Monica stood in front of the mirror mounted on the inside of their closet door, her eyes scanning the reflection as she studied her outfit. Her jeans hugged her tightly around her waist, and the cold, autumn weather forced her to wear an olive green bomber jacket over her black shirt. It wasn't the most glamorous outfit she'd ever worn, but it was balanced and casual enough to be believable, yet cute enough to feel like she cared. None of the glossy magazines she devoured weekly had a section on what to wear to a first fake date with a fake boyfriend. Not that she was surprised. Nervously, she tucked her hair behind her ear and stepped out, catching her roommate's attention. "What do you think?"

Her roommate looked up from the textbook on her desk. Her gaze flicked over Monica's outfit, and she gave a deliberate shrug. "I think…you're overthinking it."

Monica's shoulders slumped at the unhelpful comment before she went back to the mirror. "You're so not helpful."

"And you're not being rational," Georgia replied, not looking up this time as her highlighter dragged across a page. "You look great. Honestly. But this isn't a real date."

"Of course it matters. He's doing me a favor. The least I can do is make it easy for him to fake it. If I look like a mess, it won't help anyone believe we're dating." Monica turned back to the mirror, fidgeting with the cuffs of her jacket. She held her hair in a ponytail to see if that was the route she was taking. Ultimately, she decided it wasn't and let go, letting her hair fall back down.

Georgia rolled her eyes, her voice dry. "Don't let him use that against you all week. A favor is a favor, not a blank check."

She chuckled at her roommates' protective nature. Georgia could be blunt, but there was a solid kind of wisdom in her words, grounded and steady. Still, Monica wasn't worried. She trusted herself, and more importantly, she trusted her older brother to keep Chandler in check. Dressing up a little didn't count as some kind of debt. It was part of the performance. If they were going to sell the illusion, they had to look the part. That included looking cute for dates.

After one last look, she decided that she was ready. Monica put a turquoise scrunchie on her wrist and put her slim purse strap on her shoulder.

"I'll be back in a few hours," she said as she turned toward the door.

"Do you have an emergency change for the phone? Metro card?" Georgia asked, not lifting her eyes this time.

Monica smiled and patted her purse with confidence, "Check and check! I have my wallet and keys in here, too."

Once she was satisfied, Georgia nodded and said her goodbyes to continue studying. Monica went downstairs to the first floor and headed out towards the subway station. The train ride was a blur of soft announcements muffled by static and the chatter of other people. Monica leaned her head on the window, staring out at the dark tunnels flashing past. The closer she got to the restaurant, the tighter her stomach twisted. It's not real, she reminded herself. This wasn't a date, not really. Just a harmless lie for her parents' benefit. Still, she remembered Chandler's voice, warm and slightly husky. She started to imagine what he could look like, tall, maybe, with kind eyes. Her imagination often got the better of her. Whether they liked each other or not, it didn't matter. That thought was reassuring enough to calm her anxieties at least a little bit.

When the subway reached her stop, she followed the crowd out of the station and walked a few blocks to the restaurant. Monica chewed her lip as her eyes scanned the restaurant. It had warm lighting and tall windows, a soft clatter of dishes and laughter drifting out every time someone opened the door. Monica walked in, biting her lip as her eyes scanned the restaurant. Most of the tables were occupied by young couples leaning in close, families laughing, and toddlers giggling as they enjoyed their lunch. She realized she had no idea what Chandler looked like or what to look out for. No photos, no description, nothing. Ross hadn't even bothered to prepare her for that much.

Just as she was about to step toward the hostess, a tap on her shoulder made her startle. Monica spun around to the taller man behind her. His eyes drew her in with the shade of bright blue. They were framed by thick lashes and crinkled slightly at the corners as he gave her a sheepish smile. His brown hair was styled poorly in a 'flock of seagulls' haircut, but he had soft features that made his smile warm and inviting.

"Monica?" His voice was soft and warm, just like on the phone. "Sorry, I didn't mean to scare you…"

Chandler's eyes moved down and then back up, taking her in as her anxiety returned to her stomach. He tilted his head slightly as if trying to recall something in his mind."Wow, you look… different than how Ross described you."

"Different?" Monica's eyebrows furrowed slightly, wondering what her brother had said.

Her question seemed to make Chandler panic, and he tripped over his own words. "I-I mean not differentbad. Different in a way I wasn't expecting… not that I was expecting you to be ugly because you're not! It's just that Ross said you never had a boyfriend because you were a dork in high school, but you look beautiful- I meant pretty- you look nice."

Monica watched him struggle and covered her mouth to hide her laughter. "Thanks…should we get a table?"

"Right! Yes, yes, table!" Chandler turned toward the hostess with a snap of urgency, clearly relieved to move past his verbal trainwreck. He requested a booth for two, and they followed the hostess past rows of tables until they were led to a cozy corner booth tucked against a window.

Once they had settled in their seats across from each other, He was scanning the menu now, brows furrowed in concentration, but Monica couldn't stop herself from studying him again. She hadn't known what to expect, but it wasn't this. There was a boyish charm about Chandler that softened the awkwardness. The bright color of his eyes was a nice contrast with his brown hair, which she would be insisting on fixing later in that ugly style that didn't suit him.

"I think I'm getting the classic cheeseburger and a chocolate milkshake," Chandler said suddenly, pulling Monica out of her daze.

She blinked and looked down quickly at her menu, cheeks warming with the realization that she'd been staring. She skimmed the options. It was mostly burgers, sandwiches, and a few salad options. "I'll get the cheeseburger too," she decided.

Chandler set his menu down but didn't pull his hands away. Instead, he fidgeted with the edges, his fingers tracing the laminated corners like they gave him something solid to hold on to. He must be as nervous as she was. "We should start with the easy stuff," he said, glancing up at her with a half-smile. "How old are you?"

"I'm eighteen," Monica said with a light chuckle, amused by the icebreaker. "What about you?"

"Nineteen," Chandler replied, giving her an easy smile. It softened his whole face. "Is Ross your only sibling?"

Monica nodded, "Yup, one older brother. Did he happen to mention that he's the golden child?"

Chandler leaned back slightly, grinning. "I might've heard that once or twice. He said he was a miracle baby."

Monica groaned, sinking into her seat as if the very words physically pained her. "God, I'm sorry you have to put up with him. But I had to live with it for sixteen years, so I don't feel too bad for you," she said honestly, which made him laugh. A sense of pride filled her for a second when she heard it. His laugh is quick, and he looks down like he's embarrassed about it, but he shouldn't be.

Their waitress appeared at the side of the table, setting down two glasses of water with a clink. She looked barely older than them, probably college-aged, with a tired smile and a notepad in hand. Monica placed her order for a cheeseburger and fries, and Chandler followed suit, adding a chocolate milkshake to his. The waitress nodded, scribbled, and vanished into the hum of the busy restaurant. Once she was gone, Monica turned her attention back to Chandler, who was already looking at her with curiosity.

"So," he said, tilting his head, "what's the reason you couldn't get a real date for this?"

The question was innocent enough, but Monica still felt her stomach twist. "I asked a few guys at school," she said with a shrug, trying to sound nonchalant. "They were either busy or uninterested. My roommate Georgia thinks they're just intimidated, but... I'm not buying that."

"I don't find you very intimidating," Chandler said, resting his chin in the palm of his hand. His elbow was propped up on the table, his posture easy and open. "Unless you're trying to be intimidating. Are you?"

Monica could only chuckle at his weak attempt at flirting. Her only experience with romance so far was romantic movies and her parents. Frankly, watching her parents flirt made her skin crawl. However, in the movies, men seemed better at flirting than Chandler was. By the way he sat up straighter, her small laugh clearly gave him a boost of confidence. "It's not really what I'm aiming for."

Chandler shrugged, unabashed. "You seem nice. I wouldn't worry too much. You're only eighteen after all, it's not like you're old."

"That doesn't matter to my mother," Monica sighed, exhausted just by thinking of her. "She basically thinks I'm already past my prime and no guy will give me the time of day. When I told her I was with someone, I wasn't planning on lying, but she was just going on about how great Ross is, and he's bringing his girlfriend. I had to say something."

"Is it really that bad?" Chandler asked with a worried expression on his features. "Ross has told me stories, but I didn't think they were too terrible."

Monica laughed, but it lacked humor. "Oh no. If anything, he sugar-coated it. Ross sees her through this perfect, warped lens. He's like they're little prince, so he can never stand up to them even when they throw me under the bus. You don't have any siblings, do you?" she asked, needing a change of subject.

He shook his head, "Nope, only child. My parents got divorced when I was a kid."

Monica looked back at him, surprised by how casually he'd said it.

He gave a wry smile and leaned slightly closer. "Actually, they told me about the divorce on Thanksgiving."

"Oh my God! That's why you hate the holiday?" She guessed, her voice rising with disbelief.

Chandler nodded, rubbing the back of his neck sheepishly. "Yeah… I threw up my dinner right after they told me. Not my finest moment," he said with a self-deprecating laugh, eyes lowering to the table. "Now the whole meal just makes me queasy. It's weird—I can eat turkey sandwiches or mashed potatoes any other time of the year, but Thanksgiving dinner? Instant nausea."

"Sounds like your stomach has PTSD," she said softly, her voice gentler now as she took a sip from her water.

Chandler let out a breathy chuckle, glancing up. "Yeah. I guess so."

"This is good," Monica said with a newfound sense of enthusiasm. She pulled a notepad and pen from her purse and began writing. "We should get to know each other more so it's more convincing."

"Do you carry that thing around everywhere?" Chandler asked, tilting his head, brow lifting in surprise.

"Yeah, everybody should be carrying one. How else would you write down important things?" Monica questioned. There wasn't a point in letting him answer as she prepared her notes for her questions, like an interview. "Okay, what's your major?"

"Computer science," he said as he watched her. Monica was used to getting odd looks for being overprepared, but she didn't see anything wrong with being ready for every scenario. She glanced up at him as he continued, "I just want a decent job. Something stable. I've never had, like... a big passion or dream or whatever."

Monica paused mid-scribble. "None at all?"

He looked back at her and smiled faintly. "I mean, not yet. I figure I'll get a job, save up for a few years, and once I've got some breathing room, maybe then I'll figure it out. I'd like to dosomething... I just don't know what it is yet."

She nodded slightly, "I'm sure you'll find something. I didn't find my passion for cooking until last year. I think it works differently for everyone."

"Ross said he found his passion when he was six," Chandler muttered.

Monica rolled her eyes with an exasperated groan. "Okay, that's definitely a lie. He's majoring in paleontology because his best friend dared him to do it."

Chandler chuckled. "So, your brother's a compulsive liar."

"Only when it makes him look smarter or more accomplished than he actually is," Monica said with a huff. "Which is, like, all the time."

She flipped the page on her notepad, "Let's figure out a backstory. We're going to need something to tell them when they ask how we met."

He groaned as if he had just assigned homework. "We could tell them that we met in detention. I was the boy who annoyed you all day, and you were the princess. After we shared our heartbreaking backstories, we learned to tolerate each other."

"Doesn't that happen in The Breakfast Club?" Monica asked, confused.

"Maybe," he muttered.

"Okay, well, for starters, we didn't go to the same high school. I never got detention. And I definitely wasn't the princess type in school."

Chandler grinned. "I could see you being the brain."

"I was," she said flatly.

"Explains the notebook."

Monica rolled her eyes and groaned, "We need to focus. We're going to need a plan to be prepared when we get there." Monica insisted. She tried to think of a story that was realistic enough that her mother would believe. That was the hardest part, given that her mother didn't think it was even possible for someone like her to get a date.

"I got it," Chandler said quickly. "Why don't we say we met at summer camp? I helped you learn how to dance, and you were clumsy at first, but-"

"That's Dirty Dancing," she rolled her eyes, interrupting him. Monica was starting to become annoyed with him for not giving her anything actually useful. "It only came out a few months ago, you think they wouldn't notice?"

He just shrugged, seemingly calm about the whole situation, while Monica tapped furiously at the page. Her anxiety, which had briefly subsided, returned like a wave. She hated how her heart raced just thinking about her mom's judging stare, the passive-aggressive compliments, the barely-veiled comments about her weight, her future, hervalue."Can you take this seriously for two seconds?"

Chandler rolled his eyes, but leaned closer to the table, focusing all his attention on her as his expression softened. "Come on, Monica. Do you really think we need some elaborate story? It's just your parents. Ross said it wasn't a big deal."

"You don't know my parents," Monica said flatly. Her eyes snapped up to meet his. "And the first rule of being my fake boyfriend—neverlisten to Ross."

"Okay, fine," Chandler grumbled.

It was clear he was already tired of her domineering nature. His smile was gone, and the light in his eyes was replaced with a look of complete boredom. It irritated her more than she cared to admit. She'd been called "bossy" her entire life, but watching Chandler tune her out made her feel, for the first time, genuinely annoying.

Still, she wasn't sure she likedhimall that much either.

Sure, he was quick-witted and could crack jokes, but there was something immature about the way he deflected everything with humor. They were technically adults now (college students), about to spend an entire holiday break playing couple in front of her family, and he was still acting like a teenage boy who ordered chocolate milkshakes and couldn't hold a serious conversation for more than thirty seconds.

She couldn't picture a future with someone like that. If she wanted to fulfill her dream of becoming a Mom of three with the perfect husband, she couldn't waste time with guys like Chandler. But none of that mattered now. They were leaving for break in less than a week, giving them only six days to prepare to appear cordial, at the very least.

"I say let's keep it simple," Monica said, her pen already scrawling across the notepad. "We've been dating for two months. Long enough that it's not weird to bring you home, but not so long that they'd question why I never mentioned you before."

Chandler gave a dramatic sigh, eyes toward the ceiling. "Wow, two months already? This relationship is moving so fast. I still remember the day we met like it was... twenty minutes ago."

Monica didn't look up from her writing. "Cute."

He grinned, but she didn't return it. Instead, she continued quickly, as if ignoring him might keep things on track. "Let's say we met through Ross. I went to visit him after the semester started, he introduced us, and you called me later. We started talking, went on a date, the rest is history."

"This all seems kind of obvious," Chandler said, watching her fill a second page with notes. "Do youreallyneed to write it down?"

"Honestly? I don't trust you to remember it. Our stories need to match to make sense," she explained.

He rolled his eyes. "Fine, fine. What's next? Our imaginary anniversary dinner menu?"

Monica narrowed her eyes at him. "What kind of boyfriend are you?"

Chandler blinked. "What?"

"I mean, are you the kind of boyfriend who calls me every night and brings me flowers on weekends? Or the kind who vanishes for days and only calls when he needs something?" She asked. She might not have had a boyfriend yet, but her high school friend, Rachel, had plenty. She knew what guys could be like.

"Uh, wow." Chandler leaned back in his seat, caught off guard. "Is that a serious question?"

Monica stared at him, waiting for his answer. She wasn't in the mood to play games, especially if he wasn't going to focus on the task at hand. Of course, she was aware of how harsh she was being, but once she focused on something, it was hard to stop.

He eventually sighed, reluctantly answering the question. "If I like a girl, I end up more clingy than she is."

"Really? Speaking from experience?"

"He hesitated. "I haven't... actually dated anyone. Like, not seriously," he confessed, seemingly ashamed of himself. Chandler scratched the back of his neck, looking uncomfortable. "I went on a date in my freshman year. She was nice, and I liked her, but I freaked out and just didn't call," he said with a small shrug.

Monica frowned at this. He was just another one of those jerks who never called after a date, leaving girls wondering why they weren't good enough to go out again. The only decent thing about it was that he seemed to be remorseful. "How could you do that to someone?"

"I don't know! It was my freshman year. It was stupid, I just got scared," he muttered, avoiding her gaze.

Monica wasn't afraid to take charge. If Chandler was nervous about having a girlfriend, real or not, Monica was happy to help him. "Even if you're not that kind of guy, you're going topretendyou're that kind of guy. That means you call me once a week, we go on dates every Saturday, and you sometimes bring me flowers. Got it? My dad won't like you if you leave me without even a phone call first."

"Wow, how much have you thought about this?"

"I haven't really, I just want to be prepared, that's all," She mumbled. She didn't want to see the judgmental look that everyone gave her when she was 'overprepared' and 'neurotic'. "Do you have any questions about this so far?"

"I was only hoping to learn more about you. Y'know, your likes, your dislikes, who you are. I wasn't expecting a crash course on a fake relationship."

Their conversation was temporarily interrupted by the waitress coming back with their food, carefully setting the plates down for them. The food was hot, she could see the steam coming from the fries on her plate, and her stomach rumbled, making her realize how hungry she was.

"Can I get you anything else?" The waitress asked, setting his milkshake down.

"No, thank you," Chandler smiled politely, sliding his milkshake closer to himself, like an excited child before eating the bright red cherry off its stem. Monica couldn't help but arch an eyebrow as he immediately took a long sip through the straw.

Both of them dug into their food, satisfying their hunger and taking a break from planning the situation they've found themselves in.

"So, what kind of things do you like?" Chandler asked, wiping the corner of his mouth with a napkin. "Do you watch TV?"

"Of course, who doesn't?" Monica smiled slightly, relaxing from their more tense conversation before. "I like talk shows, but I love game shows. Pyramid is one of my favorite shows of all time."

"Pyramid? Seriously?" Chandler chuckled.

"Yeah! It's the best game show out there. Have you seen it?" Monica asked brightly, excited for an opportunity to talk about her favorite television show. Game shows were typically the only shows she and Ross could agree on watching, so they watched them the most. "Also, Win, Lose, or Draw is amazing."

He stared at her for a moment, "You're a lot like your brother, you know that?"

Monica's expression shifted. Her eyebrows drew together slightly in confusion. "What do you mean?"

"It's not a bad thing. You both get so…" Chandler waved his fingers vaguely as he tried to think of the word. "Peppy, when you get excited."

"Peppy?" Monica laughed. "I don't think I've ever been called peppy before. Organized, maybe. Intense, definitely. But peppy?"

He shrugged, sipping his milkshake again. "Hey, it's not a bad quality. So, you're a chef who likes game shows, what else do you enjoy?"

"I like reading fantasy books or romance books, mostly. I also like sports, but my parents don't let me play anymore. I'm too competitive, apparently."

Chandler tried not to laugh, but a small snort escaped anyway. "Yeah… that makes a lot of sense."

"What'sthatsupposed to mean?" Monica narrowed her eyes, but the corner of her mouth twitched.

"Well, if you're writing a novel about our fake dating life, I wouldn't want to see how you are on a team," he smiled. "You were probably the one who took it too seriously and punched your teammates when you lost."

"Only because I'm passionate," Monica defended. "In my opinion, they never took it seriously enough."

"Passionate, right," Chandler teased, nodding. "Is that what we're calling it?"

She rolled her eyes with a slight smile. "Okay, your turn. What aboutyou?What doyoulike, besides milkshakes and making jokes?"

Chandler leaned back, looking thoughtful. "Hmm. I played hockey for a while when I was growing up. Not to brag, but I did win a trophy."

"Was it real or, like, participation?" Monica teased.

He looked at her with shock in his eyes that she had the wits to match his before he smiled, resting his elbow back on the table. "Hey, I showed up to every practice and skated around that rink. I earned it."

"Participation, got it," she chuckled. "Either way, you don't look like the athletic type to me."

"Well, hockey's still probably my favorite sport. But I also really like baseball. The Toronto Blue Jays are my favorite team, and before you say anything, yes, I know we're in New York," he added quickly, almost like people have criticized his favorite team in the past. "But, my Mom would take me up to Canada and we'd go to games sometimes while we were there."

"That's cute," she said with a soft smile. "What else?"

"I also like to read, so we have that in common. Nothing specific, though, usually whatever grabs my attention. Sometimes biographies, sometimes comic books," he said with a slight shrug.

"Well," Monica said, sitting back and sipping her drink. "At least we're not completely incompatible."

"Oh no," Chandler said with mock horror. "You'redefinitelyout of my league. But I'll fake-date you anyway."

She smirked playfully. "Lucky me."

Then, her tone shifted, turning more businesslike. "Speaking of which… we should talk about boundaries. I'm thinking we should at least hold hands. My mom might be suspicious if we're not at least a little close, right?"

Chandler let out a small sigh, already bored with this entire plan. "Wow. You're making romance sound like a dentist appointment," he muttered.

"I'm sorry, but this is important to me," Monica said firmly, her voice a little defensive. "So, holding hands, sit next to me and in the worst case scenario, we might have to kiss, okay?"

"Kissing me is the worst scenario for you? Don't I feel special," he muttered sarcastically.

"That's not what I meant," she groaned, rolling her eyes and grabbing the notepad again."Just, worst case, my parents expect us to be…affectionate. My mother definitely won't believe we're a couple. If we're affectionate with each other, then she won't doubt it anymore."

"But we're not a couple," Chandler pointed out. "Can't you just tell your Mom that you're looking around? You're pretty enough to get dates."

Monica shook her head, "I told her that I'm already with someone. I wouldn't be doing this if I weren't desperate. If I don't show up with a guy, I'll never live it down. So, are you okay with kissing me if you have to?"

He hummed, looking up at the ceiling dramatically, then smirked like the answer was obvious. "Am I okay with kissing a hot girl? Man, what a difficult decision. I may need a moment to think."

"Shut up," Monica murmured, her cheeks a faint shade of pink. She was never good at getting compliments. Typically, she assumed the person giving them was just trying to be nice or throwing her some kind of bone. Chandler has been complimenting her since he walked in, and by now, he was laying it on thick.

"Obviously, it's fine. I couldn't actually get a girl like you to go out with me in a million years. This is really a once-in-a-lifetime opportunity," Chandler smiled, his tone suddenly more sincere.

Monica's expression tightened. "It's only in case ofemergency," she clarified, folding her arms over her chest. "I want my first kiss to mean something, not just be some show for my parents."

She knew what guys in college were like, casual and uninterested in things like romance or a real emotional connection. Monica wasn't naive. Most of them didn't think past the next party or the next hookup. Chandler probably didn't care about any of was a possibility that he wasn't one of those guys, but she didn't know for sure.

Chandler was watching her, and she couldn't tell what he was thinking, but eventually he put his hands up in a slight gesture of surrender. "I promise I'll take this seriously when it matters. I mean, unless you want me to start planning our fake honeymoon, in which case, Paris is looking pretty good."

Monica didn't answer. She just exhaled sharply through her nose as she ignored the comment. Monica wondered if he was always like this. Making sarcastic remarks about everything and being unable to take anything seriously. All she could do was hope that when they got there, he would be convincing enough. Maybe this wasn't going to be as easy as she thought.