreetly shoves him off in the other direction.
"Blair, guess what?" Serena exclaims. "Dan's our neighbor! Well practically at least, he's only a block down from us!"
So in the time Blair has secured a drink and dressed down her stepbrother, Serena has gotten on a nickname basis with him. Fan-fucking-tastic. Blair fights the urge to announce they'll be moving to another block. Or rather, another island.
"How very coincidental." Blair manages, blandly.
Not noticing Blair's clear irritation, Serena quickly fills her in on what they've been discussing and of course, it's basically just all about Nate. While Blair joins in on the conversation, she can't help but notice how very little Daniel, Dan , Humphrey, or whatever he wants to be called says. He's barely said three words by the end of the conversation.
But either way, Blair has learned enough about him to know he's a pretentious jerk. He went to Dartmouth with Nate and won some literary prize while at school. Now he's a writer for New York Magazine and lives in Williamsburg. Except for this summer of course since he's living in a cottage a block away. Granted, none of those facts alone make him sound that bad but it's all in his demeanor, Blair thinks.
After the sun has set and Blair has done her fair share of mingling, she heads into the kitchen to get a reprieve from the conversation. The windows are open as is the back door and she can hear voices near the door. She recognizes one of the voices as Nate's.
"I have to say, this party was a good idea. I know you had your doubts but I'm feeling optimistic about summer in the Hamptons." Nate is saying as Blair nears the door to listen a little better. She pretends to stir her drink in case someone is watching her eavesdrop.
"Spoken like a man who spent his night talking to the only woman worth talking to. The women here, Serena excepted, of course, are distasteful." Dan's dry voice says in response and Blair's mouth falls open.
"They're not all bad." Nate counters good-naturedly. "What about Blair? I hear she's single too."
"That doesn't surprise me," Comes Dan's harsh reply.
Nate gives a short laugh, "What's so bad about her?"
"She seems like the type of girl who only has a hearty appetite for shopping and gossip. Besides, how else would she maintain a 95-pound Jimmy Choo-wearing physique?" Dan's tone makes Blair want to step out of the kitchen and punch him squarely in his annoyingly-chiseled jaw.
"Well, there's bound to be someone here for you this summer." Blair listens in indignation as Nate doesn't even bother to defend her character. Certainly, he does not know her well but if he were so sincere about Serena, he should be quick to defend those who are important to her.
"Doubtful. In my short time here, I've learned there are two types of women in the Hamptons. Botoxed women with midlife crises busying themselves with throwing parties while their husbands screw their mistresses and label-whoring socialites scheming their way to the top of the social ladder. Of course, those categories don't include Serena."
"Wow, man, sounds like you've made up your mind about the Hamptons." Nate sounds a little resigned. "Are you going to use that in your article?"
"Perhaps."
Blair is frozen to the spot, fuming with rage. How dare that asshole speak about her and all of the other women in the Hamptons for that matter like that? The audacity…
Taking a deep breath, Blair strides out the back door and comes face to face with them. "Hello." Blair says as calmly as possible.
She doesn't wait for a reply as she turns to look Dan directly in the eye. "This label-whore, as you so eloquently put it, is actually wearing Aquazzura, not Jimmy Choo." Blair bites back the urge to tack on a fuck you and instead walks away cooly without a second glance.