Archive of Our Own ^beta

Part 1: To This Great Stage of Fools

When Dean first took this prestigious gig at Edlund University, he thought the hardest part of the job would be the students.

Here in New York City, a stone’s throw from the West Village, he’d imagined getting a roster of thirty or so trust fund babies with Entitlement stamped across their foreheads and boredom in their eyes.

While that brand of lazy smartass did enter his classroom by the small handfuls every semester, most of his classes were made up of shiny-eyed baby adults just trying to find themselves. Of course, there were some of them who thought Chat-GPT could solve all their problems—including shitty writing, worse notetaking, and the short-term memory of a goldfish.

But Dean could deal with all that. He found ways to grab and hold their attention with stories, not to mention his own brand of real talk from time to time.

What actually chapped his ass the most?

Faculty meetings.

At 7:30 a.m. on a Monday, he had to sit in a sea of bedraggled professors running on the remnants of “weekend time,” rolling over into a new work week, inching ever closer to Thanksgiving Break. Before his morning coffee even set in, he had to listen to Dr. Crowley drone on about the spring budget in a 30-slide PowerPoint presentation. It was downright inhumane.

But the guy was now the academic dean over two schools: Arts & Sciences and Business. The university was small enough that when the previous Dean of Business left the school last year for personal reasons, Crowley convinced the higher ups of Administration that he could take on the position in the interim, another large feather in his cap.

He seemed to think that made him God.

“As you can see, we will need to trim the spring budget by 4.6% in other areas if we’re to accomplish all the renovations that we have planned for the Business School next year,” Crowley said. He kept his laser pointer trained on the graph featured on the large screen. Everyone else had handouts of each graph with about ten pages of bullet points, front and back.

“The question is, from where can we trim the fat?” he posed.

He was met with silence. Chairs squeaked from shifting butts in mildly uncomfortable seats. Marv covered up a dry cough from his asthma.

Dean slurped his coffee, a free cup of the slosh they’d served before the meeting. Benny glanced over at him, barely hiding his amusement. The two of them sat together with Cas, over to the left of center stage in this classroom in the Business School. It was big enough to hold almost fifty faculty members, as well as a giant smart TV mounted on the wall. Was it really a mystery why they were over-budget?

“Why are we talking about next year when we haven’t even made it to Thanksgiving yet?” Dean muttered to Benny. He was the History department Chair, so he handled the administrative shit that would drive Dean up a wall and into a handbasket.

“Because, Professor Winchester, we aim to break ground on the east wing by spring,” Crowley said pointedly. “You all have been overspending, from birthday lunches on company cards, to new computers and iPads. We have an IT department for a reason, people! Make sure your devices are being maintenanced on a regular basis. If it breaks down, you will now pay the cost of replacing them.”

That caused a rumble of protest among the faculty. The only group that didn’t look ruffled was Dick Roman and the rest of his posse repping the Business School. They sat leisurely with their pressed suits and feigned interest that masked a veneer of boredom. 

Dean was more of a jeans, boots, and flannel kind of guy. He dressed it up with a leather jacket at this time of year, but it was more for warmth than a fashion statement.

He took a cursory look at the “spring plan” and raised a brow.

“Does the Business school really need three office renovations, four $20,000 smart screens, and another $500 espresso machine?” he said. “Is that for the students, or so the faculty can get their fix without having to slum it with us commoners in the teacher’s lounge?”

That earned him quite a few head turns, but also more murmurs from the faculty.

It also got Dick to draw himself up in his seat, his arms uncrossing.

“Our Business School has the highest enrollment rate across every department represented here. It’s the university’s biggest draw, which makes it crucial that our offices and classrooms offer the right caliber of resources, opportunities, and amenities for students and faculty,” he said. His gaze then homed in on Dean. “Not to mention, it increases a sense of professionalism that seems to be lacking from other departments.”

“Quite,” Crowley added dryly. He focused his laser pointer on Dean’s boots that rested on the empty desk in front of him. “Do us a favor and get your boots off the table. This isn’t the Golden Corral. This isn’t community college. It’s a university. And to Dr. Roman’s point, we could all stand to tighten up around here.”

Crowley glanced at Dean’s old jeans and the drying coffee stain on his gray undershirt with thinly veiled disdain, but he continued with the rest of his presentation.

Dean felt a small prickle of embarrassment at being called out in a room full of people who had at least ten to twenty-five years of experience on him, with many of them now looking at him like he was some country hick. He might be from Kansas, but that didn’t mean he had no class.

He slid his boots to the floor and sat up a little straighter.

The meeting was adjourned after an hour, letting Dean, Benny, and Cas plot their lunch plans on the way out of the conference room.

“How about the burger spot?” Dean said.

“We go there twice a week. I feel my arteries clogging with every experience,” Cas said drolly. “How about Alley Cat? It’s new.”

“Alley Cat? What the hell do they got there?”

“Sushi.”

“And hibachi,” Benny added.

Dean shot him a grimace. “Aw, not you too. The appeal of raw fucking fish is lost on me.”

“As are most things of sophistication,” Cas remarked.

“All right, Garçon. You into eating the little fish eggs too, with a side helping of squid testicles? Jesus, it’s like Finding Nemo,” Dean groused.

Benny chuckled. “Not sure that was the Pixar version, chief.”

They managed to follow the crowd out into the hall, where the other professors dispersed. All three men had classes in the next few minutes. Cas taught Hebrew, Latin, and Greek in the foreign languages, while Benny taught specialty topics in World History.

“Professor Winchester,” Crowley called out.

Dean paused and looked over his shoulder, holding in a sigh. Crowley was standing by the double doors with a beckoning hand.

“A moment,” he said.

“Great,” Dean muttered under his breath. He tossed his friends a knowing look, and Benny bumped a supportive fist against his shoulder.

“Sayonara,” he said, hinting at a smile.

Hilarious. Dean shook his head and went back to meet up with Crowley. He stood there in the same suit he wore every day in different color variations. This one was dark gray, paired with a red tie.

“Walk with me,” he said.

Dick Roman and the other men from his department were the last to pass by. Dick himself wore one of his signature smirks that boasted superiority and Botox. He gave Dean a fleeting glance, but kept walking like his polished Italian leather shoes were made to own these halls.

“I’ve finally had time to go through the student evaluations from last spring,” Crowley said.

“Aw, they don’t even bother to fill those out,” Dean said. “By the end of semester when those roll out, they’re running on latte fumes and questionable cafeteria food. But seriously, someone should look into that, because I got indigestion at the salad bar.”

He mainly went over there for toppings to add to his pizza, but his point still stood.

Crowley ignored him though. “You actually receive the most student evaluations of any professor under my domain. And do you know what they consist of?”

Dean paused, both surprised and kind of flattered. He never really bothered to check those evaluation reports, even though he had access to them.

He smiled to himself. “That I’m awesome, I guess.”

Crowley withdrew an iPad from under his arm and pulled them up on the screen.

“‘He’s a chill dude who doesn’t make us do a lot of work,’ according to Jessie,” he said dryly.

“Jessie? He was a freshman in Humanities I. Everybody has to take that class,” Dean argued.

“Does that mean it should be a free for all?” Crowley retorted. His eyes returned to the screen. “Next one, from Carmen: ‘He’s so hot, I couldn’t even function.’”

 Dean tamed his smile, almost rolling his eyes. That girl barely blinked in his class. Sometimes he didn’t know if she was spacing out or sleeping with her eyes open.

“Oh, that amuses you, does it?” Crowley said, his brows raised. “How about this one from Kevin: ‘Good class, but I returned the textbook because we didn’t use it the whole semester.’”

Dean remembered Kevin. Good kid. Kind of a mama’s boy. Definitely an overachiever for an 18-year-old freshman. He asked Dean what he had to do to make up the points for getting an A- on a test. Dean just asked him a few extra questions on the spot. When Kevin nailed them all, like Dean knew the kid would, he changed the grade to an A.

“Why aren’t you using the assigned textbook?” Crowley demanded.

“Come on, man. That thing was published in the ‘60s,” Dean said. “It’s dry as hell, and these guys don’t read it anyway. So I figured I’d just riff in the lecture, give them the important points from the chapters and test them on that.”

Crowley huffed. He paused in the hallway outside his office, leading Dean to do the same. 

“If the students don’t think they have to buy the books, they won’t,” Crowley said. “Which means they won’t buy them from us, which affects my bottom line. Ergo, your paycheck.”

Dean crossed his arms. “Why don’t we get some better books then?”

“Because we have a contract with the distributor.”

“You mean you have a deal with ‘em. So what you’re telling me is that you’re willing to cough up $80,000 on some touchscreen TVs for Dick and his crew, but you don’t want to pay for a little upgrade on some textbooks? That’s real nice,” Dean said, a knowing glint in his eye. “It’s all about the kids, right?”

Crowley’s posture straightened defensively. “I suppose you didn’t have your ears open, but what Dick said is correct. The Business School has the highest enrollment rate at EU. Therefore, it makes the biggest financial impact, meaning the cost is worth the investment. It’s simple math.”

“Yeah, well, I failed Algebra. Letters and numbers don’t mix, far as I’m concerned,” Dean said. “But I got an A in Bullshit Detection.”

“Watch yourself, Dean,” Crowley’s voice sharpened. “Your brother may have pull here, but so do I. You wouldn’t want to embarrass his father-in-law, would you?”

Dean wanted to roll his eyes, but he resisted. He had that much self-control. Instead, Crowley gave him a pointed brow raise that said, Understood?

Dean nodded in annoyed resignation.

Satisfied, Crowley stepped back into his office, leaving Dean standing in the hallway.

Dean got back to his own office and sat down in his comfy leather chair, blowing out a breath of relief and exasperation. Today was already grating, and it wasn’t even halfway to lunch.

He opened up his school-assigned laptop and tried to turn it on, but after several seconds of staring at a rolling collection of little white circles, turning and turning on the screen, he realized the damn thing wouldn’t boot up all the way.

Of course.

He pressed the On button repeatedly, all but smashing it with his pointed finger, but that just made it worse. All that came up was the blue ERROR screen of death.

“Stupid fucking PC,” he muttered and reached for his desk phone, putting in a call to the IT crowd. 

“IT Department,” answered a bored voice on the line.

“Who is this? Gerry? I wanna talk to Frank,” Dean said. He frowned as he listened to the guy’s droning reply. “It’s 9:30 in the morning. What do you mean he’s out to lunch? …Okay, fine, fine. Get me Charlie.”

Without another word, he was transferred to the familiar bubbly voice he’d come to know.

“'Sup, Dean. What can I do for ya?”

“Hey, Charlie. My piece of crap won’t start again, and I’ve got a class in 20 minutes.”

“Well, don’t take it out on the computer! I can hear you banging on it like a steel drum. I’ll come by in a few minutes.”

“Thanks.”

Charlie soon dropped in to his office. After fiddling with his laptop for less than ten minutes, she had it running again. She turned it toward him with a triumphant smile on her face that said, Yeah, I’m awesome.

Dean shook his head in awe. “Damn. They’re not paying you enough.”

“Correct, but I kick-ass anyway,” she said. Though her gaze turned sly. “Looks like it caught another virus, but I cleared it out and reset the system. Crazy that it even made it through my firewall, unless you happened to be browsing something…shady. Unsecured.”

Dean paused while scanning through his emails. He looked up at her, where she stood on the right side of his desk with her arms crossed.

“I don’t know what to tell ya there. I just use this thing for work,” he said, clearing his throat.

Charlie patted his shoulder. A smirk played on her lips.

“All right, cool. Let me know if it craps out on you again. This thing is like, ancient. Circa 2014. You really could use an upgrade,” she said.

Dean snorted. Didn’t he know it. But he remembered Crowley’s little budget rant this morning. If Dean wanted a new laptop, he’d have to pay out of pocket himself. Whatever.

Charlie stopped in the doorway and peeked her head back in.

“Oh, just so you know, I can see everyone’s browser history,” she said with a knowing grin. “And nothing ever really gets deleted.”

Dean’s eyes widened, his jaw clenching. He didn’t have time to give any kind of denial or self-defense before she ducked out and closed the door behind her. He just had to stew in the hot sting of embarrassment.

He distracted himself by pulling up his notes for his first class of the day.

“All right, settle,” Dean said, projecting his voice above twenty-five freshmen in Humanities I who either couldn’t stop yapping at each other, or couldn’t get their eyes unglued from their phones.

“I’m not gonna tell you to lock up all those phones, but like I’ve said before, I’m not the one getting tested on this stuff next week. If you’re happy with a mediocre grade, that’s your business.” Dean pointed over to a girl sitting in the second row, probably scrolling through Instagram. “Like Alicia taught me last week: If you like it, I love it.”

She looked up from her phone, surprised to be called out, but she laughed and tucked the phone back into her pocket.

“All right, today we’re picking up from where we left off, talking about the British settlement of Roanoke in the late 1500s. In other words, the start of Colonial America.”

Dean was met with a sea of blank, unenthusiastic stares.

“Yeah, I know. Buckle boots and pilgrim hats. Real exciting,” he said.

Then, he smiled conspiringly. Time to turn it on.

“But remember how we said the first attempt at this little colony failed, and the second one was getting set up in 1587? Okay, well, the kind of interesting tidbit about this story is that their governor, John White, had to make a supply run back to the Mother Ship. AKA: England, ‘cause they were running out of tea and crumpets.”

That quip earned him a smile from Alicia, at least.

“When he got back to North Carolina in 1590, he found the colony mysteriously abandoned,” Dean said. “No explanation. No sign of anybody. Historians, archeologists—nobody knows whether the settlers moved on somewhere else, or if something just wiped ‘em all out, like a bout of influenza or a Native American tribe. The only evidence they left behind was a single word left carved into a post: CROATOAN…”

Benny knocked on his door around noon, but that was more to just announce himself as he stepped into his friend’s office.

“Ready for…lunch?” he asked. His voice trailed as his gaze travelled across Dean’s workspace.

His desk was buried again—this time by what looked like two large stacks of quizzes, among various other mystery stacks that piled haphazardly around his laptop. The filing cabinet next to said desk was merely an ornament propping up no less than three old mugs of coffee. Bookshelves spanned behind his desk, wall-to-wall, but only half of it was filled by books. More papers, manilla folders, and random office supplies were tucked in between.

And nestled against the wall was a simpler wooden table that propped up an old desktop computer, a wily wad of wires and extension cords, and an old ball of rubber bands. Underneath the table, on the floor, was a large shape underneath a black canvas tarp. Benny didn’t even want to know what that was, but this whole space was on the more tumultuous side of organized chaos.

“What the hell is happening here?” Benny asked. He gestured widely at Dean’s desk in particular. That was more than enough to focus his eyes on.

Dean looked up from his laptop, his dark brows meeting together in confusion.

“What?”

Benny thumbed through the closest stack of papers. “First of all, you gotta be one of the only guys I know who still makes these kids write things down, besides maybe Zachariah.”

Dean huffed. “Yeah, good ol’ Zach. I hear he gets a kick out of making ‘em write ten-page essays by hand. In cursive.”

He continued multitasking, writing an email and checking his calendar for how much time he had for lunch until his next class. “I dunno, man, I just hate staring at a screen all day. Plus, these guys need the practice. Their handwriting sucks ass.”

Benny heard him. He just couldn’t really pay attention to the words when he was making more discoveries. He unearthed a large packet of essays clamped together with a silver capo. Never mind that Dean didn’t even play guitar.

“You gotta be kidding me. You’ve got shit here from early August,” Beny said in disbelief.

 “So?”

“We’re in November, chief.”

“Don’t worry about it. I’ll get to it,” Dean said. He finished sending off an email to Registrar, promising he’d get his midterm grades in soon. He might’ve been a couple weeks late on that one. 

In his defense, he had seven classes this semester thanks to Crowley overloading him with undergrad courses that no one else wanted to teach, namely Humanities I, II, and III. They were basically history classes with some music, popular culture, and politics thrown in. Dean thought those would be his easiest ones, maybe even entertaining. But overall, it was just a lot of fresh-faced freshmen and sophomores who didn’t want to be there anymore than he wanted to teach on the British colony of Roanoke. 

Benny snorted. “You need help.”

Dean rolled his eyes and sat back in his chair. “Like what, a personal assistant? Think it’d fit in the spring budget next to Dick’s espresso machine?” 

His friend gave him a look crossed between amusement and long-suffering.

“You could get a TA,” Benny said. 

“A what?”

“A Teacher’s Aid,” he explained. “A lot of the grad students do it as a Work Study thing. Gives them a little extra income for a job they can do between classes. Despite what ‘Don Crowley’ seems to believe, I think we have a little room left in the History department budget for this school year. I’ll approve it if it means you actually turn in your grade reports on time for once.”

Dean mulled the idea over with interest. Perks of being best friends with the department Chair. He still had some reservations though.

“Eh, I don’t know. Having somebody come in here, getting all up in my business…” He began to root between the stacks, looking for his journal to throw back in his messenger bag. His stomach was rumbling fierce now, and it was time for a break.

Benny chuckled. “You can’t even find your business.”

“Got it!” Dean found his journal behind a half-graded stack of midterm exams and grabbed up his leather shoulder bag on his way out of his seat. “All right, I’ll think about it. Come on, I’m starving. Where’re we going again?”

“Sushi,” Benny reminded him, smiling at Dean’s grimace. “We’re expanding your palette, brother.”

“As long as doesn’t have squid balls, I’m good.”

Benny shook his head as they left the office. He made sure to lower his voice when he replied, “You needa lay off the Japanese porn.”

“Whatever. Where the hell’s Cas?” Dean said. The men stopped at their friend’s office down the hall, but “Dr. Novak” wasn’t in. Benny checked his phone and nodded at the new text he got five minutes ago.

“Looks like he’s waiting for us down in the lobby, probably lurking outside the clinic.”

Dean’s lips twitched at a smirk. “He still have that thing going on with the nurse?”

“Who, Meg? Yeah, apparently,” Benny replied.

Dean grimaced. “Fuckin’ yikes. I’d hate to have her sticking me with a needle.”

Nurse Masters’ impeccable bedside manner was so good it could make students cry—even faculty members.

Benny chuckled. “I think they’d just count it as foreplay.”

After a long lunch and an even longer afternoon of back-to-back classes, Dean closed out his day with his favorite class: World Mythology.

Graduate classes were easier to teach. Older students tended to be more mature overall; they met deadlines better and worked harder, even if it was an elective. But he didn’t want to admit that the brightest spot of these afternoons…was you.

Dean’s eyes found you almost immediately when he walked into the classroom. Not only were you always one of the first ones there, but you liked to sit right at the front, between the center of the classroom and the exit door. You greeted him with a smile, and he couldn’t help but return it, if more reserved.

You were wearing makeup more often, he noticed. Your sweater looked comfortable too, and the color of rust, perfect for fall, scooping just enough to be modest, but enticing. Your legs were crossed, those jeans hugging your hips and thighs. And your nails were still long and red. He remembered when they practically speared through his jacket a couple of days ago, after he ran into you on the subway. 

Actually, you ran into him. He broke your fall on instinct.

“’Sup, guys,” he greeted the rest of the class as they trickled in.

But he couldn’t help picturing your red dress. It had fallen just above the knee (enough for him to imagine his hand running in between).

He remembered what you felt like in his arms, all soft curves and breathless exclamation, your eyes shocked and embarrassed, but still dipping down his chest and to his arms. You’d held onto him just as tight, just as close. And just for one moment, he thought your gaze had fallen to contemplate his mouth—the same way he’d been contemplating yours ever since.

“Okay, how’re we feeling on a Monday?” he asked.

In the silence that followed, he heard proverbial tumbleweeds.

“All right, I get it. I’m almost running on empty myself, not gonna lie. But today we’re finally gonna start on one of my personal favorite segments: folktales.”

Dean connected his laptop to the main screen and played his first PowerPoint slide.

“There’s a lot of nuance here, and the idea of a folktale cuts a wide swath. They span basically every culture, because why?” he posed. “How do these stories live on? In books, like the Brothers’ Grim?” 

He waited for a guess, but again was greeted by a tired silence.

You hesitantly raised your hand when nobody else would. He could always count on you for that. 

“Yes, ma’am,” he said, gesturing at you. 

“Through the oral tradition,” you answered.

“That’s right,” Dean said, though he pointed over at a guy in the back who was already snickering. “Lock it up, Joey. I hear you back there.”

The rest of the class laughed, finally gaining a bit of life from their otherwise end-of-day snoozing. Dean noticed your little smirk. It made a smile tug at his lips too.

He took the opportunity to turn his back to the class, so he could click to the next presentation slide.

“Folktales have been passed down from generation to generation, usually because somebody told somebody else the story,” he continued. “Parents scaring the crap out of their kids with cautionary tales, usually so they don’t get taken or eaten by some mythical monster. Allegories that always end with a moral, like Aesop’s fables. Or tribes telling the important histories of their people. We’re talking legends and myths, demons and tricksters, even star-crossed lovers, and stories of forbidden love…”

As usual, you were one of the only ones taking copious notes. Dean didn’t mean to notice, but he had to figure about five more pages of your notebook were filled by the end of class. 

He finished Part 1 of his lesson with just a few minutes to spare, so he dismissed everyone early at 4:55 p.m. You put away your notebook and pen into your messenger bag and made your way over to the podium, where he was disconnecting his laptop from the TV. A group of girls who sat behind you shot their flirty smiles at him. 

“Bye, Professor Winchester.”

“Bye, ladies. See ya Wednesday,” he said, barely looking up at them. But when he saw you approaching in his peripheral vision, his lips tugged at a smile. He tried to ignore a tremor of something in his gut. “Hey. What can I do for you?”

“I just have a quick question,” you said, but he saw the way you waited for the rest of the class to filter out of the door before you asked it. “Um, first off, I just wanted to say thank you for the other night. You know, walking me home, and kinda…saving me from breaking an ankle on the ice.”

Yeah. Dean remembered it all too well.

Saturday (Three Days Ago)

“It makes sense, since you’re an English major, but your passion always comes through in your essays. I’m really glad you decided to take my class this semester,” he said. For the record, it was genuine.

You demurred further at the praise. “Oh, thank you. It really is my favorite class so far this year, but…that’s because you’re the one teaching it. You’re really good at telling stories. You make them simple and easy to understand, even when we’re talking about hell hounds and old ghost stories, or the uh, Oedipus complex, or something.”

Dean smiled in amusement, but it was his turn to be touched, even if it surprised him too. You were just so honest and free enough to speak your mind. It was refreshing.

“Well, thank you. Glad to hear at least one person’s getting something out of it,” he said, his smile warming for once.

You smiled too, looking at him through your lashes. “All right well, thanks again for walking me home. I’ll, um…see you on Monday-ayy!”

You stepped up onto the first stair leading up to your apartment and caught an icy patch with your red-bottomed heels. A gasp fell from your lips as your arms spun out to catch yourself on anything that could keep you from falling, and that happened to be Dean—specifically his coat, and then his biceps when he moved in fast to keep you upright.

He ended up gathering you into his arms while you clung to his coat. Your red nails bit into the dark fabric. In his mind’s eye, he could imagine them popping the buttons of his dress shirt, carving shaky lines of heat and pleasure across his skin.

Fuck. He bit the inside of his cheek hard to rid himself of that image, his jaw ticking in response. But another one just replaced it when his gaze met yours, half-lidded and shocked, but…contemplating.

Hot breaths mingled in between, puffing visibly on the cold air.

“God, I’m sorry!” you breathed.

“Don’t worry about it.” He cleared his throat past the slight roughness in his voice. “You all right?”

“Yeah. Yeah, um…Take Two,” you said, laughing weakly.

You aimed to let him go and continue on up the stairs by yourself, but Dean couldn’t stop himself from trying to help you. He held your elbow at least, with a hovering hand by your waist in case you slipped again. When you finally made it to the door, you paused and turned to look at him over your shoulder. Again, that look in your eyes said you were debating something in your mind.

“You okay?” he asked again.

You nodded. “Yeah, I just, um…you know what? Never mind. Uh, good night!”

Dean nodded, giving you a casual salute.

Now...

“No problem,” Dean said, clearing his throat. “Just glad you made it home safe.”

You smiled, glancing down at your feet. He had to wonder if you were blushing.

“I did, thanks to you! But I also wanted to ask if the midterms from October were graded yet,” you said.

He blanked on that one. He knew that stack of exams was somewhere on his desk. Now when did he see that—this morning, or last Tuesday?

“Sorry, I’m a little backed up on my grading, but I promise I’ll get those back to you guys soon,” Dean replied, sheepishly rubbing the back of his neck. He could see you were a bit disappointed, but you nodded.

“Okay, no problem. Thanks, Professor.”

At least you were polite about it.

You both left the classroom together, but went your separate ways once reaching the hall. You gave him a little wave as you left. He raised a hand back and wished you a goodnight. All the while, he tried not to let his eyes linger on your lips, or the gentle curves of your body clothed in soft cotton and denim.

He went back to his office, and after the old door creaked open, he took in the piles of crap all over his desk. All over everywhere. Jesus. I have let his place go a bit, huh?

Eventually he found what he was looking for in the bottom-left drawer: eighteen stapled packets of Mythology midterms. 

With a heavy sigh, he dropped the pile on top of his closed laptop and walked just next door to Benny’s office. Dean pushed the door open and caught his friend staring sternly at his screen, like he was trying to decipher the Da Vinci Code. His favorite book, The Golden Age of Piracy, was on his desk. If Dean had to guess, his brain was about to break reading 103 misspellings of Caribbean.

But Benny noticed the presence filling his doorway unannounced and rose a brow.

“I don’t need any Girl Scout cookies, thanks,” he said.

Dean rolled his eyes. “All right, I give.” 

Benny frowned in confusion. “Give what?”

“How do I get a TA?”

You had to take a forty-minute subway train every day just to get to and from the West Village to your apartment in Washington Heights. It wasn’t easy, but both you and your roommate often did it together when your schedules linked up, so it made the trip more bearable.

Today it somehow felt more taxing than usual when you and Charlie practically stumbled into the apartment, drunk on nothing but exhaustion. The lingering smell of weed and piss was probably hauled with you from the terminal. You shed your messenger bag, your keys, your boots—all of it on the dining table with a rather dramatic, "Uuuugggghhh."

“Feel that in my soul,” Charlie agreed, but she was more civilized as she tossed her keys in the little basket on a table by the door. You amended yourself, grabbing your keys to deposit them in the same bucket. You could never get confused with your keys and hers, because she had a collectible keychain of Princess Leia in her brass bikini, holding a blue lightsaber. She always said Leia was gipped of being a Jedi alongside her twin brother.

“I think it’s your turn to cook,” you said.

Charlie met you with a scandalized scoff. “Fat chance, bitch. I cooked three days last week.”

“You made tuna sandwiches!”

“Okay? I still had to crack open the can. I added mayo. I chopped onions. Now that’s love.”

“Honestly could’ve done without the onions,” you said, and threw yourself into a seat on the couch.

“Ungrateful swine,” Charlie muttered, but she sank down next to you and rested her head against your shoulder. It was only Monday, and both of you were too brain-dead to function. You looked over at her, and she picked her head up to look at you.

“Pad Thai?” you both asked, almost in unison. Then you lit up with incredulous smiles.

“Oh my God! We literally share a braincell at this point,” she said.

You giggled. “Hey, I’ll take that. You’re literally the next Steve Jobs, so I’m honored to share even one mighty cell.”

She made a gagging sound. “Ech, please, not that narcissistic ass. I’d rather be the next Grace Hopper. She literally created the first language programming compiler. It translated English language code into computer code.”

“Yeah, totally.” You nodded sagely, like you understood what that meant. You and Charlie both knew the truth, but she appreciated you for matching her energy.

“All right, let’s order. My stomach’s about to eat my liver,” she said, already pulling out her phone to find UberEats.

You sighed. “If we’re going to keep ordering out like this, then I’m gonna need another job.”

“Another job? Are you crazy? You’re already stressed working at the library with a full course load,” Charlie said, even though her thumbs were flying away on the small screen, adding appetizers and dessert you had no business buying.

Or eating, you thought, with a self-deprecating grimace at your thicc thighs. If you were honest, the “freshman 15” had lingered. Now that you were in grad school, you had even less time to work out and more compulsions to stress eat.

“I know, but that’s only part-time, and Marv just told me he has to cut my hours. Something about department budget cuts. Tutoring’s not going to be enough at this point…maybe I can find something else on campus,” you said. 

“Yeah, like another Work Study job,” Charlie suggested. “You know that’s how I got into the IT department. Then they hired me full-time after I graduated.”

You nodded. “That’s not a bad idea. It would be nice to have job security after I graduate next semester too.” 

You would have to check the Career Development page that EU had for students. 

“Okay, you want to split some duck salad on the side, or the spring rolls?” she asked, focusing back on the food. 

You tapped your fingers on your chin in deliberation. “Both? That way we have leftovers for lunch tomorrow.”

“Both. Both is good,” she said with a smile. 

Meanwhile, you dragged yourself up to your feet and went back to the kitchen to grab your laptop. You plopped back down next to Charlie. But when you cracked your laptop open to your email, you saw a new one from Professor Winchester.

Update: I found the midterm exams. Will have them graded by class time on Wednesday...or Friday. Thanks for the reminder. – D.W.

You smiled and typed out a reply.

Awesome. Thank you so much! 

You didn’t even notice that you hummed cheerfully while you navigated over to the school website, looking for the Career Development page.

Charlie clocked your lighter mood (and that email) with a suspicious smile. 

“You know, you’re always more chipper on Mondays, Wednesdays, and Fridays. Could it be because you got to see your favorite professor?” she said knowingly.  

You tried to dim your smile, avoiding her gaze while you figured out the right filter settings for this job search. Newest to Oldest. Part-Time. Work Study. Graduate Student.

“I’m just happy we’re getting food. I’ve had a long day. Adam and Joey were whispering and joking like ass clowns all through the lecture again, so I had to focus all my brain power on taking notes and not hurling my pen at their heads.” 

Charlie rose a brow, her smile speaking volumes. “That’s fair. Man-children suck.”

You snorted. “Yeah, be glad you don’t have to date them.”

Charlie had been seeing Dorothy (she preferred Dee), a hot brunette on the Security team for a few weeks now. She looked petite, but the girl had a noticeable edge that sometimes intimidated you. 

“You don’t either, by the way,” Charlie pointed out. 

“Trust me, I now actively avoid them,” you muttered. The last dude-bro you tried to date cheated on you with some sorority girl while plastered on Ecstasy.

“And I’m very proud of you for that,” Charlie nodded. “But back to Professor Hottie.”

You rolled your eyes, despite your smile. “You think he’s hot?”

“Objectively speaking. I can appreciate a specimen of a man.” And her smile turned sly. “Just so you know though, the guy has a lot of porn stashed on his computer. Like, a lot. He must not have a personal laptop at home.” 

You paused, your eyes going wide. 

“Oh, God. He’s not doing…that at work, is he?” you wondered. 

Charlie contemplated the unsavory thought with a grimace. 

“Couldn’t tell ya. I don’t pretend to understand the inner workings of heterosexual men, but it makes you wonder why he’s backed up on all his grading. Clearly he’s not backed up in other areas.”

“Jesus.” You snorted and laughed with her until your stomach hurt, though you covered your mouth on instinct at the ungainly sound. Your face began to burn with a hot blush at the thought of a man like Professor Winchester…doing some self-care in his office.

Did he do it between classes? After work? Before you saw him in the afternoon? You racked your brain and tried to remember if he ever looked a little too relaxed coming into class. 

Just then, Charlie’s face came in close over your shoulder.

“You’re imagining it, aren’t you?” she teased.

“I’m not,” you said. Your blush was spreading down your neck, all prickly and wrong (and yet, very right).  

Charlie squeezed your shoulders playfully. “What, you wanna give him a little helping hand?”

“I do not!” you yelped. You grabbed a throw pillow and tossed it at her head. 

Charlie laughingly relented. “Okay, if you say so.”

You rolled your eyes and pursed your lips. Instead of goading her on with further denials, you focused again on your laptop screen while she finished ordering dinner. 

You started exploring the university Career Development page, looking for another part-time job on campus that might fit between your classes. The first new entry at the top made your eyes pop wide open.

Teacher’s Assistant – History Department

Reports to: Professor Dean Winchester

AN: I think you see where we're going with this lol. Lots of setup in Part 1, but now you've met most of the key characters! How do you like the return of Professor Winchester? 😉

Next Time:

“Good morning,” you chirped. You held onto the strap of your messenger bag out of habit and a steaming Starbucks coffee in the other. It brought the aroma of cinnamon spice and vanilla into his office.

Your sweater was an earthy green today, your lipstick dark and plummy to match. His eyes subtly swept over you on reflex, noting the long skirt draped around your curvy hips. He wondered what would be softer, the brown suede, or your skin.

Come on, dude. Get it the fuck together.

He nodded, with a more gruff, “Morning,” in reply.

“How’s your day going?” you asked.

“Pretty good. Haven’t had any drop-out casualties yet this week, and most of you guys show up on time. Counting that as a win,” he said, closing his laptop. “What can I do for you?”

Instead of answering, you sucked in a little breath to steel yourself before you set the to-go cup of coffee on his desk, by his hand. Dean peered at it, then back up at you in confusion.

“What, is it my birthday already?” he quipped, but he raised the cup to his face and inhaled the sweet, mouthwatering scents of fall and froth.

“Call it…more of a bribe,” you said. A smaller smile of nervousness and hope tugged at your lips. “I just wanted to let you know that I applied to your job posting for a TA. I know you’ve probably gotten a lot of applicants already, but look! I’m good at coffee runs.”

Dean’s more genuine smile overtook his face. He took a sip of your bribe and had to agree—for Starbucks coffee, it wasn’t half bad. And it was a thoughtful pick-me-up for the mid-morning.

“Uh-huh, keep talking,” he teased, taking another hefty sip.

ᝰ. PART 2 COMING TO TUMBLR/AO3 -> 10/24 (new chapters on Fridays~)

Part 2: For a Charm of Powerful Trouble

On Tuesday morning, Dean announced that he was looking for a Teacher’s Aid at his first graduate level class: Religion, Myth & the Supernatural. By the time he checked his email again at lunch, he was shocked to find over 50 applicants to his job listing in the Career Development board. 

All but three grad students seemed to be young women. He scrolled through them when he got back to his office, but his breath almost stilled when his eyes caught on your name, your profile picture, and your neat and professional-looking resume attached.

No way…

A knock on his door almost made him jolt in his seat. He cleared his throat.

“Come in,” he called out.

The door opened, revealing you on the other side of it with a sunny smile he wasn’t ready for. Dean’s grip tightened on the armrest of his office chair.

“Good morning,” you chirped. You held onto the strap of your messenger bag out of habit and a steaming Starbucks coffee in the other. It brought the aroma of cinnamon spice and vanilla into his office.

Your sweater was an earthy green today, your lipstick dark and plummy to match. His eyes subtly swept over you on reflex, noting the long skirt draped around your curvy hips. He wondered what would be softer, the brown suede, or your skin.

Come on, dude. Get it the fuck together.

He nodded, with a more gruff, “Morning,” in reply.

“How’s your day going?” you asked.

“Pretty good. Haven’t had any drop-out casualties yet this week, and most of you guys show up on time. Counting that as a win,” he said, closing his laptop. “What can I do for you?”

Instead of answering, you sucked in a little breath to steel yourself before you set the to-go cup of coffee on his desk, by his hand. Dean peered at it, then back up at you in confusion.

“What, is it my birthday already?” he quipped, but he raised the cup to his face and inhaled the sweet, mouthwatering scents of fall and froth.

“Call it…more of a bribe,” you said. A look of nervousness and hope tugged at your lips. “I just wanted to let you know that I applied to your job posting for a TA. I know you’ve probably gotten a lot of applicants already, but look! I’m good at coffee runs.”

Dean’s more genuine smile overtook his face. He took a sip of your bribe and had to agree—for Starbucks coffee, it wasn’t half bad. And it was a thoughtful pick-me-up for the mid-morning.

“Uh-huh, keep talking,” he teased, taking another hefty sip.

“You know I’m a hard worker, and I’m really organized, like to the point where my OCD annoys the crap out of my roommate.” You paused, eyes widening, raising up placating hands. “But I mean, of course I’d try not to annoy you. I’m not that bad. She’s just ridiculously messy. Like, do dirty socks belong on top of the coffee table? No. And why did I find half a grilled cheese sandwich on the bathroom counter last week? That’s just unsanitary.”

Dean’s lips twitched. He just listened to you ramble and had to marvel with his chin held in hand, his elbow on the desk. Eventually you realized that your mouth was running faster than your brain, and your lower lip got tugged between your teeth. He wondered how bad you were blushing.

“…Anyway,” you said in embarrassment, “I also work in the library here on campus, so it’s super convenient for both of us. I can pop over here between classes, or later in the afternoon, whatever works best for you! I really need this job so I—”

“All right,” Dean said, trying to temper his smile. His gut clenched with a warning though.

He knew good and damn well this wasn’t a good idea, for reasons he was ashamed to admit. None of them he could say out loud. On the other hand, you were also perfectly qualified for the job. His mind spiraled as he tried to conjure a plausible excuse for turning you down without disappointing you, or hurting you.

He opened his mouth to reply…

“You guys might’ve heard that I’m looking for an assistant,” Dean said, standing in front of a room full of mid-twenty-somethings. Half of them looked bored, the other half a little too glued to his every word. He was used to that being a gender-dependent ratio. 

He’d already made this announcement to rest of his classes today, but yours was the last. He glanced over at you with a hint of a smile.

“Well, my short-lived search has come to an end,” he said. He announced your name and gestured to you where you sat, smiling, a little embarrassed. “She had a strong resume and an even stronger pitch. Thanks for stepping up. I’m sure you’re gonna keep me on track for the rest of the year. Maybe I can even get your tests back to you guys within a month this time.”

That said, he grabbed a stack of midterms from his podium at the front of the classroom and began passing them back. He ignored the looks of disappointment from the girls and focused on finding the right name with the right face. Even more than halfway through the semester, he was still trying to put that together.

“Aw come on, bro,” Joey groaned when he saw his grade.

“Pounding Red Bull and cheese fries isn’t the same as taking notes, dude. Lesson learned,” Dean remarked.

“This one was hella hard though. Half of it was straight up essays,” his friend Adam complained. Somehow Rick and Morty here were getting their master’s—Adam in Film, Joey in Sports Business.

“You know you’re in grad school, right,” you said wryly. Adam shot you an annoyed look. It only got worse when Dean laid your midterm exam on your desk.

“Great job” was written in his hasty scrawl, right below the red A circled at the top.

By the end of class, the other girls either subtly snubbed or fake smiled at you like a pack of Regina Georges. You had apparently become Lindsay Lohan. You were a little uncomfortable with their scrutiny either way, but you couldn’t help but be excited as you walked with Dean out of the classroom.

You’d have to stamp down the butterflies flapping their massive wings in your stomach though. You weren’t in this to fuel some asinine crush, you told yourself.

You just really needed an easy job that could replace the hours you were losing at the library, and you knew Professor Winchester. He was a good teacher, and a good guy. You just needed to keep things respectful and professional, and most of all, not let your mouth runaway with you (again). 

You just forgot about the catastrophe that waited for you in his office. He’d said he could use you right away, and he wasn’t kidding. You took in a steadying breath after he opened up his office to you. How the hell was it already worse than it was this morning?

“I know,” he said, rubbing the back of his neck after spotting the look on your face. “It’s got the whole, ‘organized chaos’ thing going on I guess. But uh, anyway, you can fill out the paperwork and stuff over at HR. I’ll make sure you get paid for the hours you work today.”

You let your eyes adjust to the stacks of paper piled precariously all over his desk, the second desk in the corner, in between books and miscellaneous items on the wall-to-wall shelf behind his desk, and even on the floor in the far corner.

He seemed to be using his filing cabinet as a table. It now held a cracked-open pizza box with half a pepperoni and sausage. You could smell it from here, along with something mustier underneath.

“You hungry?” he said, noticing your gaze on the box.

You blinked and shook your head. “Oh, no it’s okay. I’m just…trying to figure out your system here.”

Dean snorted. “Don’t really got one. I just kinda find room and work from there.”

You nodded slowly. “Uh-huh.”

You truly wondered how the hell he found anything. He slid past you and went to his chair, first depositing his laptop on the only free square on his desk, then dumping his shoulder bag on the floor by his feet.

“I really just need help with the easy tedious stuff, like quizzes and homework for my undergrad classes. There’s a desk over there you can work at,” he said, gesturing haphazardly at the table in the corner covered by computer crap and a leaning tower of cassettes.

“Oh wow,” you said. You went over and peered at the Skid Row cassette on top. “I haven’t seen these since I was a kid.”

Dean nodded. “Yeah, uh, those were my dad’s.”

His tone was a shade deeper, nostalgic. You looked over at him and caught the way he rubbed at his watch. You remembered him mentioning it once in class; another thing his father passed down to him. You saw where his love of classic rock came from.

“You guys must’ve had a lot in common,” you said.

He flickered at a rueful smile. “Not as much as you might think.”

Your head tilted questioningly, but he refocused on what he was going to give you to start working on.

“All right, you can start with these in the top-right corner here. A lot of this crap is old, and I’m tired of looking at it,” he said more gruffly.

Your lips hinted at a smile. “Well, that’s why I’m here! Let’s go.”

You knew you had your work cut out for you here, but you tried to maintain an upbeat attitude while you collected the large stack of tests for Humanities I, careful not to let them spill out of your hands. Your fingers hooked on something by mistake, and you realized it was a Fritos bag, old and open.

I thought there was a weird smell in here. Musty corn chips.

You set down the stack to pick up the bag and ask if he wanted you to throw it away, but to your horror, it started moving.

You yelped and tossed it away from you. Your soul leapt out of your body when a cockroach came scurrying out of the bag and across the floor. 

Dean stomped on it with his boot.

He met you with a sheepish look. “Sorry ‘bout that.”

He slowly raised his boot, revealing the crushed, twitching body with its disgusting crinkled legs. The antennas were still moving.

You gagged, holding the back of your hand to your mouth as you turned your face away.

“Okay,” you said. “First thing’s first, I think maybe we should clean and organize this…space.”

You gestured at his entire desk. Dean was too embarrassed to argue with you. 

“Is there at least some Windex and paper towels somewhere? Disinfectant wipes?” you asked.

“In the teacher’s lounge, probably,” he said. “Here. While you check that out, I’ll…clear off the desk.”

Rubbing his chin as he contemplated how exactly he was going to do that, he gave you his school ID badge so you could get into the faculty lounge. Only faculty and staff had access.

Your hand brushed with his on the handoff. Your gaze dipped down to his long fingers. 

You quickly met his eyes. “Thanks. Be right back.”

Benny almost ran into you when you got out of Dean’s office. You knew him as Dr. Lafitte. You also knew that he and Dean were friends. Your face flared with a blush on reflex as you stepped back.

“Sorry!”

“Everything okay?” he asked. “Thought I heard something.”

“Oh, my bad, that was me. Professor Winchester may or may not have a…bug problem,” you said.

Benny raised a brow. “Really?”

Your smile was more like a grimace. “Not to worry. I’m coming back with cleaning supplies.”

Benny nodded in agreement as he watched you go down the hall. He shook his head and went into his friend’s office. Looks like he found his TA.

Meanwhile, you continued on to the Faculty Lounge. It was mostly just a kitchenette, a couple of round tables, and a printer on the other side of the room. You were surprised to find Dick Roman collecting some papers from the feeder.

“Oh, hi, Dr. Roman,” you greeted.

He gave you a cursory nod, though he rose a curious brow.

“I’m surprised to see you out of the Vaught Building,” you said.

The main building that made up the Business School had been funded by Edward Vaught. His grandson, Nick, had been the Dean of Business up until he retired last year. You thought the age of 42 was a bit early to retire, but what did you know about the inner workings of Old Money? The Vaughts were practically synonymous with Rockefeller and Vanderbilt, Astor and Carnegie.

“Our printer is being replaced, so I had to come over here to make copies,” Dick said. It was financial data he didn’t trust in anyone else’s hands, not even his assistant.

“Gotcha,” you nodded. “Do you happen to know where the cleaning supplies are?”

“Down there.” He pointed to the lower kitchenette cabinets beneath the sink. You crouched down and peered inside, finding more trash bags and latex gloves than anything else.

“Huh, not seeing what I’m looking for here,” you muttered to yourself.

You didn’t realize the man’s blue-eyed stare was half amused, half lingering on your ass when you got down on your knees on the linoleum to get a better look.

“It could be deeper in the back,” he said.

You struggled to duck your head and arm further in, unintentionally giving him a better viewing angle. Your sweater began to ride up as well, flashing a small strip of your lower back. 

Dick tilted his head, still amused.

You pulled out a white box in confusion, coughing when a small puff of powder escaped.

“Borax? Who the hell uses this?” you wondered.

You set that aside and kept digging. Eventually you found success with a blue bottle of Windex, a can of Lysol, and a pack of lemon Pledge wipes. You were going to disinfect that entire office before the end of the day.

You huffed a bit while getting off your knees and back onto your feet. 

“Okay, now I need paper towels.” 

“Check the top cabinet, if you can reach,” Dick advised.

You soon realized that you couldn’t, even when you rose up on the tips of your toes. Dick stepped up behind you. He was nearly as tall as Dean, at least six feet. He was just leaner, less broad. He opened the cabinet, grabbing a roll of paper towel for you. 

“Thanks so much,” you said. 

Dick smiled politely and asked your name. “I don’t think I’ve ever seen a student manage to get back here.”

You paused, realizing he must be wondering how you got in.

“Oh yeah, I’m a grad student, but I’m Professor Winchester’s new TA. I just started today.” 

Something shifted behind Dick’s eyes, maybe interest. His smile returned.

“I see. You’ll probably be a great help to him.”

“Well, I’ll do my best,” you said with a laugh. 

You wore genuine modesty well, he noticed. It wasn’t something he came across very often. 

“I’m sure you will,” he said. “I have to get back to my office, but you have a good day.”

You nodded, offering him a polite smile.

“Thanks, you too.”

Back in Dean’s office, Benny shook his head while the man himself used a napkin stained with pizza grease to peel the dead roach off the carpet.

“Why’d you give her your badge?” Benny asked.

“Why do you think? She’s going to the lounge to find some stuff, about to help me do some early spring cleaning,” Dean said, looking around. “I guess I’ve let it go a bit too long.”

Benny snorted. “Well, you’re sure making use of your TA already. You made a good choice. I know her. She was in my Humanities classes when she was in undergrad. Good kid. You can tell she gives a shit about her grades, her career.”

“All right, she’s not a kid,” Dean said. “She’s a…respectable young lady.”

Benny’s head tilted as he studied that hesitation. He thought he read something between those lines. 

“And does this respectable young lady happen to be one of your students?” he asked.

“Yeah, she’s an English major, but she’s really into Mythology. Real, uh, bright.”

“Uh-huh. And nice to look at,” Benny said, raising a pointed brow. 

Dean shot him an affronted look. “Well, clearly I can’t speak for you, but I’m a professional, okay? I don’t, uh, see her like that.”

Benny’s gaze was shrewd. “Just…be careful, brother.”

Dean frowned. “Hey, what do you think I am, huh? Some kind of knuckle-dragging—”

The door pushed open, and Dean cut off his own words. You came in with cleaning supplies gathered in your arms and a determined glint in your eye.

“Okay, I got the stuff. I even found some plastic gloves.” You showed him and Benny, but mostly Dean, your haul. “We can even get that stain under your laptop.”

Benny chuckled and waved a hand. “Well, have fun with that.”

“Oh, I will,” you said, aiming a salute his way.

Benny smiled and ducked out of the office, but he shared one last look with Dean that had a hidden edge of warning. Dean nearly rolled his eyes. He blinked and moved out of the way for you though. You placed your supplies on the corner of his now clear desk, and you slipped on a pair of your procured gloves. 

“You know you don’t have to do all that,” he said, scratching the back of his neck.

“It’s okay, I want to,” you said. You weren’t even looking at him. You were staring at the stain, the layer of dust across his shelves, the mess. “I just…it bothers me.”

Dean huffed a laugh. “All right. Let’s do this then.” 

He grabbed a stack of gradebooks off his desk, giving you another corner to wipe down. 

The two of you spent the next couple of hours cleaning and reorganizing his office. Already you were turning his work life upside down, but he could admit that in this case, it was for the better.

Not only was his entire desk clear, the dark mahogany wood polished and smelling like lemon Pledge, he now actually had room for that extra monitor previously sitting on your desk. It was now connected his laptop and gave him a bigger screen to work off of. You even helped him set it up, as well as find a stapler, a pen holder, and a coaster for his favorite coffee mug.

Your desk then became a starting point for everything that needed to be graded. The many stacks of quizzes, tests, homework assignments, and even essays were all clipped together and arranged by class and date, oldest to newest.

By the time Dean walked out with you to the parking lot, it was nearly 7:00 p.m. It was getting dark enough that he felt justified in walking you to the subway, making sure to thank you for your help and dedication. You just gave him one of those bright smiles and waved him off.

“See you tomorrow,” you said, hopping onto your train.

Dean nodded. He would see you tomorrow, he realized. You’d agreed to come over to his office every weekday, Monday through Friday at 5:00 p.m., after his last class of the day. Three out five of those days just happened to be your Mythology class. There literally wouldn’t be a day of work where he didn’t see you.

The thought almost brought a smile to his face, before he realized how unbelievably screwed that made him.

A text from his brother reminded him why he was taking a different subway train today. The F train took him from the West Village up and over to Lexington Ave, where he met up with Sam and his wife Eileen for dinner at some new Latin spot they wanted to try. According to Eileen, the arepas were supposed to be authentic. She used to vacation in Colombia with her family when she was a kid, winters in Aspen, summers in Europe.

Dean ate half his weight in fried pork, rice, and beans while Sam updated him on one of his cases. He was a lawyer on EU’s Legal team, and apparently Zachariah had beef with someone who kept switching his highly coveted faculty parking space sign right in front of the main building with one of the guest spaces, all the way out near the football field.

“That’s what, like a ten-minute walk?” Dean said. “Inconvenient, but not something to sue somebody over.”

“In Italian loafers?” Eileen pointed out, smiling mischievously.

Dean smirked. Yeah, he could picture Zach hoofing it in his Armani suit and polished leather shoes.

“The guy’s so worked up about it that he’s claiming harassment,” Sam said.

“Got any suspects, Prosector?” Dean asked, taking another mini beef empanada from the appetizer basket between them.

“Zach’s pointing the finger at Raphael, but I’m thinking it’s Gabe.”

Dean chuckled. “Gabe, huh?”

That was the Film professor who had a habit of letting his students run wild with their cameras. It had gotten him in trouble when one of them snuck into one of the women’s bathrooms and caught a frame of Miss Butters’ undercarriage. Crowley’s poor assistant practically had a heart attack before she beat the sophomore with her purse. Dean called that one just deserts.

“You know what, I believe it,” he nodded. “The guy’s shifty. I still think he’s the one who gave the football team the idea to moon Crowley at that pep rally last year. He was the one filming the whole thing.”

The look on Crowley’s face though? Fucking priceless.

“Exactly,” Sam nodded. “So stay tuned on that one.”

“Cas is still dating the school nurse, right?” Eileen asked. She signed the word for dating.

She had lost her hearing as a baby, but she said it had actually helped her in her career as an artist. It allowed her to literally tune out the world and stay focused on whatever medium she was working with, be it clay or canvas. She’d also helped Sam become fluent in ASL. Dean was working on it too.

He nodded and signed back, Think so.

Her father, Patrick Leahy, was also the President of Edlund University. Compared to its competition, NYU, theirs was a smaller private school. But still, serious money. Sam definitely married above his paygrade. Not because his wife had a trust fund, but because she was more genuine and down to earth than a lot of the faculty Dean worked with—Zach included.

That didn’t mean she wanted to skimp out on the tea though.

“Yeah, they think they’re being slick with HR,” Sam chuckled. “But at least Cas’s getting out there, you know.”

He shared a look with his wife, then eyed his brother next, in a way that almost had Dean rolling his eyes. He steeled himself in preparation for what he knew was coming.

“You know, Eileen has a friend,” Sam said.

“I’m sure she does. She’s a cool chick,” Dean said, chomping on another empanada.

“Her name’s Lisa. She’s super chill, smart, brunette, a yoga instructor. She owns her own studio,” Sam said, listing her many accolades.

Dean’s brows rose. “Yoga instructor?”

Sam smiled. “Had a feeling that would grab your attention.”

Dean did roll his eyes this time. “Since when do I need help getting a date, huh?”

“You don’t, but from what I hear, you’ve stopped trying,” Sam said pointedly. 

Dean let out a heavy breath through his nose, ran a hand messily through his hair. His brother must’ve been talking to Benny and Cas behind his back. 

Dean shrugged. “What do you want from me, huh? I’ve got too much going on at work to add anything else.”

The latest being taking you on as his assistant. For some reason, he was reluctant to bring up that tidbit of news.

“It’s just easier to keep things casual,” he said.

Sam shook his head. “That’s what you’ve been saying for the past eight years.”

Eileen sent her husband a slightly warning look. She caught the way Dean’s jaw ticked, his green eyes flatting with more than just annoyance. 

“Right,” he said.

“Dean, I just mean…it’s been a while since Cassie. Don’t you think it’s time to move on?” Sam said.

An uncomfortable stillness settled across the table. Dean wiped his mouth with a napkin and flagged down their server.

“Hey, man. Can I get another whiskey, neat?”

With that, Eileen wisely changed the subject, asking Dean what kind of pies he wanted for Thanksgiving this year. 

Regardless, the damage was done. He knew Sam meant well, but nothing ruined his appetite more than talking about the only woman he ever tried to live with.

The woman who said yes, a year after they met.

The woman he’d actually seen forever with.

The woman who left him three months later, and never looked back.

AN: Nothing like closing out with a hint of heartbreak. 😅 But the ball's now rolling with reader and Dean. The question is, how long can Dean keep it together? 😂

Next Time:

His first real test came on Thursday. You were already at your desk with a batch of quizzes. It was multiple choice and he gave you an answer key, so you were making quick work of it. Dean kept his office door open, both as a courtesy to you, and…more of a safety precaution for him.

But that allowed hallway distractions to venture in, like Adam Milligan and his friends yapping and laughing, their voices rebounding off the walls. You eyed the hallway in annoyance when they only got louder. They were bouncing what sounded like a basketball between each other. They weren’t even on the basketball team.

Dean sighed roughly and got up from his desk. He stepped out into the hall and fixed his eyes on the one guy he recognized.

“Milligan! Take it outside. This ain’t the half-court,” he snapped.

Adam’s laughter died in an instant. The tone of Dean’s voice was enough to have him slapping his friend’s shoulder and lead the rest of them toward the stairwell. Shaking his head, Dean turned back inside his office.

“It might be easier if we close the door,” you suggested.

Dean paused, blinking and pointing a bit hesitantly at said door. “Oh. I was just keeping it open because…you know. Male teacher, female student.”

“I know,” you smiled. “I don’t mind though. I’ll focus better with less distractions.” 

Yeah, me too. That’s why I had the damn door open, Dean thought. But he quirked his head and complied, shutting the door behind him.