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Blair isn’t sure why she agreed to go on a road trip with her ex-boyfriend, her best friend, her best friend’s ex, and his best friend. Maybe Serena drugged her or put a spell on her with her shiny hair or something, because this is definitely the dumbest thing Blair has ever agreed to do for her. And she’s agreed to a lot of dumb things for Serena.
“It’ll be fun, B,” Serena had begged. “Dan has to go visit his grandmother down in Florida, and Jenny can't go, so Vanessa came up with this idea to drive down instead and hit all the beaches, and then Nate heard about it and invited himself along, and now I’m going too, and I really think you should come with. What else are you going to do with your summer?”
“Read Jane Austen. Visit the new Degas exhibit at the Met. Do some practice tests for the GRE, it’s only two years away, you know,” Blair replied, trying to stay firm.
“You can do all of that stuff when you get back, we’ll only be gone a few weeks. Come on, don’t waste your youth!” Serena giggled.
Blair knows she must’ve agreed at some point, but it’s all a blur, because the next thing she knows she’s in Brooklyn, putting luggage in the trunk of the Range Rover Nate borrowed from his grandfather, and climbing into the backseat next to Serena and Vanessa. In the middle seat, no less. How on Earth did this become her life?
Humphrey is sitting shotgun, which means he gets control of the aux cord. Blair is worried at first, not looking forward to hours on end of pretentious Indie crap, but she’s pleasantly surprised when he puts on some Radiohead instead.
Serena and Vanessa are less enthused. “Dan, this is terrible road trip music,” Vanessa complains.
“Yeah, I’m not listening to this. Here.” Serena leans forward and invades Blair’s personal space, unplugging Humphrey’s phone and plugging in her own. Soon, they’re driving across the Verrazano-Narrows Bridge, Serena and Vanessa scream-singing to “Teenage Dream” while Blair is stuck in between them.
She surprisingly doesn’t hate it.
---
They’re barely on the road an hour before Nate complains that he’s hungry, ignoring Blair’s protests as he pulls into the parking lot of some hole in the wall diner on Staten Island. Blair shudders as she walks in, positive she’s going to get hepatitis or something here.
Blair, Humphrey, and Vanessa grab a booth while Nate and Serena head to the counter with plans to grab drinks for them all. “Will you look at them?” Vanessa says. Blair glances over to see them heavily flirting, Serena batting her eyelashes and flipping her hair. “How long until they hook up?” Vanessa continues.
Blair shoots Vanessa a glare, a little stab of jealousy hitting her. It’s been years since high school, but there’s still a part of her that thinks of Nate as hers and she’s not sure that will ever go away.
“Those are our exes you’re talking about, you know,” Humphrey says wryly, gesturing to himself and Blair. She doesn’t appreciate being lumped together with him.
Vanessa throws her hands up in surrender and mercifully changes the subject.
She’s right though. At the Bed & Breakfast they all stay in at Cape May that night, Blair’s room is next to Serena’s and she gets stuck having to listen to her and Nate go at it all night long.
Blair’s absolutely exhausted by the time the sun comes up the next morning, and to add insult to injury she’s forced to go to Wawa of all places to get a decent cup of coffee. When she gets there, Humphrey’s standing outside with his own cup, smoking a cigarette. “You smoke?” she asks, shocked. She definitely doesn’t remember him ever doing that in high school.
Humphrey shrugs. “Only when my ex keeps me up all night fucking my friend.”
“You heard that too?”
“I think people in the next B&B over probably heard them. Hey, wanna go get breakfast?” he asks, flicking his cigarette butt away. Blair starts at the abrupt change in subject, but agrees, not wanting to have to eat breakfast by herself, since it seems Serena, Nate, and Vanessa are all going to sleep in until well past noon.
Breakfast with Humphrey isn’t half bad. It’s the first time she’s ever spent more than 5 minutes alone with him and she’s surprised to find that he’s actually a pretty decent conversationalist. By the time they get back the rest of the group is up, and they all head out to the beach for some sun.
While Serena and Nate frolic like children in the water, Vanessa pops in some headphones and promptly falls back asleep, so Blair pulls out her well-worn copy of Pride & Prejudice. She glances over at Humphrey, expecting him to be scribbling something in a notebook, but instead he’s glaring after Serena and Nate. “Jealous much?”
Humphrey ignores her, getting up and going to join them in the ocean. Blair pretends she doesn’t care.
---
They make it all the way to Maryland before Nate hooks up with Vanessa.
Serena had made them take a long detour to Assateague Island so she could see the wild ponies and by the time they were able to get back across the bay, it was too late to go anywhere but a shitty motel, with an even shittier bar across the street.
It’s the kind of place that only serves beer and cheap liquor, and Blair purells a bar stool before she will even sit down. They play a quick game of pool, Serena creaming them all.
Humphrey looks on, incredulous. “You hustled me!”
Blair, Nate, and Vanessa are all lost, but Serena seems to know what he’s referring to, looking smug.
“Were you trying to make me feel better about that horrible French restaurant or did you just want an excuse for me to put my arms around you?” Humphrey continues.
“A girl never reveals her secrets.”
Blair rolls her eyes, and walks back to the bar, but to her dismay, Serena and Humphrey come along after her. Nate and Vanessa hang back, heading over to the ancient jukebox in the corner.
Serena makes the three of them do shots and it isn’t long before they’re all piss drunk. So, when Blair looks over to the corner and sees Nate and Vanessa making out, she’s initially not even sure if it’s real or if she’s just imagining it. However, when she glances back at Serena and Humphrey, they both seem to have sobered up quick, sending death stares towards Nate and Vanessa. Blair’s mostly annoyed; she didn’t sign up to spend her summer amongst the world’s most convoluted love square.
The next morning, Vanessa is wearing one of Nate’s shirts and Blair swears she sees Serena’s eyes turn red with rage. Blair really doesn’t want to talk about Nate and Vanessa’s conjugal activities, but she knows Serena would do it for her, so she corners Serena in a gross gas station bathroom and asks if she’s okay about everything with Nate.
“I don’t give a shit who Nate Archibald fucks,” Serena bites back, leaving Blair mostly just confused, but she drops it. Humphrey is in a weird mood as well and Blair curses her short height as she’s squeezed into the middle seat again between the two moody exes, while Nate and Vanessa flirt nauseatingly in the front.
---
Nate and Vanessa’s tryst seems to be over by the time they make it to Virginia Beach. The beachfront is packed with people and they’re only able to get two rooms. They split into guys and girls, Blair assuming she’ll have to share a double bed with Serena while Vanessa sleeps solo. But when they get to the room, Serena tells Blair she kicks in her sleep and puts her stuff onto Vanessa’s bed instead. Blair expects Vanessa to make a fuss, but she simply shrugs and smiles. Blair assumes it’s some weird power struggle over Nate and forgets about it quickly.
Blair makes them go out to a five-star restaurant for dinner that night. Vanessa and Serena cram in next to each other on one side of the booth, Nate taking the lone chair, forcing Blair to squeeze into the booth next to Humphrey. It’s a tight fit, the two of them pressed together, their knees brushing up against each other every few minutes. It’s not as uncomfortable as she would’ve thought.
The next morning when she wakes up, Vanessa and Serena’s bed is empty. It’s unmade though, so she figures they went down to the beach or something. She heads over to the boys’ room instead, finding it unlocked. She barges in, a lecture about safety on the tip of the tongue, when she realizes that the double bed closest to the door is still made. She looks over to the other bed and there’s Nate and Humphrey, curled up against each other, clearly naked.
She backs out of the room slowly, a gauntlet of emotions running through her. It’s one thing to see her ex-boyfriend with other women, but another guy? And a Brooklyn-bred one to boot? Blair is insanely bothered by this turn of events and is not sure why, considering her and Nate are long over. She didn’t feel this jealous about Serena or Vanessa, so she just chalks up her anger to Nate turning her into a cliché, a girl who can’t help but date men just like her father.
Blair goes to breakfast by herself, wanting to be alone with her thoughts, but as she’s finishing her third cup of coffee, Humphrey shows up and takes a seat across from her. “I saw you,” she finds herself blurting out before she can stop herself. “You and Nate, I mean,” she clarifies. “You really should lock your door at night, it’s not safe.”
“Ah. Okay.”
His nonchalance only infuriates Blair more. “Well, aren’t you going to say anything? Are you guys a couple now?”
Humphrey shrugs. “Not any more than Nate and Serena or Nate and Vanessa, no.”
“So what, that was just a one night stand of homosexual experimentation?”
“No, I mean…I’ve had a thing for Nate for a while now. But I don’t know if that could really work long term, you know? It’s Nate.” Blair hates that she knows exactly what he means. “It was fun and nice and a long time coming, but if it never happens again, it won’t be the end of the world. It was just nice to know my attraction wasn’t one sided, it wasn’t all in my head.” For some reason, she thinks of Serena in that moment, before immediately burying that thought way back down to whatever depths it just came from.
Blair is not one to have trouble with her words, but the only thing she is able to say in response is a simple “oh”.
Humphrey smirks. “Were you jealous? Nate can be a very hard person to get over, I know.”
If it wasn’t already embarrassing enough that Humphrey was trying to bond with her over their shared attraction to Nate, Blair feels heat rise to her cheeks and realizes she’s blushing. “No, of course not,” she lies. “I just figured the love square on this trip was messy enough as it is. As fun as it would be in the moment, I don’t really want to deal with the aftermath of Serena and Vanessa clawing your eyes out.”
“Eh, I don’t think you really need to worry about that,” Humphrey says cryptically, making Blair knit her eyebrows together in confusion. He just laughs gently, before asking if he can finish the rest of her lightly buttered toast. Blair doesn’t know why she gives it to him.
---
Nate finds a teenager wiling to deal him weed on the Outer Banks. Blair hasn’t tried pot since she was fifteen and impressing Nate was one of her main priorities, but the rest of the group is clearly experienced with it. Their Bed & Breakfast has a hot tub out back where they light up, everyone struggling not to drop the joint into the bubbling water. They play drinking games with cheap beer, and despite having already spent four years in high school, no moment in Blair’s life has ever felt more high school than this one.
“Okay…hm. Never have I ever done coke,” Nate says.
Serena is the only one to take a drink. “Fuck you, Archibald,” she laughs, playfully splashing him. “Um, never have I ever…no, wait I’ve done that. Uh…”
“Okay, someone else go, or we’ll be sitting here all night,” Vanessa interrupts. “Blair?”
Blair looks around in surprise. She hadn’t actually had to take a drink the whole game so far and she definitely did not think that Vanessa of all people would notice that. “Oh, um…never have I ever hooked up with someone of the same gender.” She says that for Humphrey and Nate’s benefit, but to her surprise Vanessa and Serena take sips as well.
Serena, incredibly drunk and a little high, begins to stroke Blair’s hair. “Look at Blair, our token straight.” Blair blushes as the rest of the group lightly tease her. “Okay, Dan, your turn,” Serena all but demands.
“Okay. Never have I ever…hm. Never have I ever gone skinny dipping.” The rest of the group, Blair included, take a sip at that one as well. Humphrey looks at her quizzically, maybe even a little intrigued, but she doesn’t really want to let her mind go there.
She simply shrugs back at him. “Nate and Serena got me to go in the Hamptons once,” she tells him.
“That’s kinda hot,” Humphrey blurts, immediately blushing. “Sorry, I didn’t mean –“
“No, it was kinda hot,” Blair smirks back at him. It must be the combination of the weed and cheap beer getting to her, because surely she wouldn’t be flirting with Humphrey if she was in her right mind.
“Blair, Dan, focus,” Nate calls out to them and Blair silently thanks him in her head for ruining the moment, unsure how far she would’ve taken it. She spends the rest of the night trying not to look directly at Humphrey, even though she can feel his eyes watching her. She doesn’t trust herself otherwise.
---
Blair has a moment of weakness in Charleston.
She had dragged the whole group along with her on a walking tour, desperate to see the historic architecture. Serena and Vanessa had split off early after encountering a trendy art gallery along the way, and Humphrey eventually split as well when they reached Hampton Park, claiming it was the perfect spot to get some writing done, leaving Blair alone with Nate.
She was worried at first that it might be a little awkward, what with their history and all, but perhaps the romance of the city was getting to her, because it feels just like old times. Nate is the perfect gentleman, helping her along shaky cobblestone steps, lending her an arm to hold onto, taking her out to dinner afterwards at a restaurant overlooking the water.
So when they walk back to the hotel and Blair gives him a peck on the lips, it’s only meant to be a friendly gesture, a thank you for staying with her all day. But it doesn’t stay that way, and soon Nate is trying to kiss her neck while opening the door to his room, pushing her back onto the bed, and pulling her dress over her head.
The sex is great, certainly better than it was in high school, but Blair knows better than to think this is actually going anywhere. It was just a shared attempt to return to a safe past that was long gone. She puts her dress back on in the dark and sneaks out while Nate sleeps.
However, her quick getaway is ruined when she runs into Humphrey in the hallway, evidently just getting back to his own room after his writing stint. She knows he knows what just happened in Nate’s room and he knows she knows he knows what just happened in there too.
“Don’t judge me. It was just sex. Besides, I like Nate better when he isn’t talking.”
Humphrey simply raises an eyebrow. “Hey, no judgment here. Believe me, I get it.” His tone is neutral, but something feels off about this whole encounter, like Humphrey’s upset or something. Blair wonders if he still has lingering feelings for Nate after their one-night stand.
“Okay, well, goodnight,” she says awkwardly, heading back to her own room.
She doesn’t turn around as he calls out and wishes her a goodnight back.
---
Everything feels different with Humphrey after that night in Charleston. He brings her coffee the next morning, actual good coffee from some quirky coffee shop he found, presenting it to her without a word other than “here”.
As they all head out to the car to drive down to Savannah, their next stop, Serena and Vanessa climb into the back. Blair figures Humphrey will call shotgun or make a claim that he gets to sit up front due to his longer legs, but instead he simply opens the passenger door for her and closes it after she gets in. It’s a level of gentlemanly politeness she wouldn’t expect from someone raised in a loft.
The drive goes by surprisingly quick and when they get to the hotel, Humphrey insists on carrying her bags in. She’s starting to become convinced this is all a trap, that he’s setting her up for some kind of revenge for sleeping with Nate, so she pulls him aside. “Humphrey, what on Earth is going on with you?”
He blinks back at her, eyebrows drawing together. “Wha– what do you mean?”
“What’s with the southern gentleman act?”
He sighs. “Oh. That. Nothing, I’m just trying to be nice.”
“So you’re not just tricking me into feeling comfortable before you finally enact revenge on me for sleeping with Nate?”
Humphrey shakes his head in frustration. “I’m not one of your minions, Blair. And I told you, I’m not – I’m not upset that you slept with Nate. I just thought that we were kinda becoming friends.”
Blair starts to feel a little bad. “Oh. I’m sorry. You’re right. I’ll deny this if anyone ever asks, but I maybe sorta consider you a friend too. But on a probational period only, Humphrey, so don’t get cocky.”
Humphrey raises his hands in mock surrender. “Fair enough. You know…my friends usually call me Dan.”
“Whatever you say, Humphrey.”
He does that frustrated little head shake of his again, but Blair can tell he’s trying to hide a smile.
---
At lunch, Vanessa rightfully points out that she hasn’t gotten to choose the day’s activity once yet and tells everyone she signed them all up for a ghost tour that night. There are some minor protests, Blair included, but then Vanessa shoots Serena a look. “Come on guys, I bet it’s fun,” Serena pleads, and Blair wonders when she became such a sap for Brooklynites.
While Blair isn’t too enthused about the night’s activity, she assumes it will just be a lot of boring walking in the dark. But apparently Vanessa had chosen the scary, haunted ghost tour, the one that leads directly to a cemetery. And yes, maybe a guy in costume had jumped out at them, causing Blair to scream and grab Dan’s hand. And maybe Blair didn’t let go until the tour was finally over. It’s only because she knew Dan would be nice enough not to give her a hard time about it, whereas Nate would’ve teased her and gotten the guy to scare her again. That’s all.
Dan walks her back to her door afterwards, telling her he’s just concerned about her safety. There’s no teasing in his voice at all and Blair surprises herself, hugging him goodnight. He looks at her strangely afterwards, and Blair gets self-conscious, wondering if there’s something on her face. But then he simply wishes her goodnight and that’s that.
Blair’s room is right next to Serena’s again and she’s rudely woken up to sex noises at two in the morning. Unsurprised that Nate and Serena have found their way back to each other already, Blair pulls on the hotel robe and heads next door, furiously pounding on the door. “Serena van der Woodsen, some of us actually do need beauty rest, you know!”
Serena finally sticks her head out the door, hair mussed, and wearing the same hotel bathrobe as Blair. “What do you want, B?” she asks, annoyed, which Blair finds real rich considering she’s the one being kept awake.
“Can you and Nate please turn down the volume of your nocturnal activities? I’m trying to sleep.”
Serena rolls her eyes but won’t look at Blair. “Fine, whatever.” Blair knows that’s the best she’s going to get from Serena tonight, and huffs, before heading back to her own room.
The next morning, she makes a comment to Nate about her rude awakening at his own hands, but he just looks at her, confused.
---
They had finally made it to Florida and were driving down the A1A when the Range Rover gets a flat tire, not too far from Daytona. Of course, Nate being Nate, he had never made sure there was a spare in the trunk, and the group is forced to sit on the side of the road and wait for Triple A to show up.
The water is less than a hundred feet away from them, so Serena and Vanessa head down to get some extra beach time. Blair is about to join them, but before she can get up, Dan asks her if she would like to go on a walk with him instead. Blair finds herself saying yes.
As they walk down the road, Nate calls out after them. “You’re really just going to leave me here with the car?”
Dan turns, walking backwards. “You’ll be fine, man!” He then gives Nate a look that Blair can’t decipher.
The walk with Dan goes well, until about a half hour in when Blair suggests they head back, feeling bad that they left Nate to deal with the car by himself.
Dan huffs. “Nate’s a grown man, he can take care of it.”
“Humphrey, he never even bothered to make sure the Range Rover had a spare. I really think we should head back.” Blair turns around and begins to walk back without waiting for an answer. She knows Dan will follow her.
And he does, but not without groaning dramatically first. Maybe the sun and humidity are getting to her, because Blair snaps at that moment, getting up in Dan’s face angrily. “Okay, what the fuck is your problem? We were having a nice time until I mentioned Nate. Now, you’re acting all weird and jealous.”
Dan can’t seem to look her in the eye, so she continues. “Look, sleeping with Nate meant nothing to me okay? It was just a one-night thing. He’s all yours, you can have him!”
She goes to walk away but he softly calls her name. Despite herself, she turns around. “Blair,” he says again. “You’re right. I am jealous. But not of you. Of Nate.”
Blair doesn’t know what to say, too many feelings and emotions surging within her at once, but it doesn’t matter, because Dan keeps going. “I didn’t even realize I had feelings for you until I saw you walking out of Nate’s room that night. I know it's pathetic, the guy who doesn’t know what he wants until he can’t have it, but there’s more to it than that. I saw this whole other side of you on the trip. You’re intelligent, and intuitive, and outspoken, and independent, and just…really beautiful. And I know you don’t feel the same way about me, but I just had to let that all out or I would’ve gone crazy –“
“Oh, Dan,” Blair cuts him off, before pulling him into a kiss. He kisses her back rather enthusiastically, to the point that a passing car honks at them. Blair thinks absently that she should probably be very embarrassed but finds she doesn’t care at all.
---
Eventually, Triple A does come and save them, and they finally make it to the hotel in Miami a little after midnight. Blair feels silly getting a separate room for herself, knowing that she’s just going to end up sneaking into Dan’s, but hey, what’s her mother’s credit card for if not ridiculously extravagant purchases?
Blair drops off her stuff in her room, changing out of the bathing suit she’s been stuck in all day, and puts on her nicest lingerie under the dress she was wearing. She dabs some perfume on her neck and inner thighs, touches up her make-up, and takes a shot of mini-bar Vodka to calm her nerves before heading over to Dan’s.
He opens the door in bare feet and what she assumes are his pajamas, boxers and an old Lincoln Hawk t-shirt. He smiles but looks a little confused. “Blair, hey, what are you doing here?”
“Surely you can figure that one out,” she replies, pushing her way into the room without waiting for an invitation. She raises an eyebrow at his ensemble. “You really put on your pajamas?”
Dan blushes. “I didn’t want to assume. We don’t have to have sex right away, if you want. I can wait.”
Blair wraps her arms around his neck. “Your little gentleman act is sweet, but I have two-thousand-dollar lingerie on under here that I’m not planning on letting go to waste.”
“Two thousand dollars? Are you joking?”
“Nope, so don’t rip it.” And with that, Blair finally does what she’s been wanting to do since they parted on that roadside and kisses him again. Any hesitation he had must’ve melted away, since he eagerly kisses her back and lays her gently down on the bed…
Blair wakes up the next morning sated and sore, in the best way. Dan’s still peacefully asleep next to her, curls in a disarray. She spots several love bites and hickeys on his chest and blushes, wondering what her own body must look like. It’s going to be tough to hide those at the beach.
She gets out of bed and puts her clothes back on, thinking she can fit in a quick shower in her own room before everyone gets up and wants to get breakfast. She leaves him a note, one that she rewrites five times trying to find the perfect tone, and quietly tiptoes out of his room.
Right as she is softly closing the door to his room, the door across the hall, Vanessa’s room, opens up. Only Vanessa isn’t the one who is leaving. It’s Serena, sporting a very similar “recently fucked” look like Blair. The two of them stare at each like deer caught in headlights, neither of them knowing what to say.
Finally, Serena says something. “You…and Dan?” Blair finds she can only nod in response. “Well, I guess that’s going to make it a lot easier when I tell him I’m fucking his best friend.”
“So, you and Vanessa…that’s actually a thing?” Serena shrugs and blushes. “Well, you certainly have a type, S.”
Serena just smirks. “Come on, B,” she says softly, holding out her arm. “Let’s go get something to eat and talk about our crushes.”
Blair intertwines her arm with Serena’s, feeling sixteen again in the best way possible.
---
After another day spent at the beach, the whole group gets an early dinner before Dan has to catch the Tri-Rail to Boca Raton and his grandmother’s. Everything’s out in the open, Dan with his arm wrapped around Blair, Serena and Vanessa holding hands, Nate thoroughly confused by the whole turn of events.
“So, wait you two are a thing now?“ he asks, looking over at Serena and Vanessa. They both nod affirmatively.
“Have been for a little bit now,” Vanessa snarks.
“Yeah, keep up Archibald,” Serena laughs.
“And you two are a thing too?” he asks Blair and Dan. They look at each awkwardly. They hadn’t exactly had time to have a “define the relationship” conversation between three rounds of sex.
“If she’ll have me,” Dan says, looking at her fondly.
Blair rolls her eyes. “Ugh, you’re such a sap.” But she can feel the smile growing across her face.
Dan glances down at his watch. “Damn, my train leaves in fifteen minutes. You guys probably have to get up early tomorrow anyway to start driving back.”
The rest of the group share a silent glance of agreement, before Nate speaks for everyone. “Actually, maybe the four of us will just hang around Miami a few extra days and then we could all fly back to New York together?”
“What about your grandfather’s car though? Doesn’t someone need to drive it back up?”
Nate shrugs bashfully. “He has people who can do that for him.”
“Ugh, rich people,” Vanessa groans.
Nate winks at Vanessa and gestures at Serena. “Hey, you know you secretly love us.”
“Wait. You three never…together -“ Dan asks.
“No, but now I really wished I had tried," Nate jokes.
Serena and Vanessa both start to throw fries at him. Blair laughs and leans back into Dan’s arm, as he plants a kiss on the top of her head.
She can’t remember the last time she was this happy.