Disclaimer: Neither these characters nor these scenarios belong to me.
The first time Blair dreams about Dan is on Valentine's Day. He's wearing a tuxedo, wandering around an indoor tennis court, calling her name. She watches him from the chair umpire seat, nervous, confused, and annoyed.
"Humphrey? What are you doing here? Where's Chuck?"
"I'm sure he's around here somewhere," he says nonchalantly, bends down to pour champagne into two glasses.
"You need to leave!" Blair points at the door. He only rolls his eyes and starts to stand back up, holding out a glass to her. She finally climbs down the ladder, explaining as she goes, "Chuck is going to be here any minute now, Humphrey, and you're not. I don't even know how you got in here in the first place, but you're just going to have to go."
Blair turns to face him and finds him standing very close to her. She comes up short, looks at his lips, gulps back the last of her speech.
"Blair, come on, you know Chuck isn't coming. It's just us."
Blair opens her mouth to respond, stops, just pouts instead. Dan smirks at her, pleased, dangles the glass before her. She grabs it and turns away to sip at her drink.
"I hope you don't object to me?" Dan mocks, a smile in his voice.
Blair presses her lips together, tries not to grin. She turns back and says, rehearsed and sarcastic, "Object? To you? It's as though a window had been thrown open and a lovely breeze swept through this stuffy old house. How could I object?"
"Even if the breeze comes from the general direction of Brooklyn?" He answers in his most affected accent. They smile at each other and he takes a sip of his drink. Blair peers at him over the rim of her own glass, looks at his lips again, averts her eyes.
"You could've at least done something with your hair," she says after a moment.
Dan rolls his eyes. "It's your dream."
A tune wafts in through the open windows. Blair's smile is wistful as she listens to the orchestra play "Isn't it Romantic". She eyes Dan, glass at her lips, waits for him to lead.
"There it is," she says. Her voice is practiced, expectant. Dan nods, looks suddenly uncomfortable, doesn't move forward.
Blair taps her foot on the ground, finally spits out, "Humphrey, aren't you going to ask me to dance?"
Dan stares at her, stunned. "Do you—do you want me to?"
Blair rolls her eyes. "It's my dream, isn't it?"
Dan walks over, puts his free hand on her waist, hers goes to his shoulder. She sighs, content, and shuts her eyes.
"I mean, you remember how this scene ends, right?" He mumbles into her bare shoulder, his breath warm on her skin.
"Mmm," she replies, hazy, "I don't see the harm, Humphrey." She can feel his smile against her as she loops a curl around her finger.
The second time Blair dreams about Dan is a week later. They're standing outside a dollar store and she's whispering into his ear, "Did you ever steal anything from a five and ten store? I mean, as a kid."
"No," he says, "Have you?"
He narrows his eyes. "Have you ever even been in a dollar store?"
"Humphrey, you have to play along! This is my dream!"
Dan leans down to her, grinning. "Well, have you?"
Blair throws her hands up, stomps off, turns and waves him over.
"When I'm in your dreams, I'm sure I behave myself."
"Oh, I highly doubt that, Blair."
She exhales sharply through her nose and eyes him. "My point is, Humphrey, this is my dream. So, just try to keep to the script."
Dan's mouth angles up in half a smile. Blair almost smiles back, grabs his hand instead and pulls him forward.
She looks around the store, shrugs off her discomfort, and starts to walk around as casually as she can manage. Dan walks by her side, his trench coat folded over one arm, his other hand in hers. It distracts her a little: their hand-holding. She doesn't want to let go, doesn't want him to know how much she likes it either. She tries to pick out one thing and then another, but the salesman is always eyeballing them, everyone seems to be. Blair shoots them a fake smile, moves to the next aisle. Dan watches her, his eyes twinkling in amusement.
"Come on, Blair, you're so nervous you're forgetting your own lines."
"I'm not nervous! And there is no dialogue in this part of the scene!"
"Weren't you supposed to try to smuggle out a gold fish under your enormous hat?" He says, motioning to the rack of fish bowls behind them. Blair looks down at the hat in her hands, remembers it for the first time. Dan pushes a strand of hair behind her ear and she lurches back without thinking.
"Humphrey, you've ruined everything! Now everyone knows that we're trying to steal something!" she whisper-yells through her teeth, one arm sweeping grandly toward their audience.
"Well, if they didn't before, they certainly do now," he responds, looking around.
Blair huffs, throws up her arms, takes a deep breath, and then says, "Just follow my lead, Humphrey!"
While the whole crowd is watching them, closing in on them, Blair picks out a mask carefully, Dan does the same. They put them on. Blair turns towards the crowd and curtsies. Bemused, Dan takes a bow by her side. Then, she knocks over a stand and makes a run for it. Dan follows, his hand still in hers.
She's laughing, happy, when they bounce into a cop crossing the street. Blair boos, Dan roars, and they're off once more, giggling all the way down Fifth Avenue. Blair pulls him, tells him to hurry, wants to get home before she wakes.
They stare at each other, breathing hard, masks pulled up. Blair bites her lip, waits.
"Are we sticking to the script?" Dan asks. His eyes move down to her bitten lip.
Blair shrugs, says "I suppose", and wraps her arms around his neck. She wakes up content, the ghost of his kiss still on her lips.
The third time, Blair runs into Dan in Rome. She strolls right up to him, at ease, used to him; happy to see him, even offers him some of her gelato. He's stunned to see her, his jaw tense, his eyes angry.
"Blair, what are you doing here?"
"Dan, how many times do I have to explain this? It's my dream; I do and go where I want. Rome was mine long before it was yours." She finishes her gelato, dabs at the corners of her mouth with a napkin, tosses away her trash.
"And you want to spend your dream following me around Rome?"
Blair rolls her eyes. "I didn't say that, either. Now, come on, put a smile on that face and let's go find that Vespa. I've got a city to see!"
Blair reaches out a hand to him, smiles and waits for him to take it. Dan just stares at her, upset.
"Where's Chuck, Blair? Shouldn't you be dreaming about him? He is the love of your life, right?"
Blair opens her mouth, surprised, but doesn't seem to know how to answer. "I—Dan—that's none of your business—it's not my fault you don't have anything better to do than hang out in my dreams all the time."
Dan rolls his eyes, suddenly thinks of something. He finally grabs her hand, pulls her down the street.
"Where are we going?" She shouts, but he just pulls harder, pulls until they're there: at the Mouth of Truth.
He lets go of her then, starts to explain, "The Mouth of Truth. The legend is that if you-"
"I know the legend, Humphrey!"
"What happened to sticking to the script?"
"Shut up," Blair says and folds her arms across her chest, "So, what? You want me to put my hand in there? What exactly is it that I'm supposed to be lying about?"
"Why are you dreaming about me, Blair?"
Blair scoffs at him. "You're my friend. I didn't realize I wasn't allowed to dream about you."
Dan leans towards her, whispers close to her ear, "Blair, if I was just your friend, I wouldn't be the guy you kiss at the end of the movie, I'd be the guy with the lighter that's actually a camera." He motions over to the man to their left pretending to light a cigarette.
Blair opens her mouth, shuts it, opens it again. "His name's Irving."
Dan smiles a little, bites his lip. "If you're not afraid, then do it, prove me wrong."
Blair looks at the Mouth of Truth, looks back at him. "If I do this, we drop the subject and go to the party on the boat? Start a fight? Jump into the river?"
Dan nods. "If you do this, I'll even let you smash a guitar over my head if you like."
Blair smiles quickly, briefly, licks her lips and takes a step forward, puts out her hand, feels along the stone. Just before she places her hand inside, she pulls it back, smiles at him mischievously. "Let's see you do it, Dan."
"Blair-"
"No, Dan, it's my dream and I'll make the rules. I'll do it as soon as you've done it first."
Dan stares at her, shaking his head, puts his hands on his hips. Blair watches him, smiling.
"What? Are you afraid? What've you been lying about, hmm?" Blair whispers into his ear.
"Fine, I'll do it. This thing doesn't work anyway."
"Don't spoil the ending, Humphrey."
"Let's get this over with." Dan walks over, puts his hand in slowly at first, hesitantly, then he's smiling, triumphant, and moving his arm further and further in. Blair rolls her eyes, waiting for it, fighting a smile.
"See, Blair, you're the only liar here."
Blair rolls her eyes. They smile at each other for a moment, both of them happy.
Blair wakes up when he's screaming, his hand still caught in the stone, and even though she knows how it ends, she feels unsettled, uncomfortable, wishes she could've seen it to completion, wishes she knew if they were okay, if they were liars. Try as she might, she can't get back to the dream and she's left with a feeling, deep in the pit of her stomach, that tastes like regret.