Y/N meets Dean for a date after his semi-finals win, after some convincing. Dean is warned about what happens to those who fight the plan.

Characters: Y/N, Jo, Claire, Dean, Bobby, Uriel, Raphael

Warnings: threats of violence, past relationship abuse trigger (separate from the first warning)

Word Count: 2500-ish

Note: This one wrote a lot quicker than the last installment, which you can read here: Part 1 – Ringside. Please let me know how you like, or why not, and any guesses as to how it’s gonna go. If you like my style, my requests are open! Be on the look-out for a few coming out soon. Now, enjoy…

“You have to go!” Claire looked at Y/N, incredulous that her roommate didn’t want to show up to her date. “He’s going to the semi-finals… he’s hot! Why don’t you want to go?”

“It was an off-hand promise,” Y/N groaned, sinking onto the couch. “I didn’t know he was a… the boxer. I thought he was just some guy trying to get a date. Then in the hype from the fight, we set a place and time. I’m thinking clearly now.”

“No, you’re not,” Jo said. She hung a series of dresses on the door. “You’re panicking like every girl does before a date.”

“But you know what happened the last time I did something like this…”

“This is a different guy.” “A new start,” they said, overlapping one another.

Y/N looked back a forth between Jo and Claire. They were going to make her go, even if it meant they had to drag her there. A new start. “Fine, I’ll go.” She stopped their triumphant grins by pointing at the dresses. “I don’t know why you brought all those out; the one I wore to the fight will be fine.”

“Oh sweetie,” Jo said, dragging Y/N to her feet, “you are going to look perfect for tonight.”

“Trust us, looking pretty isn’t for the guy. It’s a real self-boost and since you’ll be wearing one of mine or Jo’s dresses, you won’t have to worry about ruining an outfit with bad memories… ouch!” Claire rubbed her arm where Jo slapped it.

Y/N laughed as they chattered plans between them, then waited for her input. They were good friends. Y/N wouldn’t have anybody else looking at her, waiting to hear her ‘okay’. If this did go sideways, they would know how to help her through it.

“Alright then. Let’s get going.”

All three of them squealed as Jo and Claire started to dress her for the night.

The summons was almost as ominous as Dean thought it would be: a quick call with a single command. He attempted to walk quietly through the arena, but his steps continued to echo through the dark space. Raphael’s office provided the only light, shining from one corner of the rafters except for two dark forms moving on the inside. Bobby was waiting for him at the door with a heavy pat on the back but didn’t enter with him.

“Winchester,” Uriel sounded surprised to see him, “sit down.” Dean sat in the only available chair, which was situated in the middle of the room. Uriel started to pour a drink with his back turned to Dean. Dean knew it wasn’t for him. Uriel took it instead to Raphael, who was leaning against the windows in the far corner.

“You know why you’re here?” Raphael asked, wafting the glass under his nose. Dean could smell the aged brandy from his chair.

“Are you the principle now?” Dean snarked.

“No. I’m your boss.” Uriel sipped the drink slowly, keeping his voice low and dangerous. “And when I tell you to lose, you lose. Not that KO from last night.”

Dean shifted in the chair. He’d never met Raphael in person before, but he didn’t like it.

“We lost money last night, Winchester,” Uriel chimed in. “I want to take it out of your hide, but Raphael’s got a better plan.” Uriel poured himself a shot of whiskey and downed it quick, snarling through the burn.

“Cole gets a rematch.”

“What? You son of a ” Dean tried to stand, but Uriel pushed him back down and kept his hand clamped over Dean’s shoulder.

“A rematch. I’m leaving it up to Cole to figure out the particulars of why he wants one, but it’s also your second chance. If you follow orders like a good little soldier till then, I might let you keep your win. Otherwise, I’m going to tell some of the more obedient players to give your brother a visit.”

“Leave Sam out of it.”

“Can’t do that, Winchester.” Uriel squeezed Dean’s shoulder harder, then left to sit on the edge of Raphael’s desk. “When one of the team messes up, it ripples through the whole operation.” Uriel stood to his feet under Raphael’s glare.

“What’s it gonna be, Dean? You can win either way if you play along.”

Dean gripped the arms of the chair, almost wishing he could hear them splinter if he squeezed hard enough. But he relaxed his gaze and loosened his grip. “What’s the script?”

“We’ll tell you when it’s time.” Raphael nodded to Uriel, who grabbed Dean by the arm and pushed him towards the door. Dean had his hand on the knob when Raphael laughed. “See, following orders isn’t too hard.”

Dean turned to growl but kept moving instead. When Bobby wasn’t outside, he left the door open, relishing in Uriel’s harsh curse.

---

She knew she was early, but every minute felt like an eternity. The table for two by the jukebox was empty, reserved with her name on a tented piece of paper. She laid it flat at first, but now she was fiddling with it till it was shredded. Again, she checked the clock on the wall. He wasn’t late, yet, but damn did it feel like it. Did he have the same idea to skip out? He couldn’t, or the table wouldn’t be reserved. Right?

“Did he stand you up, doll?” A well-dressed man sat in the other chair, looking very much out of place. His grin was not unpleasant, but it was too big. Too bright. “What’s your handle? I’m Richard.”

“None of your business. I’m waiting for someone.”

“And he’s late. His loss.”

“Actually, he’s still got a while. I’m early. Your miss.” Y/N turned to face away from him, hoping he’d take the hint. Instead, he reached across the table and took her hands in his, gripping them tightly so she couldn’t get away.

“But a lovely girl like you shouldn’t be waiting alone, and not without a second opinion.”

“The lady said to get lost. Sorry, I’m late.” Dean yanked the man to his feet. Richard straightened his jacket as they stared each other down.

“Actually, you’re right on time.”

Richard twisted his head, “Dean ‘Raisin Cain’ Winchester. Out of the kennel for the throw last night?”

“Shut your mouth, before I kick it wide open.”

Richard chuckled, “what? You don’t want your girl knowing it’s all planned to a tee? A scam. A fake.”

“You want to see how real it is? Take a step out back and I’ll show you.” Dean and Richard grabbed each other by the lapels at the same time, but Y/N jumped to her feet and pushed them apart. She pulled Dean to her side of the table and wrapped her arms around his waist, positioned to defending and being defended by Dean.

“I’m not interested in seeing him bloody you, sir. I’m not interested in you at all. So get moving.” Her heart hammered in her throat as Richard grunted and walked out.

“If you squeeze any tighter, darlin’, I’m gonna get bumped down to a middleweight.”

Y/N let go of his waist, “sorry. I just ruined my chance, didn’t I?”

“Not at all. That was wonderful,” Dean laughed. “Just remind me if I get too big for my gloves that you could KO me in a heartbeat.” He helped her into his chair before hanging up his coat and hat and joining her. “Does that always work?”

“It didn’t at the fight, thankfully. It comes from a promise I made to myself.”

“And what was that?”

Y/N grinned, “stop being a polite doormat.”

Dean gave her a thumbs up and sighed. They sat in silence till Dean asked, “Hey! This is a date, isn’t it? Do you want dessert first or last?”

“Please?” Y/N thought back to some of the phrases Jo and Claire had taught her. Was this one of them?

“This place has the best pie in Illinois. Sometimes I eat it first so I don’t run out of room, but if that’s too strange we can wait.”

“No, that sounds perfect.”

“Alright, blueberry or cherry?”

He was a comical sight. Y/N could tell he wanted to wolf it down while it was hot, but he ate slowly to stay neat. In the meantime, she learned more about him, and he learned more about her. Just the basics. The dinner slowly emptied out till there was only the cook and the bar. By the time they ordered and their main meal came out (burgers with a slice of pineapple!) they were joking like old friends, but she could tell he was holding something back.

“Just spit it out, Dean.” She giggled as he looked around confused after having taken a huge bite of his burger. “Not the food, the question you’ve been holding back on.”

Dean nodded and swallowed, but thought about it for a minute longer before trying to throw it into the air. “So, I get the moving away from home and the freedom and the roommates. But why Chicago? You sound too high-class to be living on this dark side of town.”

It took her by surprise, deeper than the rest of the questions. She took a breath and tried the usual brush-off. “Chicago was less expensive than New York, so here I am.”

“No, it’s more than that. I’ve seen… I’ve had that face before. What are you running away from?”

She nearly choked on her drink. But his eyes were attentive and deep. And don’t get lost Y/N, or he’s going to think you’re crazy. “It’s not a what. It was a who.” She shrank back into her chair, questioning if she was really going to tell him. He reached out for her hand, and she gave it to him. The warmth and the small squeeze spurred her on. “Honestly I didn’t want to go to the fight. I thought I’d had my fill of seeing punches thrown.” The next words died in her throat, refusing to leave.

“I know the feeling.”

Y/N looked up at him, surprised. He nodded and looked away, but didn’t add any more. He didn’t have too. He gave her hand another squeeze then stood in front of the juke. Dean had paid enough to keep it going all night, but he switched over what was playing to one of Sinatra’s new albums. Come Fly With Me began to spin, crackling to life as trumpets started the tune. He pushed as few of the tables out of the way before pulling Y/N to her feet. He started swaying slow but picked up the pace as the music hopped.

By the time Moonlight in Vermont rotated in, Y/N was as close to him as she could be with their clothes still on. He led the way, turning her and swaying while humming along. But she couldn’t help but feel the questions bouncing around in his head as his back stiffened and he swayed out of time.

“What’s on your mind?”

“Hmm?”

“You’re stiff.” She smiled into his tie as his steps faltered, making a note to thank Jo. “You’re not swaying to the music as you were,” she continued. “Something in your thoughts is blocking your steps. Do you want to talk about it?”

Dean considered it. But she was too new, freshly escaped from other problems. She didn’t need his. Her voice broke through his wonderings.

“Say what you can. Your heart will follow.”

Dean spilled in one breath, “what would you do if… have you ever… I mean… ugh. I’m not very good at this.” Dean stopped swaying. Y/N placed her hands on his chest. They were so small and delicate. He couldn’t break her. “I’m sorry; I can’t.”

“That’s alright. But you still need to talk to someone. Somebody you trust.” Y/N ran her fingers under his tie, searching for anything comforting. “I talk to Jo and Claire about anything I’m not sure about. And I’m just a phone call away.”

Dean perked up. “Are you offering to give me your number?”

Y/N blushed. “Yes. But be warned, it’s a party line. It’s probably worse than getting spied on by the police.”

“Hey, mine is too. Same boat.”

“Miss?” the bartender interrupted the moment, and Y/N realized she was again pressed up against Dean.

“Yes,” she said, stepping back.

“There’s a call for you. A young lady named Jo?”

“Oh.” Y/N looked at the clock. It was half an hour later than when she’d said she be home. She ran over and took the receiver. “Jo?”

“How are you still there? We figured you’d be home or elsewhere by now.” Y/N heard Claire giggle in the background.

“Sorry. We were, um,” Y/N turned to face away from Dean, “we were dancing to Sinatra.” She heard him snort and start to gather their things.

“Alright. Will we be seeing you tonight?” Now they were both giggling.

“No. I just didn’t realize how late it was. I’ll be home shortly.” She ignored their teasing and hung up. The waiter waved away her coins with a smile and continued to clean up the bar. “It seems I am late for curfew.”

“I’ll call you a cab.” He nodded to the waiter, who nodded back and dialed. “And before we get interrupted again, what’s the number?” She laughed and wrote it on a napkin before sliding it into his coat pocket. He wrapped her shawl around her shoulders and led her to the door. They stood in the window until the cab honked. Dean handed the cabbie his cash, despite Y/N arguing that she could pay her own way.

“What about you?” she asked, leaning out the window.

“I walked here; I’ll walk back.” He chuckled at her worried face. “I’m Dean ‘Raisin Cain’ Winchester. I’ll be fine. And I might take your advice. So, thanks for that.” The driver started up his motor. “And Y/N, thanks for coming out.”

“Thanks for asking me.” She blushed and peaked at the driver. “I hope we can do it again soon.”

“I’ll call you.” He waved after her as the cab pulled away. His apartment could have been a block away or fifty. He didn’t care; every step felt like it was on air. As for Uriel and Raphael… well, he pushed them out of his mind. They could wait till daylight. Their damned plans weren’t going to bring him down now.

---

Y/N sprawled out on her bed still in her roommates’ date dress. Jo and Claire were whispering like giddy snakes in the living room, waiting for her to regale them with everything. But first Y/N wanted to remember the way he felt pressed against her, the way he smelled, his smile.

What couldn’t he tell her?

She sighed the question away. When he was ready, he’d say something. And maybe, if her luck held out, she could tell him things too. Things she hadn’t even told Jo or Claire.

Part 3: Undercard 

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