03 | Then and Now

"WEAR THAT ON YOUR FIRST DAY THERE and I bet it'll take less than twenty-four hours for him to ask you out," Meredith said, wearing a playful glint in her eyes as she looked at Jen's reflection.

A scarlet flame rose to her cheeks as she did one last tiny twirl in the mirror.

"It'll be too cold," she retorted simply, quickly reeling her friend back to Earth rather than allow herself to get her hopes up. "And he doesn't even know I exist."

Dean Holloway was handsome, popular, athletic, and definitely not into nerdy girls like Jen. Nor would they ever work out—he was a year older than her, so he would be moving onto bigger and better things than college in just a few short months. But her heart apparently hated her and chose to ignore all of these facts in favor of having a massive crush on him for two semesters now.

And ever since Meredith got wind of the fact that Jen and Dean were going on the same study abroad trip this semester, she hadn't been able to keep her mouth shut about all the imaginary scenarios that could kickstart their whirlwind Italian romance. On most days, Jen was in the mood to indulge her and allow herself to daydream about actually falling in love with him. But now that their flight to Rome was a mere thirty-six hours away, she needed to shut down anything that was going to lead to disappointment when the inevitable nothing between them occurred. She couldn't let the opportunity of a lifetime be tainted by something as fickle as a boy.

"Besides, I'm not going across the world to find a boyfriend," she added resolutely as she sat back down on the edge of the bed and smoothed her dress out. "I'm going to learn, remember?"

Never before had such an exciting opportunity directly related to her studies presented itself. The focus of their coursework abroad was to learn about the latest technological advances in Europe. It took what felt like thousands of hours to convince her parents to let her go, but they finally caved in to her argument that it was well worth the minimal price difference compared to her regular tuition.

The girls were interrupted by a loud, rapid knock on the door.

"Who is it?" Meredith called, her lips curving into the beginnings of an irritated frown as the abrasive sound rattled at their ears.

"Is Jennifer in there?"

Jen froze. Meredith's eyes were the size of dinner plates as she turned to her and silently mouthed, What's he doing here?!

She didn't know. The voice was unmistakably none other than Dean's, but they had never exchanged more than a couple of words with each other. What was he doing here? Since when did he even know who she was, much less want to talk to her on a weekend?

"Yeah," she squeaked back as the tempo of her heart increased.

The door cracked open. As if him showing up here wasn't enough to surprise her, she was startled to see that he looked...not good. Pale and wary and not at all like his usual self.

"Hey, could I, um, talk to you outside," he said quietly, but unless Jen's ears were playing tricks on here, there was a tinge of urgency behind his words.

Her throat felt dry as she said, "Sure," and climbed off the bed.

In her attempt to look nonchalant – she most definitely could not let Dean know that just the sight of him was enough to send a swarm of butterflies scattering throughout her stomach – she fought the impulse to glance back towards Meredith. Instead, she simply stepped out into the hall and carefully closed the door. The old hinges creaked like they might give out at any minute.

Dean was exactly the type of boy your parents wanted you to stay away from, the type that Jen was simultaneously both suspicious of and exhilarated by. At school, he was the star student, the teachers' pet, yet she'd heard that he became quite the rule-breaker on the weekends. He rode a motorcycle and snuck onto the roof of the dorm to drink alcohol and smoke cigarettes unnoticed but also volunteered at the homeless shelter twice a month. He was both angel and devil, Jekyll and Hyde. The type of boy who looked at you with sweet green eyes and promised that he'd never hurt you but could never convince you of that entirely. The type of boy who might tear through your life like a tornado and then leave you in the dust if you let him get close enough.

It never crossed Jen's mind that she might be the girl that happened to. She was smart enough, strong enough, cautious enough. And it wasn't enough. Dean might have done nothing, but he was about to do everything. Though he was just a messenger, the blow he was about to deliver was one she might never pick herself back up from.

The first thing she noticed now that she was seeing him more clearly was that he was wearing his school ID strung on a lanyard around his neck, which meant that he was on front desk duty. That wasn't confusing in itself – the RAs of each dorm had to rotate shifts at the desk – but why had he come to talk to her while he was supposed to be working?

Even more confounding was the fact that he swiftly strode towards the exterior doors without another word to her. She hastened to keep up with him.

"...Is everything alright?" she questioned as she caught up with him.

He wouldn't look directly at her, nervously wringing his hands. "So, um-"

Her eyebrows furrowed. So, um? What was so, um supposed to mean? Before she could open her mouth to speak again, they got to the doors and he pushed them open. Their breaths collided with the January air in puffs of mist as he finally came to a halt on the front steps of the dorm. Goosebumps shot up Jen's arms and legs. The thin material of her dress wasn't nearly enough to ward off the cold—she bought it with the intent of wearing it in Italy in the spring, but she'd never get to.

Dean looked uncomfortable as he finally faced her, his eyes wide and lips anxiously pressed into a thin line. "I'm sorry, I know we don't know each other that well, but-"

"But what?"

"The front desk, we just- we got a call from the hospital. There's been an accident and it's...it's your mom. I need to take you there right now."

"Will you take these to Nora when you're done?"

Jen nodded to Elliot and assured him that she would, but her mood withered as she stared at the ever-growing pile of papers on her desk that had just doubled in size from the stack of forms that he plopped onto it. Sorting through these without falling behind on anything else was going to be a trick. He retreated to his office, leaving her alone with her work until she heard the sound of the front door swinging open just a moment later.

When her eyes landed on him, Jen had to stifle a giggle that bubbled up in her lungs and nearly spilled out. Robert Caruso looked almost perfectly prim and proper today—there wasn't a single wrinkle to be seen in his dress shirt, his belongings were neatly tucked into a messenger bag, and his hair was tidy except for one singular, pesky curl that apparently didn't want to stay down.

"You've got a little..." she motioned to touch the top of her own hair as he came over to her desk, hoping he'd grasp what she was getting at.

"Ah, thanks," he said, sounding almost embarrassed but not quite, like he felt he should be but didn't take himself seriously enough for that. He reached to fix it in an effortless manner that told her that this was a fairly regular occurrence. "It doesn't really like to behave."

His eyes floated to the mountain of papers before she could reply to him – not that she would have known what to say. "Any of these interesting?"

"Um, if you think field trip permission slips are interesting..." she offered, hating to sound bored with her job but knowing full well that it would be immensely obvious that she was lying if she attempted to sound thrilled by such a mundane task.

But would anyone find this interesting? she wondered in an attempt to make herself feel less guilty for her lackluster attitude. Satisfying, perhaps. There was undoubtedly a satisfaction that came with organizing. But interesting?

Mr. Caruso came across as the sort who felt that one should be wholly invested in their job, but he didn't deride her for her lukewarm response. Instead, he reached for a stray sheet of loose paper off the desk, plucked a pen out of his pocket, and started scrawling something.

"...What are you doing?" Jen asked blankly, but she took care to make her bluntness a little smoother around the edges by softening her voice.

"Writing an interesting one."

For some reason, that carried a flush of warmth to her cheeks, but her confusion clouded her from questioning it at the moment. "Okay..." she drifted off. "Did you need anything from me?"

"Hmm?" he looked up from the paper and back to her, his nimble fingers coming to a stop. The manner in which he wrote, she noticed, was oddly graceful, but she supposed one learned to write rather quickly when so much of their time was spent grading papers. "No, not particularly. But it's good to see that Principal Ambrose didn't give you a meltdown on your first day."

Jen's curiosity was piqued. "Is she known for being strict?" she prodded cautiously, not wanting to sound too curious.

He shrugged as his eyes returned to the paper. "She's nice, don't get me wrong. She can just be a little overbearing with newcomers. She likes things done her way, I guess..." Now he was the one who sounded curious. "Was she not that way with you?"

Jen shook her head, suddenly feeling like this conversation was drawing too much unwanted attention to herself. "No, I didn't see her much yesterday," she admitted.

"Huh." He sounded genuinely surprised. Then again, Jen knew for certain that Nora was indeed the bossy type, but she'd been so relieved by her willingness to mostly leave her alone that she hadn't questioned it until now. "She must trust you."

Jen nearly laughed, words she didn't truly mean to say out loud accidentally slipping from her lips. "I kind of doubt that."

He raised his eyebrows. "Why?"

She only then realized that she'd dug herself into a hole. "I don't have a lot of secretary experience," she lied, but she'd learned not to lie too quickly. That made it ever so obvious.

He appeared to buy into it, which made her feel a little guilty. "What'd you do before this?"

Not enough, was her immediate thought, but what she said out loud was simply, "My degree is in computer science."

His eyebrows shot up in a surprise that would have irked her much more were it not for the respect that she could see accompanying it.

"Impressive."

Jen pressed her lips together and braced herself for the implied for a girl that always followed that sentiment, whether explicitly or implicitly – in a change of tone, in the subtle flicker of a pair of eyes up and down her body as a man studied her in a new light – but it never seemed to arrive.

Instead, he said, "I don't think I could do that." Then, looking at her with a little more intrigue now, added, "What did St. Catherine's have to do to get a mind like yours?"

Jen would have retorted brusquely had he been looking at her in that clinical way which she detested – as if giving girls an education was just some sort of lab experiment that allowed men to see what they could do – but despite her cynical nature, she couldn't help but believe that his interest was innocent. There was something about him, though she couldn't put a finger on what it was, that made her trust that he had good intentions.

Still, she was a bit baffled by his question. Give me a paycheck? she thought. It was hardly like employers were fighting over her, but she supposed he didn't need to know that.

She rested her chin on her elbow, not at all sure what to make of him. "What makes you think you know so much about my mind, Mr. Caruso?"

His lips curved into a soft smile at her banter, the kind of banter she didn't realize she ever made until it sprung out of her. There was something refreshing about the sensation, like a reminder that she felt normal emotions as humans should. "I don't. But I can tell you're smart."

"How's that?"

He set his pen down and leaned forward slightly. "The smart ones are always the most stubborn."

Jen let out a small huff, crossing her arms. "Who says I'm stubborn?"

He looked amused. "Someone who isn't stubborn would probably just admit they're lost instead of saying they misplaced the copier room," he pointed out.

She didn't immediately have a great comeback for that, so she watched in silence as she finished his note – she really couldn't help but wonder what he was writing – and set it on top of the other papers.

"I'll make sure to come more caffeinated next time if I should always expect a game of Twenty Questions first thing in the morning," she told him, changing the subject rather than admitting he was right.

He grinned. It was a teasing smile – or, as teasing as you could get away with while talking to a stranger at work – but she detected just a pinch of genuine sympathy behind it. "Not a morning person, huh?"

"Is anyone a morning person?"

"We're rare, but we exist."

"Well, Mr. Morning Person-" her eyes darted to the clock on the wall. "You're about to be late for your first class."

That sent him on his way and she was itching to grab his note and read it the very second he was gone, but she forced herself to set it aside for the time being. This paperwork wasn't going to get done on its own.

Around her lunch time, just as she was thinking that she ought to find the time to go say hi to Jude, he beat her to it. She saw a flash of ginger hair out of the corner of her eye and looked up to see him coming over. His arms were full of books, as they often were.

"You get started on that yet?" he asked, eyeing the art history book that was sitting at the corner of her desk, untouched.

"Does looking at the title page count as starting it?" Jen offered. "No, I was pretty tired from my first day. I went and saw your sister, though."

"I was wondering if you thought any of these would be interesting for book club," he explained, evidently referring to the books in his hands. "And I figured it'd be good to see how you were doing. I know Nora can be a little intimidating."

You wouldn't be the first person to tell me that today, she thought, but she didn't say it out loud.

"Pretty well," she assured him instead while her eyes skimmed over the titles. "I don't want to endure The Sun Also Rises again. They just whine about their lives for the entire book."

"There's more to it than that," Jude argued.

Jen wrinkled her nose. "Maybe, but does it matter if it's all kinda boring?"

"It's a classic."

"A boring classic."

He looked like he wanted to protest, but Jude knew better than to incur her annoyance, so he gave up. Jen's eyes, for the first time since she set it aside this morning, floated back to the unread note. "Do you know Robert?"

Jude showed no obvious signs of recognition. "There are probably ten people in this school named Robert," he pointed out. "You're going to have to be more specific than that."

"Caruso," she clarified.

"The history teacher?"

Jen nodded.

"Not really," he answered but leaned forward slightly like he was now curious as to why she'd take interest in him. It wasn't exactly like Jude knew her to be a social butterfly. "Why?"

She shrugged again. "He was talking to me. I was just curious what people around here think of him."

"Well, it's not like I've ever seen him outside of work or anything," he said. "As far as I can tell, he's kind of a mystery. Busy, you know. I imagine it takes a lot of time to do lesson plans for three different subjects. But he must be pretty good at his job, 'cause the students seem to like him and he gets them interested enough to voluntarily check out history books, so it makes my job easier."

Jen just nodded again. That all seemed to line up with the few observations she'd made of him thus far – that he was smart and nice, or at least nice enough.

Jude had to get back to work, but perhaps that was for the best—she didn't really want to give him another chance to argue for the merits of The Sun Also Rises. She, however, had a few more minutes to kill and found herself reaching for the note that Robert had left for her.

His handwriting was messy, messier than she would have guessed from watching the smooth way in which his hand moved – was it a requirement for men to have awful handwriting? – but it was legible.

Dear Jen/Jenny/Not Jennifer,

It turns out that writing and talking at the same time is quite difficult. I regretfully admit that it was bold of me to promise that this would be interesting, so I imagine you have the right to make fun of me for it later if you so choose.

I have a sneaking suspicion you'd like that – I saw that laugh you were holding back when I came in.

But I imagine I owe you one for pointing that out before my students saw me. If you haven't figured it out already, high schoolers can be ruthless. Then again, maybe their parents are even worse and you got the short end of the stick here. Who knows. But if that's true, don't let anything they say get to your head. People who are mean just want to make you feel small.

Look at me getting all philosophical. Maybe this was interesting after all.

Robert

(I'm not sure why I just signed this when you're watching me write it...have a good second day, Jen)

Jen, without giving it too much thought, grabbed a blank sheet of paper off the same stack he'd pulled from. Her fingers were already gripping the pen and quickly gliding across the page before she started to question why she was doing it.

Dear Robert (Mr. Caruso? What are we supposed to call each other around here?),

I applaud your multitasking skills and concede that maybe you're a little bit interesting or at least nice.

Don't let it get to your head.

How long have you been teaching here? You asked what St. Catherine's did to get me as if you aren't the one who's an expert on three different subjects, so I feel like I really ought to be the one asking that question. My own answer is rather simple. I didn't like my last job, so I left. This was a convenient option for the time being, so here I am.

Your turn.

Jen

It didn't strike her until she was already setting her pen down that she didn't even know if she would see him again at the end of the day or not. She had no clue if he usually exited through the same doors he entered or if he supervised any of the clubs that met after school (he did seem nerdy enough that he would play chess or something). But she simply set her note off to the side and turned back to her work, knowing that he would have to show up eventually, even if it wasn't today.

He did, in fact, make a reappearance, but it was later in the afternoon than she would have expected. It wasn't until the school day had been over for almost an hour and Jen was packing her belongings into her bag that he emerged from the hallway and came near her desk to drop some papers in the recycling bin.

"Late day?" she asked.

As he nodded, she noticed that he did not seem particularly bothered by the fact that he was leaving this late. "I was tutoring a student for Italian," he explained. "He really seems to be getting the hang of it now, though."

She caught that small excited spark in his eyes and in his voice, an instant indicator that he loved what he was doing. You could tell what someone's passions were from watching them talk, from watching the way their expression brightened when that thing that set their heart ablaze was brought up.

And she envied him. It made her almost sad for a second, but the feeling quickly simmered away.

"You'll have to teach me a phrase or two sometime," she said kindly, albeit a bit awkwardly.

She tucked the last of her things into her bag, double-checked that her desk was in order, and stood up, passing him her note as she came around to the front of her desk.

Jen hadn't had any intention of walking out with Robert Caruso, but she found herself alongside him nonetheless as they headed to the doors at the same time. He politely held it open for her, their breaths forming little puffs in the winter air as they stepped into the cold.

And she suddenly wasn't at all sure what to do with her feet. She certainly didn't want to hold him up and think he had to carry a conversation with her as they made their way down the sidewalk, but purposely speeding up or falling behind him felt awfully rude. She jammed her hands in her pockets and glanced at the ground, nervous out of nowhere that there was such a thing as walking too fast or too slow. What had gotten into her today?

"Are you a letter person?" he asked, turning his head just slightly towards her.

She felt herself frown a little bit. "What do you mean?"

"I just wasn't expecting a response," he clarified, not unkindly. "It made me wonder if writing to people is something you like to do, that's all."

A very odd feeling settled in her stomach as she watched him tuck the paper into his shirt pocket rather delicately, like he was trying not to wrinkle it too much.

A rush of pink found its way to her cheeks. "Ah, no. Not usually. It just...seemed like the obvious thing to do."

It was obvious, right? She told herself that surely a letter was meant to be replied to, that there was really no use in overthinking her actions.

But now that he had pointed it out, she had no idea why she felt compelled to write back to something that he gave simply to entertain her or why she felt this peculiar sensation thrumming through her veins as he looked at her with warm eyes and a kind smile and told her goodbye.

She didn't know what it was or what it meant, but she was able to banish it once she had watched his silhouette disappear down the sidewalk and she was alone yet again, just herself and the bleak January sky.

Until she got to work the next morning and spotted a folded piece of paper on her desk.

____________________

A/N:

There are occasionally going to be short letter interludes between chapters and the first one is right after this, so make sure to keep reading!

Also, I apologize in advance for the fact that I'm terrible at writing these letters.