It was Thursday now, four days after his initial meeting with Castiel and Dean was significantly worried. Rejection was eminent and was most definitely not something he dealt well with. He had told Jess about his plan and she was probably the only reason why he was even entering the café now and not just turning around and leaving.

Dean Winchester did not get nervous.

Except around Castiel Novak.

Yeah. It sucked.

The bell dinged as the three of them walked in and Dean felt a mixture of relief and severe disappointment when he saw that Castiel wasn't seated at his usual table. His shoulders slumped and he debated not just exiting the shop right now.

"Can I help you?" a gravelly voice asked from the counter, a happy lilt accompanying its normally neutral timber. Dean's head swivelled to look at the source and felt his heart swell just a little.

Not that he'd ever admit it.

"Cas," he said, a smile threatening to split his face in two as he walked over to the counter and slid into one of the stools lining it without hesitation. "Why are you working today?"

Sam and Jess came up behind him as well, equally surprised to not be greeted by Gabriel. They had been used to seeing the short trickster for almost two years now every morning so it was little odd not to see his scheming grin.

Cas shrugged as he filled up a jar with sweets. "Someone broke into our supply of salt yesterday and spilt it everywhere. Took a container too. So he went out to get some more."

Sam began to edge away from the conversation. Jess shook her head in exasperation and ordered for the two of them.

While Castiel was busy preparing their orders, Dean went through his game plan for asking out the blue-eyed man. He still wasn't sure about the guy's orientation so he didn't want to make it seem like a romantic affair, though he hoped it was one. For all he knew though, Castiel was very much a straight man.

Damn, he should have definitely asked Gabriel before going through with this mad plot. Unfortunately, the shorter man wasn't going to be around to ask today and this was his one chance.

"So how are you today Dean?" Castiel asked as he handed him his pie, still warm from the oven.

Dean jumped at the intrusion to his thoughts and replied quickly, "Good! Never been, uh, better… you?"

"Fine thank you," he said smiling. "Though I'm a little disappointed that I couldn't be reading today."

The blond swallowed and took a large gulp of his still hot coffee. The burn of it seemed to centre him a little more and he asked, "So you really like those Russian novels right?"

"Yes, I believe we already established that," Castiel frowned.

Dean tried to smile but it might have looked a little pained. He hurriedly nodded and continued, "Right, right. Have you ever read Taras Bulba? By Nikolai Goggle."

Oh God, he'd done it. Well not really but he'd started it. What if Castiel hadn't read it? Or what if he hated it? What would Dean do then?

Finally, after what seemed like an eternity of waiting but was probably only a few seconds, Castiel responded. "I think you mean Nikolai Gogol, but yes I have," he replied, eyes a little unfocussed as he remembered, "I read it a few years ago. I very much enjoyed it. Why?"

His eyes were narrowed as he looked at Dean, "What are you planning?"

Dean felt a little more confident after jumping that hurdle but it was still in a nervous rush that he asked, "Wellwouldyouliketogoseeitwit hmebecauseitsplayingatthelaw rencetheatretonightatsevenan dnine."

Castiel blinked. "Pardon me?"

He took a deep, steadying breath and tried again. Slower.

"It's playing at Lawrence Theatre tonight at seven and nine so I was wondering if you wanted to go see it. Together. Platonically."

He could have slapped himself for that. Platonically? Honestly, he was a bumbling idiot.

Castiel, however, didn't seem to notice Dean's inner chastising but was instead beaming at him. "I'd love to."

Dean smiled back and was about to say something else when Sam unceremoniously dragged him out of his seat and towards the door.

"Great, I'll pick you up here at seven then," he called as he fended off his brother's large hands.

"I'd prefer nine!" Castiel revised quickly. "I close at 8:30."

Dean nodded and waved goodbye, still grinning like an idiot.

As the next patron entered the shop, Castiel couldn't help but comment on what a wonderful day it was.


Jess was lying on Deans' bed staring up at the ceiling. Actually, if you looked hard enough, there was a likeness to wings on the chipped plaster of the roof. Not really bird wings though… more like angel ones. Although, that was ridiculous.

"Dean, why am I here?" she questioned, lolling her head back until she could see the man standing upside down in front of his dresser. He was frantically rifling through his drawers, holding up different pieces, analysing them and then throwing them away. He didn't appear to hear her as he studied two identical button downs.

Ever the resourceful one, Jess picked up one of his pillows and chucked it at his head. "Hey, Winchester! Are you listening to me?"

He whirled around to face her as the soft projectile hit his back with that same crazy look that Sam had adopted shining in his eyes.

She was seriously beginning to question her choice of housemates.

"What?" he snapped, his hands scratching at his bare arm reflexively.

Jess sighed and rolled onto her stomach, "Why am I here Dean?"

"'Cause you're a girl!" he cried, throwing his hands up in the air as if it was the most obvious and exasperating question he had ever received.

She rolled her eyes, "Oh well thank you for noticing but why does that mean I have to be here."

"Well you know. I'm not good at this chick flick getting-ready montage crap and you know about all this girly shit so…"

"Is that really your way of asking for help Dean?" She asked with a raised eyebrow.


Jess heaved a sigh, "You really are a man-child."


"Do you want my help or not?"

"…Yes… but do you have to insult me at the same time?"

The grin she flashed him was truly frightening, "Consider it my reward."

Dean stared at her for another moment before shrugging. Trust Sammy to find all the crazy, sadistic ones.

"So what do you need?" she asked, sliding off his bed to stand next to him.

They both looked around the room, which was covered wall to wall with the flung out contents of his entire wardrobe. "How about something to wear," he finally suggested with a wry grin.

The blond girl laughed and began rummaging through his clothes. She picked out a nice suit jacket that he had worn to some distant cousins wedding and held it out, "this one's nice."

Dean's eyes widened and he shook his head, "No way! It's too fancy; he'll think we're on a date!"

She raised an eyebrow, "Well aren't you?"

"No! Yes… maybe?" Dean said, scratching his head before sighing in defeat. "He just doesn't know it yet.

Jess sighed and put down the jacket. "Dean, Dean, Dean," she tutted, "I thought you asked him out on a date."

"Er yeah I did. Platonically," he confessed with obvious disgust in the word. "I panicked. I didn't want to make it seem like a romantic thing in case he was straight."

Her blue eyes widened, "Wait, you don't even know if he's gay."

"Uh, no," Dean replied, rubbing the back of his neck.

"Oh for the love of God," she said, face palming. "Ok, new plan. Figure out his sexuality tonight before you try anything with the guy. I don't want to see you get hurt again Dean," she said softly.

He looked away.

"As for the clothing, I vote for the green button down, dark jeans- no holes Dean- and that leather jacket you're so fond of. That's low key but nice enough for some foreign flick."

The look of relief in his green eyes was almost comical to Jess. She was an only child but Dean felt like a brother to her and she liked that familial bond. It was with giddy excitement that she realized soon they would be officially siblings. Chances were she'd probably regret it later but might as well enjoy the idea before it became reality.

As Dean was changing in the bathroom, Jess reflected on her soon-to-be brother's love life. He had come out as gay on his eighteenth birthday and was promptly kicked out of the house. Sam had wanted to follow him but ended up staying with his father for two more years before he ran away to live with Dean. The two had been inseparable since, wherever one would go, the other would follow.

After she and Sam moved in together, Dean had tried to get his own place but ended up spending almost all of his time in their apartment anyways. Finally they just offered him a room in the new house they were about to buy together and he accepted. This was only after some angst of course, because suffering and Winchesters were practically synonymous.

Dean had never been lucky with relationships though and, more often than not, they turned toxic for both parties and they would split. It hurt her to see one of her best friends struggling on alone, constantly trying to convince himself and everyone around him that he was happy. She hoped Castiel would be different, better. He was certainly different from any boyfriend Dean had ever had before.

"So, uh, why Castiel?" she called from her place on his bed, inspecting her nails. She should probably paint them soon.


"Well, he's not your usual type."

Jess could practically see him shrugging as he replied, "I don't know. There's just something about him… it draws me in, you know? He's smart and funny, in a kind of subtle way. He has the best poker face ever- I mean the guy could make a living in Vegas- but his eyes can be so… expressive."

"So it's not just his ass then?" she smirked.

"Jess! I can't believe you would ever accuse me of being that shallow!"

The blond girl laughed.

"… Although he does have an excellent ass," Dean admitted with a grin as he walked out of the bathroom. "So what do you think?" he said, turning slowly.

She smiled and nodded, "Perfect. Now time for the hair."

"What's wrong with my hair?" He asked with a defensive edge and reached up to touch the cropped, blond strands.

"Oh Dean," Jess sighed, "There is so much to teach you."

And then she advanced, armed with a comb in one hand and gel in the other.


Meanwhile, Castiel was manning the almost empty café with a decidedly dreamy expression on his face as the outing drew ever closer. Normally, he wasn't one for indulging in the land of what might be, but thoughts of Dean were still very much at the forefront of his mind.

He didn't look up even as the bell dinged in the café, only glancing over when Gabriel's loud voice sounded across the near vacant store. "Hey Cassie!" he hollered, carrying a large box, "I got me some sodium!"

Castiel rolled his eyes and smiled at his cousin, "I'm glad Gabriel. I can hardly contain my joy."

"Whoa ho ho! Was that a joke I heard from little Cassie?" Gabriel questioned as he set down the box. He brushed a fake tear away from an amber eye, "They grow up so fast."

The blue-eyed man chose not to respond and just picked up the box to carry into the back of the store, averting his eyes from his cousin. "Gabriel, I won't be able to stay late tonight."

"Why not?" the shorter man frowned and followed his cousin into the storeroom. Castiel had always been able to stay late.

He cleared his throat, a sure sign of discomfort in Castiel. "Well, uh, I've worked the store all day!"

"So?" Gabe narrowed his eyes. "That's never bothered you before."

Castiel looked around the shelves, trying to find inspiration. When it didn't strike him, he answered lamely, "Uh… well it does now?"

"Seriously? You could care less about your work hours. Apparently the 'monotony' helps you think, remember? Now what's this really about?"

"Fine," the younger man submitted with slumped shoulders. "Dean and I are going to see a movie tonight and-"

"Oh!" Gabriel interrupted with a gleam in his eyes. "You, Dean and a movie? I see, you want to spend some time with your man!"

Castiel frowned, "He's not my man…"

"So this isn'ta date?"

"I don't know," he replied, his tone laced with frustration. "Dean is a very confusing individual, I'm unsure of what he wants. He never mentioned this being a date."

"But he did ask you?"


"To go to a movie?"




"Just two single bachelors who have known each other for less than a week and constantly have eye sex across my clean tables."

Castiel gave him an annoyed look, "I hardly think that is appropriate or accurate."

"Fine, fine," Gabriel waved his comment off. "But if you're going to go on this date-"

"Not a-"

"- Alright! If you're going out on this excursion, then I'm going to have to give you a few pointers."

"Like what?" Castiel asked, eyeing his cousin warily.

"Well, to start with, you're going to want to engage in some good conversation. A bit of witty repartee to avoid any awkward first excursion lulls. Just try to joke around, flirt a little."

Castiel looked visibly troubled. "I don't know how to flirt."

"Don't sweat it," Gabriel grinned, throwing an arm around his cousin's hunched figure. "Just joke around, be a little suggestive and try to get in his personal space whenever possible."

Castiel considered this. "Perhaps I should make a list?"

Gabriel just shook his head and opened his mouth to say more when the bell inside the store dinged. They were both still in the storeroom so they couldn't see what confused customer just wandered into their closed shop.

They both froze, however, when they heard a familiar voice call out, "Cas? You in here?"