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Serena had always loved the little café in Brooklyn Dan had used to bring her to. Even after her and Dan broke up, and Vanessa stopped working there, depriving Serena of any valid excuses to go all the way to the outer boroughs for a cup of coffee, she still would come by every once in a blue moon, just for old time’s sake.
She had never run into Dan there on one of her little visits, but it was bound to happen sometime, so she’s not surprised when she walks in on a Saturday morning to see him sitting at a table. What is surprising though is that he’s not alone: sitting across from him is Blair. Even weirder is that the two of them are laughing, seemingly getting along perfectly.
“Dan, Blair?” Serena calls out as she walks over to their table, more than a little confused. “What are you two doing here together…and what are you laughing about?”
“Epperly’s breakfast order,” they both say at the same time, still laughing. Clearly that was some inside joke Serena wasn’t privy too.
“I didn’t realize you two were so…” Serena hesitates, struggling to find the right word. “Friendly,” she finishes.
Blair shakes her head. “Oh, we’re not friendly.”
“No, no, Blair came over here to try to blackmail me into quitting my job at W,” Dan says. But he’s still smiling.
“Yeah, that’s because Humphrey got in off of nepotism, while I actually want to be there,” Blair tells her. “Croissant,” she asks Serena, under-pronouncing the T the French way.
“Croissant,” Dan corrects, pronouncing it the American way. And then, as if Serena wasn’t there, they go right back to laughing about inside jokes from W again.
Serena is confused for a few more seconds before it hits her: Dan and Blair are flirting. And she’s not even sure they realize it.
On the one hand, the idea of her best friend and her ex-boyfriend together is a little strange. But on the other, it’s been years now since her and Dan were together, and she had always tried to get Dan and Blair to see how much they actually had in common. The more Serena thinks about it, the more she realizes they make perfect sense.
But how is she ever going to get them to see that?
---
At lunch with Eric that afternoon, he tells her about his college interview, and how due to some unfortunate circumstances involving Gossip Girl, he had to move it and came up with the crazy idea to do it at the Central Park Carousel of all places, but to his surprise it had actually worked, and the interview had gone well.
“Well, sometimes the craziest ideas are the most brilliant ones,” Serena responds, unable to hide the smirk on her face.
Eric’s expression falters, always able to read her well. “Oh no…what does that mean?”
“Nothing bad, don’t worry,” she assures him. “I’ve just decided that I’m going to bring two unexpected people together and provide them with a lifetime of happiness.”
“And who exactly is the target of your arrow here, Cupid?”
“Dan and Blair.”
Eric chokes on his water. “Are you joking?”
“The heart wants what it wants, Eric. Now, if you’ll excuse me, I have to make a quick phone call.” Serena gets up from the table, ignoring Eric’s stare of disbelief.
---
Before bed, she places quick calls to Dan and Blair, telling them each that she has the perfect solution to their W dilemma and to meet her at the Van der Humphrey penthouse the next morning for breakfast. They’re both annoyed that she won’t just tell them over the phone, but Serena is more than capable of getting her own way, and eventually wears them down into agreeing to meet.
Once they’re all together again, she sits them down, telling them, “Good news! I got Dan an internship at The New Yorker. So now you two won’t have to compete against each other anymore.”
Dan and Blair look at each other uncertainly. “Um...that’s great, thank you…” Dan responds.
“But how on Earth did you pull that off?” Blair asks.
Serena shrugs. “I got William van der Bilt’s number from Nate’s phone and told him that I would go public with my affair with Tripp if he didn’t call in a favor for Dan.”
“Serena!” Dan exclaims, shocked.
“Oh, don’t worry,” she waves him off. “I wouldn’t have done it, I just needed him to believe I would.”
“Wow…I’m kinda impressed, S. I’ve taught you well,” Blair tells her.
Serena smiles to herself but tries to keep a straight face as she says, “Well, don’t praise me yet. There is one little thing…”
Dan and Blair look over at each other again, with raised eyebrows. “Uh huh,” Dan says skeptically.
“It seems that William is planning on investing in some fancy new restaurant. But before he does, he wants to have someone the owners don’t know check it out, see what it’s really like. And as part of our deal, it has to be the three of us.”
Blair sighs. “Fine, whatever.”
Dan shrugs. “Yeah, I could have a free meal on William van der Bilt, sure.”
“You made it seem like a big deal, though, S.”
“Oh, well, I just wasn’t sure you guys would agree. But great! I’ll see you there tonight!” She smiles at them, before adding, “Oh and dress real nice. It’s apparently a romantic place.”
She can’t help but laugh internally at Dan and Blair’s uncomfortable faces.
---
That night at dinner, Serena is pleased to see that Dan and Blair have both dressed their best, and she does not miss the way Dan’s eyes bug out of his head when Blair first walks in, or the glances Blair keeps shooting at Dan anytime she thinks he isn’t looking. This is going to be even easier than she thought.
Halfway through the second entrée, Serena gets started with her plan. “You know…you two really have both grown and changed so much over the years.”
Blair and Dan share another look, before they both look over at her strangely, Dan asking her, “Okay, what is going on with you?”
They look over at her skeptically and Serena wishes in that moment that she possessed Blair’s natural talent for scheming and manipulation. But she does have one thing, her charm, bursting out into fake laughter instead.
“What’s so funny?” Blair asks, clearly suspicious.
“Oh, we’ve just known each for a long time now. Do you remember that awful photoshoot of your mom’s that I invited Dan to?”
“I knew it, I knew it!” Dan cries.
“Knew what?” Serena tries to play dumb.
“This is exactly like the photoshoot, you have always tried to get Blair and I to be closer, so we can be this tight little trio!”
Blair rolls her eyes. “Ugh, not again. When are you going to stop? We have nothing in common!”
“Hey, well, excuse me for wanting the two of you to see in each other what I do.”
But it’s almost as if she’s not there again, Blair asking Dan, “Do you remember that time she brought you and Vanessa to my birthday party?”
Dan laughs. “I do, I do. Do you remember the time she made me help you with Chuck of all people? God, Serena, no offense, but you can be so annoying.”
“So fucking annoying,” Blair agrees.
But Serena takes no offense, just smiling to herself as Dan and Blair unknowingly flirt again. “Yes, yes, I can be.” She pretends to gasp then. “Oh my god, I totally forgot I promised my mom I’d pick up my necklace from her place tonight.”
“Oh, we can just head out – “ Dan starts to say, but Serena quickly cuts him off.
“No, no, you two stay, I’ll just be right back.” Serena stands up quickly, walking off to where they can’t see her, watching as they pay her no mind, already back to trading anecdotes.
---
Serena doesn’t bother coming back that night, going off to hang with Eric and his new boyfriend instead, before staying over at her mom’s. She doesn’t hear anything more from Dan or Blair, which she hopes is a good sign, but knows could also be a really, really bad one.
When she still doesn’t hear anything by eleven AM the next morning, she starts to get worried. She knows that neither of them are late sleepers, they definitely should both be up by now, and she should have about a half dozen texts wondering where she went last night. She’s starting to grow worried; maybe they figured out her plan and the whole night went so poorly that now her two best friends aren’t speaking to her. No, she can’t have that, she has to go and talk to both of them.
She decides to stop by the loft first, knowing Dan’s anger will be much more manageable than Blair’s. The front door is unlocked as always, so she walks right on in, only to stop in surprise as she takes in the sight in front of her. Dan making breakfast in pajamas with his hair mused isn’t actually an usual sight, but Blair sitting across from him in just Dan’s shirt from the night before certainly is.
“Oh,” is the only word Serena can find in herself to say. She had hoped it would go well, sure, but she never would’ve guessed her plan would go this well.
Dan and Blair seem to be equally shocked, staring back at her like two deer in the headlights. “S…wha - what are you doing here?”
“I just…I hadn’t heard from either of you since last night and I thought, um, I thought maybe you were mad at me or something, anyway, it doesn’t matter, I’m clearly interrupting, I’ll just – “
“Why would we be mad at you for ditching?” Dan asks. “No offense Serena but leaving suddenly is kinda your signature.”
Serena shakes her head quickly. “No, no reason, I’m just gonna – “ She turns back to the door, trying to speed walk out of there, but then –
“Wait!” Serena sighs, turning back towards Blair, knowing instinctively she’s been caught. “You seem surprised to see me here, but not upset. You thought we’d both be mad at you for leaving early. You were the one who made the dinner plans in the first place,” Blair analyzes in her usual calculating manner. “You tried to set us up!”
“Tried? Clearly it worked,” Serena snarks back.
“Serena!” Dan exclaims.
“Hey, I thought I saw a spark between you two and obviously, I was right, so really you both should be thanking me. I’ll take payment in naming your first born after me,” she teases, giggling at the blush that overtakes both of their faces.
“Alright, you’re done,” Dan groans, spinning Serena around by her shoulders, leading her back towards the front door.
“How about just maid of honor duties?” Serena calls back over her shoulder as they reach the threshold, Dan lightly pushing her over it. “Oh, B, I’m gonna throw you the best bachelorette party!” she adds, as Dan shuts the door in her face. “Dan, when it comes time to pick out the ring, you better bring me, Blair made me memorize her dream cut when I was ten,” she yells through the closed door.
A thump sounds against the door then, sounding suspiciously like a thrown newspaper. “Serena, go away!” they both shout at the same time.
“Already in sync,” she smirks to herself, before leaving for real this time, and heads back to her mom’s to find Eric.
She has some gloating to do.