Takes place after the events of the 4a finale
Will Scarlett shoves his hands into his jacket pockets, wraps his fingers around the flask and papers stuffed inside them, and pulls edges closer together against the cold. The town is finally beginning to thaw now that the the Snow Queen's gone, but it's still the end of winter in Maine and the wind nips his skin red as he walks down Main Street. Where the hell is she? He's been to the queen's home, her office, even poked around outside her vault, bloody creepy place that was, and found no trace of her.
What he needs now is someplace warm where he can sit and think. Granny's it is, then. The place is always open, no matter what kind of catastrophic event has taken place, and though he rarely frequents the establishment, there is something comforting knowing that there's always a place where you can go get a burger when the fancy strikes you. Or you have money. Which he doesn't, but he's yet to be kicked out for loitering somehow.
Ahead of him on the street, the sheriff and the pirate are walking around the back side of Granny's toward the boarding house entrance, and for a moment he considers going elsewhere to warm up. He shakes away the thought and presses on. If the "savior" should choose to confront him, he's got her mother's mayoral pardon and leverage on the pirate. He's as much right to the place as them with all their important meetings and planning sessions that take over the diner every time the town goes to hell.
Candlelight flickers inside jars on the tables scattered on the diner's patio. He pulls his left hand from his pocket to check his watch, and sure enough, it's after dinner time. Shouldn't be too many people inside then. Good chance he'll be able to get a booth instead of having to sit at the counter. The blinds bang against the door as he pushes it open and the first thing he sees is a familiar blue coat hanging on the coat stand. She's here. He stands in the doorway, still holding the doorknob, and scans the room for her. There, at the counter. Of course.
"In or out," one of the waitresses says as she walks by with a steaming tray of food.
"In," Will says, stepping over the threshold and closing the door behind him. He keeps his jacket on, he's going to need what's in his pocket, and walks to the far end of the counter.
She's tracing patterns in the half formed water rings on the counter top, ignoring him and the rest of the diner. He sits on the stool next to her and frowns at the rude hissing sound the padded top releases. "Bloody seats," he mutters, pulling an empty coffee cup and saucer toward him with one hand as the other unscrews his metal flask below the lip of the counter.
Her fingers flex, still splayed over the design she's sketched. For just a moment he thinks she might magic him to the far booth rather than suffer his presence.
"Sit elsewhere," Regina says, her words flat and sharp.
He knows enough of this woman to heed a warning sign when he sees one, and if the tense curve of her shoulders weren't enough, the careful angle of her hand still hovering in the air is more than enough. Nevertheless, he says, "I'm quite comfortable here, thanks."
"You have a nasty habit of making yourself comfortable where you're not supposed to be."
"Am I supposed to know what that means?"
"Maleficent is an old friend," she says, turning to look at him, lip curled, eyes narrowed. "She doesn't ask for favors lightly."
"And what favor would that be?"
"Plastering your Merry Men's faces on wanted posters throughout my kingdom." She tilts her head, considering him as though she's never seen him before, and while they've not had a lot of contact with each other before, during, or after her curse, this is the first time he's spoken to her one on one, he realizes. "I do hope stealing that looking glass from her was worth all the trouble it caused your friends," she says.
He shrugs. Pours a generous amount of spirit into the cup and salutes her. "To the things we'll do for love."
She scoffs and returns to pushing the condensation across the counter with her fingertips. "What do you want?"
"Can't a man enjoy a cuppa at the local dining establishment?"
"I think the Rabbit Hole may be more your speed."
"Well if you'd care to join me there, I won't say no," he says, knocking back the contents of the mug. More amber liquid falls into the porcelain from his flask. "But I have a message to deliver, and seeing as how I promised to deliver it, I am here, with you, instead of getting meself drunk all by me lonesome."
"What are you talking about?" Regina shifts, her arm resting on the counter to brace herself as she turns toward him. A whiff of apples tickles his nose before fading into the diner's greasy cacophony of smells.
He clears his throat, straightens the sleeves of his jacket. "'Will,' Robin says, 'Make sure she doesn't lose hope, because the darkness eats at the corners of her soul, and that's a terrible thing to fight against when you feel alone'." He drinks from the mug again. "And that is a direct quote."
Her lip curls again, an oddly disjointed action this time, as if she can't decide to smile or sneer. "Villains don't get happy endings, and they certainly don't have the luxury of dealing in hope."
"Right ray of sunshine aren't you?"
She shakes her head. "Don't tell me you don't see me as a villain."
"Doesn't really matter what I see or don't. Matters what he sees." He twists the flask's cap in his hand, scraping his thumbnail against the grooved edges until his finger goes numb.
"You think he was a fool for choosing me over Marian?" she asks, her voice lowered as the woman working behind the counter stacks newly washed glassware on the counter in front of them and then quickly moves away.
"Of course he's a fool. The bloody man's in love with you."
"For all it mattered in the end."
He leans over on his stool, gripping the counter to keep his balance. Close enough to smell traces of laundered clothes and those apples again mixed with something sweet, maybe cinnamon.
"Of course it matters," he says.
She pulls back from him, eyes wide, startled by his invasion of her space, and then he smells a burst of smoke, as if someone's struck a match, and he thinks this is it, she's going to roast him in the diner in front of everyone, but then he sees the waitress walking by shaking something in her hand and of course, the blonde has just gone and relit a candle that's burned out on one of the tables.
He leans back slowly. "True love isn't that easy."
"You call that easy?" Her hand slams onto the counter. "His wife came back from the dead, from my dungeon, in a time portal that defied the laws of magic."
"And how many years did you spend sending Snow White and Prince Charming running in circles 'round each other in the Enchanted Forest? Cast a curse that separated them for three decades? Tried to kill them multiples times using an increasingly creative range of methods? Ring a bell, Majesty?"
"You're terrible at pep talks. Please, leave."
"If you'd wanted to be alone, you wouldn't be at a public restaurant. Have a little faith." He pours the last of his flask into the mug, but leaves the cup nestled on the saucer. "Because if there's no hope for you, I don't think there's much for me either."
A small crease materializes between her brows as she frowns at him. She's unaware of his past beyond the theft of Maleficent's looking glass and his association with Robin, it seems, and that suits him just fine. He's not here to delve into his past, just hers. He reaches into his jacket pocket and pulls out a small pile of damp, wrinkled paper and places it on the counter.
"Don't set it on fire," he says. "At least not til I'm out of range."
"What makes you think I want that?"
"I get it. I do. The love of your life is ripped away from you and there seems like nothing to be done about it. But this," he says, stabbing the torn page with his finger. "This is magic. This is something beyond you and him."
She's gone quite still, staring at the pile of shredded paper with such concentration he's sure she's not actually seeing it anymore. That or she actually is about to immolate it, in which case he wants to be as far away as possible.
He stands and shrugs his jacket into place. "Have one on me," he says, pushing the cup toward her.
She glares at him, but slides the vessel closer with her fourth and fifth finger on the edge of the saucer.
As he's walking to the door, he sees a small flash of purple reflected in the window and catches her hand falling back to the counter where the remains of the page had been seconds ago. He hopes she's just sent it to a safe place and not destroyed it, out of sight, out of mind for now until she can face it again. Once he's outside the diner, he reaches into the other pocket of his jacket and pulls out the picture of the Red Queen he'd torn from the book in the library. He stares at the drawing for a long moment before carefully refolding it and tucking it back in his pocket.
Thanks for reading! My knowledge of Will Scarlett comes only from what I've read on the wiki online and his appearances in OUAT in season four, so apologies for anything overtly out of character. I missed the entire run of OUAT Wonderland.