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Author's Chapter Notes:
Hey everyone I wanted to get an update out as soon as I could. I have a general story idea of how to do this, but the setup was the hardest part! I'm excited to write the next and following chapters! continue to review or jellybean this story and I will update quicker promise! Also, if anyone is interested in being a beta reader for this story reach out to me through the reviews or MTT discord! Enjoy!

The weekend seemed to drag on, and by the time Sunday evening finally arrived, Jim found himself in the Dunder Mifflin parking lot with his suitcase, nervously tapping his foot while he waited for everyone else (and Pam) to arrive. Everyone except Michael and Pam had shown up, and as soon as Jim began to zone out, Dwight stood up.

“Okay, people, I need to know if anyone is carrying any liquid items over 3.4 ounces or any illegal weaponry of any kind. The weaponry will be confiscated now and returned upon safe arrival back from the trip,” Dwight said, walking around with a notepad in hand.

Stanley rolled his eyes. “Just great.” He sighed and put his neck pillow on, opting for a nap while waiting for Michael.

Dwight glared at Jim as he walked by. Jim responded, “I’m carrying a weapon. However, I’m trained to use it.”

Dwight immediately stopped and stared at Jim. “I need to have the weapon unless I can see some identification or qualification, at my discretion.”

Jim shrugged. “I was taught by my father’s friend, although they ended up becoming enemies.”

Dwight continued staring. “I need to see the identification, Jim, or else the weapon will have to go into my arsenal.”

“Like I said,” Jim replied, “I was taught how to use it and was told it was the weapon of my order as well.”

“Jim, if you’re carrying a lightsaber, it must be handed over to me. Unfortunately, the Jedi Order no longer exists due to Order 66. And even if it did, they would never consider you to be a Jedi.” Dwight’s tone was firm.

Jim gasped in mock shock. “But I was told I’m Force-sensitive. Dwight, the leader of the Empire will be at Disney! How else will we fight him?”

“I’ll fight Darth Vader if it comes to it myself,” Dwight shot back. “I’ve been told I resemble a young Han Solo, and I have to agree with them. Also, Force-sensitive people or children don’t exist, Jim. Why don’t you try living in the real world sometime?”

Jim spotted Pam leaving their truck in the parking lot and heading toward the lobby—right at the perfect moment.

“Oh really? Watch this, Dwight.” Jim stood up and held his hand out in front of him as Pam walked through the doors.

Pam was immediately surprised by the scene unfolding before her and stood still long enough for Jim to catch up.

“Pam, can you believe Dwight doesn’t think I’m a Jedi or that I can use the Force on people when I need to?” Jim raised his eyebrows and winked at her, signaling her to "go with it."

Pam picked up on it, stopping in her tracks and sighing. “Jim, how many times have I told you not to use your Force to make people stop in their tracks? You’re supposed to be one with the Force and only use it for good. Remember what Obi-Wan said.”

Jim immediately lowered his hands, faking heavy breathing. “Sorry. I guess sometimes I don’t even know my own power.”

Pam stumbled forward, as if someone had removed an invisible wall from in front of her. “Jim, you know fear leads to anger, and anger leads to hate, which leads to suffering.”

Jim shook his head, struggling to hold it together as Dwight watched the entire exchange with a serious look on his face. He then looked back at Jim and said, “I still don’t believe you’re a Jedi, but it’s good to know for when we near Star Tours.” He scribbled something on his notepad and walked away.

“Hey, Eeyore, you’re almost late. You’re lucky you didn’t miss whatever Michael is about to pull. He’s probably gonna come dressed as Aladdin and try to ride a carpet attached to wheels,” Jim teased.

Pam giggled. “Yeah, sorry. Roy was being really lame about this whole trip the entire weekend. He was super upset about me having to leave for a week while he still has to work. He probably just wanted someone to pick him up from the bar whenever he or his buddies get too drunk to drive.” She said it in a frustrated tone, but then her eyes went wide as she realized what she had just confessed.

Before Jim could respond, Michael barged in with a burst of enthusiasm, wearing a neon pink Mickey Mouse-shaped hat that looked more like a highlighter.

“All right, all right! The magic begins now! Who’s ready for a week of inspiration, teamwork, and memories that will last a lifetime?” Michael shouted, his energy practically bouncing off the walls.

Jim and Pam exchanged a look and both started laughing as Michael led everyone toward their shuttle to the airport.

“Let’s load up the bus!” Michael continued, his excitement undeterred. “We’ll kick things off with a rousing game of... well, it’s a surprise! But let’s just say, there will be a lot of running around and bonding! Right, Dwight?”

Dwight, who had already positioned himself next to Michael, nodded seriously. “I have a detailed schedule of every activity, every meal, and every moment of downtime. This trip will be the most productive vacation in the history of Dunder Mifflin.”

“Good man!” Michael clapped Dwight on the shoulder. “All right, everyone, to the buses!” He said, attempting a British accent.

Jim took a deep breath as they all filed out of the office and into the parking lot. “Here we go,” he muttered to Pam.

She smirked, tugging her suitcase behind her. “At least it’s just one week... we’ll survive.”

“At this point, I’m hoping we get through security with Dwight,” Jim laughed as they loaded onto the bus.


Once they were on the bus headed to the airport, Michael stood up from the front and turned around to face them. “Alright, team! This is it! The adventure of a lifetime. You’re about to experience Disney World like never before. But remember, this is a work trip! No one is off the clock!” He gave a thumbs-up and a grin so wide it could have cracked his face.

Stanley rolled his eyes, muttering something about "life already being too much of a theme park." As usual, his neck pillow was firmly in place, ready for the inevitable nap.

“Alright, I thought we could kick off the week by getting into the Disney spirit. Whoever I see with the most spirit by the time we get to the airport gets bonus points for our challenge this week!” Michael had a “Disney playlist” blaring through the speakers, and Jim couldn’t help but chuckle as “Hakuna Matata” started playing.

“Yeah, this is happening,” Jim whispered to Pam. “Michael is going full Disney. I’m half-expecting him to start singing ‘It’s a Small World’ next.”

Pam snorted quietly. “Well, we are about to board a plane with Michael Scott in charge. I don’t think it’s out of the realm of possibility.”

Once they arrived at the airport, Michael was the first off the bus and practically skipped toward the check-in counter, dragging Dwight behind him. Dwight, as expected, had already started planning the trip’s logistics and began passing out what looked like detailed schedules to everyone.

“Don’t forget, every second of this trip is valuable,” Dwight said in his usual, intense monotone. “There’s no room for leisure unless it’s on the agenda.”

Jim turned to Pam, rolling his eyes. “I think this trip is going to be more military than vacation.”

Pam sighed and shook her head. “We’re in trouble, aren’t we?”

“No way,” Jim replied, grinning. “We just have to convince Dwight that Disney is full of potential clients waiting to be had, and he won’t care about bossing us around anymore.” He winked at her.

As they went through security, Dwight was in full interrogation mode. “No liquids! No snacks above approved weight!” He pulled out his own metal detector wand and waved it around like he was searching for nuclear material. Jim stood there with his hands raised in mock surrender, but Dwight didn’t seem to appreciate the humor.

“Jim, if you think that’s funny, you’re more likely to find yourself spending the night in a holding cell than at Disney World,” Dwight warned, eyeing him suspiciously as Jim walked through the scanner.

“I’ll keep that in mind, Dwight,” Jim replied with a smirk. “But it might be hard to make it to the happiest place on Earth when I’m detained for ‘carrying suspicious snacks.’”

Pam shook her head. “Hey, I’m just saying, Pringles are the way to go, Jim. I’ve never gotten in trouble for eating them.”

“Oh no, I’m still choosing Beesly.” Jim said, picking up his shoes after going through the detector as they headed toward their terminal.

As they gathered their things and made their way to the gate, Pam leaned over to Jim, whispering, “What do you think the chances are that we board the plane without Michael announcing something ridiculous?”

Jim glanced around at the group, who seemed somewhere between annoyed and bewildered by Michael’s antics. “I give it... two minutes. Maybe less. We doubling down on the snack deal?”

“No way. I’m already too deep in the hole,” Pam replied.

Sure enough, Michael wasted no time. He gathered the group together in front of the gate and began a speech that could only be described as over-the-top and entirely unnecessary.

“Alright, everybody! As we take off on this incredible journey, I want you all to know this trip will change your lives. Remember, you’re not just going to Disney—you’re going to an experience that will reshape the very core of who you are! We’re going to be more than just a team. We are going to be a family. A Dunder Mifflin Disney family!”

Jim turned to Pam with a deadpan expression. “So, how many people do you think are second-guessing flying with us or thinking we’re a cult?”

Pam stifled a laugh, her eyes sparkling. “At this point, I think we’ve crossed over from ‘team-building’ to ‘Team Disney Mifflin: The Reality Show.’”

With around 20 minutes until their flight left, Jim decided to cash in on his snack win.

“Hey, Beesly, I’m getting pretty hungry here and could really go for some Chex Mix.” Jim emphasized the Chex Mix.

“Alright, let’s just get this over with. At least I can get myself Pringles, too,” she said as they got up and walked over to a snack store in the airport.

Jim grabbed a Scranton magnet from the store and said, “Man, I wonder who has this on their fridge. Like, imagine coming here on a layover, going to the store, and saying, ‘Yes, I do want to commemorate this trip with a Scranton magnet and some Doritos.’” He put the magnet back on the shelf.

“Only you, Halpert,” Pam said with a chuckle, shaking her head as they made their way to the snack aisle. “Who even thinks about stuff like that?”

Jim grinned, grabbed a bag of Chex Mix from the shelf, and tossed it into their basket. “I like to think of it as a unique perspective on travel. You know, making memories with every snack.” He winked at her.

Pam rolled her eyes, but her smile was warm. “You’re something else.”

“Yeah, sure. One of a kind,” he said, winking again as he grabbed a pack of Sour Patch Kids for them to share. Pam then realized he was wearing a jersey with his name on the back in fading letters and smiled.

“Wow, can’t believe you still fit into your high school jersey, Halpert. Are you ever gonna grow taller?” she said with a smirk.

Jim looked down at his jersey, the familiar number 23 faded from years of use. He shrugged nonchalantly, still grinning. “Well, you know what they say, Pam—once you hit perfection, there’s no need for growth.”

Pam snorted and playfully nudged him with her shoulder. “Perfection, huh? You’re really leaning into the ‘peak high school’ look.”

Jim held his hands up in mock surrender. “Hey, I’m just here for the snacks and the memories. Plus, this jersey has sentimental value. It’s been through a lot with me.”

Pam raised an eyebrow. “Sentimental value, huh? What’s the story behind it?”

Jim grinned, clearly enjoying the tease. “Well, it was the year I won the championship for my team—when I was the undisputed king of the court, obviously. People still talk about it…”

Pam burst out laughing. “I’m pretty sure you’ve mentioned that one before. More than once.”

“Yeah, but it's an important part of my history,” Jim said dramatically, puffing out his chest as if delivering the greatest speech of all time. “You can’t just forget moments like those. Plus, you saw the king of the court back in his natural habitat a little while ago, in the warehouse game.”

Pam rolled her eyes but couldn’t help but smile. “Alright, Halpert, I get it. You peaked in high school. You’re a legend. You don’t need to remind me.”

“I’m just trying to keep the legacy alive,” Jim said, winking as he tossed the Sour Patch Kids into their basket. He could tell Pam was genuinely enjoying the banter, and he was more than happy to keep it going.

They continued down the aisle, gathering snacks and giggling at the absurdity of it all, until they were finally ready to check out. As they walked to the counter, Jim caught Pam glancing at his jersey again, clearly trying to hide the smile creeping up on her face.

“I’m just saying, that jersey’s classic. You can’t replace the nostalgia,” Jim added, his tone turning more serious, though the playful spark in his eyes remained.

“I can’t argue with that,” Pam said, her voice softening as she glanced at him. “It’s kind of cute, actually. The whole ‘high school legend’ thing.”

Jim’s eyes lit up. “Wait, did I hear that right? Did you just say I’m cute?”

Pam’s cheeks flushed and her face was completely red, but she managed to still smirk. “I said the jersey is cute. You’re... well, you’re not exactly a gentleman making a girl pay for his snacks.”

Jim’s eyes widened, feigning shock. “Oh, so now I’m a loser, huh? You’re just gonna throw me under the bus like that, Beesly?” He grinned, clearly enjoying the playful back-and-forth.

Pam rolled her eyes, but the warmth in her smile gave her away. “I didn’t say loser... I said you’re not a gentleman. Big difference.”

Jim placed a hand over his heart in mock hurt. “I’m crushed, Pam. I thought we had something special.” He leaned in a little closer, his voice dropping to a dramatic whisper. “But I guess this is it. The end of the Halpert legend.”

Pam couldn’t help but laugh at his theatrics. “You really are something else.”

As they walked back toward the others, Jim couldn’t help but feel like this trip, ridiculous as it was, was shaping up to be one of those small moments he'd look back on with a smile. Sure, Michael was going full Disney-crazy, and Dwight was taking his role as trip enforcer to the extreme, but there was something about the simplicity of walking through the airport with Pam, teasing each other and getting lost in the little jokes, that made it all feel worth it.

Pam nudged him again, snapping him out of his thoughts. "You know, you're still not getting away with the whole 'Jedi' thing, right?"

Jim smiled mischievously. "Oh, I’m just letting Dwight catch up. He’s not quite ready for the power of the Force yet."

Pam raised an eyebrow, looking amused. "You're really sticking with that, huh?"

"Absolutely. The Jedi don’t give up that easily," Jim said confidently.

Pam sighed with a smile. "Well, just make sure you don't get caught in a lightsaber duel with Dwight before we even get to the hotel."

"Don't worry. I can take him," Jim said with a wink. "I’ve got the Force... and the snacks."

As they boarded the flight, the usual chaos continued—Michael singing along to whatever Disney song he could find, Dwight obsessively taking notes about team dynamics, and everyone else just trying to survive the madness. Jim couldn’t help but watch Pam out of the corner of his eye, still feeling the subtle shift in her energy. She hadn’t seemed distracted earlier, but now she was more present, chatting with Phyllis about the best Disney snacks while avoiding any eye contact with him.

That’s what friends do, he reminded himself. They just talk and joke. Nothing more. He just had to keep his head in the game, enjoy the trip, and—maybe—let things unfold the way they were meant to.

But there was still that weird, fluttery feeling in his chest when she laughed. That’s all, he told himself.

At some point, Jim leaned over to Pam as Michael started another one of his impromptu, over-the-top “motivational speeches.”

“Uh-oh. Michael’s gearing up to announce ‘Dunder-Disney Team-Building Challenge 2006,’” Jim whispered, raising an eyebrow.

Pam rolled her eyes but couldn’t help the smile tugging at her lips. “I swear, he’s the only person who could make a Disney trip feel like boot camp.”

Jim chuckled softly. “Well, with Dwight as his second-in-command, we might actually get some ‘work’ done in the middle of all this madness.”

“Like, what? Building trust falls into Disney princesses?” Pam teased.

“Exactly. Trust falls into Cinderella’s pumpkin carriage,” Jim quipped back, grinning.

Pam’s smile widened, a genuine spark lighting up her eyes as she turned to face him. “I’m in. Who do we need to throw under the carriage?”

Jim laughed, leaning back in his seat. “Don’t worry, I’ve got it covered. I’ve been training my whole life for this moment.”

They both laughed together, but as the sound faded, Jim found himself lingering a little longer than usual, just looking at her. There was something in the way she smiled that made him feel—what? Like everything was right with the world for just a moment, like he could just be... himself. But he knew it wasn’t as simple as that.

Pam quickly turned her attention back to her book, and the moment slipped away.

Jim let out a quiet breath, pushing his thoughts aside. He really didn’t want to overthink it. They were friends, and that was enough for now.

When they finally landed, the chaos of the airport only heightened. Michael’s excitement was practically radiating off him as he clapped his hands and ushered everyone toward the luggage claim.

Jim and Pam were at the back of the group, trailing behind as they both rolled their suitcases toward the exit.

"So, which Disney park are you most excited for?" Jim asked, trying to keep things light.

Pam thought for a second, her hand absently playing with the strap of her bag. “I think... maybe Epcot? I’ve always wanted to try those frozen margaritas in Mexico.” She raised an eyebrow at him playfully. “You in?”

Jim smirked. “That sounds like something I can get behind.” He glanced at her, the idea of exploring Disney World with her—just the two of them—suddenly sounding perfect.

But before he could voice anything, Michael was already shouting out directions. “Alright! Team! The adventure begins now! To the shuttle! We’re headed straight for the magic!”

Pam shook her head with a grin. “Here we go.”

Jim smiled, feeling that familiar sense of calm whenever Pam was near. Sure, things were still weird—especially with her fiancé waiting back home—but for now, at least, he was just happy to be here. With Pam.


As they loaded the bus to head to the Disney World resort, Michael cranked up the Disney playlist again. To Jim’s surprise, he found himself singing along to a few songs. Everyone joined in on “You’ve Got a Friend in Me,” and Jim couldn’t help but laugh. Turning to Pam, he found her singing too, and for a moment, he realized this trip might actually be pretty fun.

The bus ride to the resort went by quickly, and soon enough, they pulled up to Port Orleans French Quarter, a charming resort nestled alongside a flowing river. The exterior was cozy and colorful, with ironwork balconies and winding brick paths lined with lush greenery. It felt like a quiet corner of New Orleans had been plopped right into the middle of Disney World—whimsical but not overdone.

The lobby had an unexpectedly serene vibe compared to the chaos of the bus ride. There was a person playing the piano, and the space had an elegant 1900s European theme. Jim couldn't help but smile at the thought of Michael and Dwight interacting with the hotel staff. He had already mentally prepared for the awkwardness that would surely follow.

Pam, however, seemed to be taking everything in stride. She paused to admire the intricate details of the lobby, a look of genuine awe on her face. “This place is incredible—way nicer than any hotel I’ve ever been in,” she said, scanning the vibrant decor.

“Yeah, it’s a bit of a step up from the usual hotels I stayed in on family vacations,” Jim replied, watching her take it all in. “Too bad we’ll probably never actually experience this resort without some kind of... complication.”

Pam shot him a knowing smile, her eyes twinkling with mischief. “With those two? No chance. But I’m still looking forward to it.” She subtly nodded toward Michael and Dwight, who were already deep in conversation with a hotel employee about the best place to get a “real” margarita while trying to check in their group. “At least it’ll be entertaining.”

As the group gathered around Michael, who was now standing behind the front desk with an exaggerated grin, Jim could already tell this was going to be an interesting experience.

“Alright, people!” Michael called out, drawing everyone’s attention. “I’ve got your room keys right here. Get ready for the Disney vacation of a lifetime!” He waved the stack in the air dramatically, his face lighting up with a level of enthusiasm only Michael could muster. “Now, don’t just take your keys and run—this is a big deal. We’re going to experience Disney like royalty! Don’t forget to tip your housekeeping staff!” He waggled his eyebrows at the group, as if he were imparting some great secret.

Dwight was already handing out keys with military precision, ensuring that the “important” people got theirs first. Jim was half-watching Dwight and half-watching Pam across the room, who was happily chatting with Kelly and Phyllis about something.

Jim turned back to Michael, who was now calling out names. “Jim Halpert, Room 223! You’re with... ugh, Toby. I guess it had to be somebody. Sorry, Jim,” Michael said, too enthusiastically for what should have been a simple room assignment. “Unless you want to stay with me in my luxurious suite, pal?”

“That’s okay,” Jim said a little too quickly and walked over to Toby.

“So, you ready for this, Toby? Ready for the magic?”

Toby glanced down at his room key, then back up at Jim. “I don’t know, Jim. I’m just here to avoid any more emotional breakdowns.” He gave a tired shrug, clearly ready for a quiet, uneventful trip. Jim laughed, feeling a little lighter just by having someone to joke around with.

As they were talking, they glanced back at Michael, who was still dramatically waving keys in the air, shouting something about "Disney magic" and "royalty treatment." Jim couldn't help but shake his head. Only Michael could turn a simple room check-in into a Broadway performance.

Toby, still holding his key with a resigned grip, sighed. “I swear, if Michael starts asking me to lead a sing-along or something, I’m going straight to the gift shop to buy a drink,” he muttered under his breath.

Jim couldn’t help but laugh. “Don’t worry, Toby, he’s probably going to make a big speech about how Disney was built on dreams and friendship any minute now.” He raised an eyebrow, mimicking Michael’s overly enthusiastic gestures. “I just hope he doesn’t start assigning us roles like we’re on some weird Disney-themed reality show.”

Toby gave a dry chuckle, glancing at Michael, who was now performing an impromptu rendition of “A Whole New World” to an increasingly bewildered group. “It’s either that or we end up in one of those cheesy team-building trust exercises.”

Jim shuddered dramatically. “Nope, I’ll pass. Let’s just get through this without any ‘trust falls’ or motivational speeches, and I’ll call it a win.”

Jim and Toby then made their way over to the rest of the group. Kelly, who had been keeping an eye on the situation with her usual level of excitement, skipped over to Pam, practically bouncing on her heels. “Pam! Pam, I just realized! We have to get a picture with the castle on our first day. Like, it's mandatory. We can do a cute little ‘Disney BFFs’ pose and put it on our MySpace profiles!”

Pam laughed, clearly amused but also indulging Kelly’s enthusiasm. “Sure, Kelly. But only if we get matching Minnie ears first, okay?”

Kelly’s eyes widened in pure delight. “YES! You get me, Pam. You totally get me.”

As Dwight finished handing out room keys, Michael got everyone’s attention. “Alright, Dunder Magic Team, head to your elephantic rooms and change into some clothes. We will meet for dinner and some team-building in the dining room in 30 minutes! Don’t be late!”


As they continued walking down the hallway toward their rooms, Jim glanced over at Pam, Toby, and Kelly, an idea forming. “So, what do you think? Skip the whole ‘team-building’ dinner with Michael and hit up Downtown Disney instead?”

Pam shot him a playful look. “Definitely. I don’t know if I can take another speech about ‘believing in the magic’ and ‘Dunder-Disney energy.’”

Toby nodded, already mentally checked out. “Yeah, I’m all for avoiding whatever weird exercise Michael has planned.”

Kelly, already pulling out her flip phone, chimed in. “Oh my god, yes. Dinner with them? Ugh, I can’t even. Downtown Disney is so much better. I’ll text everyone and we’ll make it so cute on MySpace later. I’ll tag you guys in everything.”

Ryan, who had been walking a few steps behind and had been quietly listening, suddenly perked up. “Did you say Downtown Disney? That’s, like, way cooler than whatever Michael’s trying to do. I’m in. He was trying to get me to switch rooms with Kevin or Dwight to be with him in a room.” Ryan shuddered as he said it. “Apparently he thought having a king bed was a selling point for switching rooms.”

Jim shot Pam his classic look, and they all started laughing. “Figured you might be. Michael might honestly kidnap you if you stay around him for too long.”

Ryan shrugged. “Yeah, I’m not exactly here to get kidnapped. I’d rather check out the actual city than stay trapped in some weird Disney bubble.”

Toby gave a quiet laugh. “Alright, then. Looks like we’ve got ourselves a crew. We’re officially ditching the dinner.”

Pam smiled, looking around at their little group but staying on Jim. “I think this is the best plan we’ve had all day.”

Chapter End Notes:
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