Me and my sister had an hour-long conversation about this, and it was too good not to write down and share. Much help from said sister, shadeslayerprincess111. (Also partially inspired by the toursies and from some tumblr hc's!)

Please review!

...

Santa Fe.

It was perfect. What else would you do if you won the lottery?

Well, other people probably did lots of other stuff, but Jack was going on a road trip to Santa Fe. And he was taking Katherine. Maybe Crutchie too, since Jack would never leave him behind. Katherine wouldn't mind. What else would he do with 20,000 dollars?

Only it didn't turn out quite as planned.


They only had the van. The stupid 12-passenger van with too many roll-down windows and a really weird shade for the interior, and no cup holders. Jack figured the three of them could always sleep in the back.

Well, five of them. Davey and Les were coming too. He couldn't very well just leave Davey behind, and since he was in charge of babysitting Les, the kid was coming too.

Jack didn't have another car, and besides, he kind of liked his van. Even if it didn't have cup holders. And gigantic vans were great for road trips.

They had maps, they had snacks, they had blankets and pillows and plenty of room, and they even had camping equipment. Spot Conlon wouldn't be in a 100 mile radius in about an hour. It was quiet. No one even complained when Jack made them meet up at 6 am to get an early start. Katherine called shotgun first, Crutchie got in the back to get more sleep.

Jack was just checking the tires one last time when they showed up.

"Hey, guys, he hasn't left yet!"

Jack whirled around just in time to see Race and Albert, the latter dropping an entire armful of stuff and plowing forward towards the passenger seat. "SHOTGUN!"

"Wh—"

"Jack, we're not late, are we?" a voice piped up at his side, and Jack suddenly realized that his road trip was dissolving before his eyes.

"Uhh, Romeo, what are you guys doing here?"

Albert had got to the passenger seat first by knocking Race over, and had yanked open the door only to find Katherine already in his claimed spot.

"Ya idiot, what do you think we're doing here?" Specs (he was here too?) joked, slapping Jack on the back. "We're going to California, right? Looks like you got plenty of room."

"California?" Jack squeaked out.

Specs nodded enthusiastically, Romeo grinning next to him.

"I've never been out of New York!" Elmer's voice materialized from behind him.

"Me neither!" Jojo said, joining the group by dragging over a very large suitcase.

"They're coming with us? Cool!" Les yelled from the van, and started towards the group, followed by Davey.

Jack turned back to the other boys, realizing that Henry, Buttons and Finch had come along to.

"You're coming with us?" Jack echoed, realizing that he had done nothing but repeat everything for the last five minutes.

"'Course we are, Jack! You won't have no fun unless we do!" Race said, putting his arm around Jack's shoulders. "Besides, I think your car's going to be a little empty unless you do."

Katherine had come over too. "I didn't know the boys were coming with us."

Jack shrugged, "I didn't either," he managed in a very small voice. He couldn't just tell them they couldn't come, and even if he could, Jack doubted that it would matter. It wasn't that he hadn't wanted them to come; it was just that he'd ruled it out immediately based on the fact that he liked living and he was pretty sure that everyone else did too.

He looked at Katherine, she shrugged. He didn't know what a shrug meant. It was either "Jack get a backbone and say no" or "the more the merrier." Les was jumping up and down with excitement; Davey was getting lots of back-slapping in the form of greetings. Crutchie was still asleep. No help from any of them.

He'd wanted a nice, quiet trip. Besides, there wasn't enough room for all of them. The rest of the boys were looking up expectantly. Jack cleared his throat. "Sorry, fellas, but-"

Les gasped, "No, Jack, I want them to come!"

Race actually looked sad, Romeo and Buttons looked on the verge of tears, and Finch's shoulders were drooping.

How bad could it be? They were his friends. Jack didn't think he could tell them no.

"But there's more of us than there are seats," he finished.

Nine faces lit up. "Does that mean we can come?" Elmer asked.

"Yeah, what the heck. What's the worst that could happen?" The boys and Les broke out into cheering.

He dared a quick look at Katherine, she didn't look mad. He must've interpreted the shrug correctly.

Albert shoved Race aside again and made a dart for the van, screaming "Shotgun!"

"Hey, wait a minute, stop!" He grabbed the back of Albert's shirt, keeping him back. If he was getting nine new traveling companions, there had to be order.

"Aw, Jack," Albert started, but Jack shut him up.

"Ground rules. Number one, Katherine gets shotgun the whole time." Albert looked ready to protest, so Jack quickly continued, "Number two, no pushing each other or fighting or violence. Number three, seatbelts on. The whole time. And four, you guys gotta clean the car up at the end of the day. And five, windows stay rolled up unless I say so, and no screaming or distracting me. And no smoking." He directed the last one at Race. "Or I take the cigars."

He was immediately met with agreement "Sure, Jack, we can do that," and "You got it, Jackie."

They headed towards the van, all the boys hauling luggage. (Except Elmer, who didn't have anything with him?) Henry opened the door, started to claim the back row.

"Hey, Crutchie's here too! Hiya Crutch!"

Jack remembered Crutchie a second too late. He must've fallen asleep.

"What are you guys doing here? WHAT IS GOING ON?" his friend, now awake, yelled, and Jack could only shrug again.

"I thought it might be more fun to have the whole crew along. What's the worst that could happen?"

"Oh, hey, me an' Race can sit in the trunk, that'll solve the problem!" Albert yelled, a little too excited to be quiet.

"The trunk?" Katherine, Davey and Jack said in unison.

"Yeah, like where the luggage goes! Where'd you expect us to go, the roof? That's for the luggage!"

Before Jack could say anything, Specs threw him an armload of tie-down straps and bungee cords.


An hour later, with all of their luggage and the camping equipment—minus Jojo's very large suitcase that he insisted had to go in the trunk with Race and Albert—strapped to the roof and everyone buckled in, they were off.

There was a lot of initial hysterical screaming and yelling for about five minutes, someone was playing "Holiday Road" from tinny phone speakers and someone else was yelling the lyrics to "Here I Go Again," and Jack tried very hard not to regret his decision to let them come along.

But then everyone got surprisingly quiet. Jack had strategically place the quietest boys in the front row behind him and Katherine—Davey, Les, Crutchie. The rest of them were in the back two rows. He could hear Albert and Race laughing manically from the trunk, and was glad that he couldn't actually see what they were doing.

By the time they'd gotten out of Manhattan, it was actually sort of quiet. Jack sneaked a glance in the review mirror, most everyone was asleep. In the back row, Romeo had forgone the middle seat and was instead sprawled on top of Henry, Elmer and Jojo's laps.

"This might not actually be so bad," he said to Katherine. She had three different maps and an entire collection of pens and highlighters and was trying to give him directions. "They can act like relatively docile sometimes. And," he gestured to the open space between them on the bench seat. "If anyone misbehaves, they can sit in the time-out seat. That should keep them in line until they find out that we're actually going to Santa Fe and not California."

"We did talk about going to San Francisco. We could go to Santa Fe on the way there," she suggested.

"I guess we'd by two-thirds of the way there if we were in New Mexico." Jack thought about that. "The Great American Road Trip! From the Atlantic to the Pacific!"

He poked her. "Find me a route, Ace. If we're going to haul the whole gang across the county, we're going to do it right. California it is!"

Katherine threw one of her pens at him, giggling. "And turn the radio on," Jack continued. "Can't have no road trip without tunes."
As it turned out, that was a mistake.

"Eye of the Tiger" was playing, and that woke everyone up because they had some unspoken rule that the song needed to be yelled along to. In the midst of the chaos, the sun came out and Jack practically resorted to sign language to get Katherine to get his sunglasses because talking and trying to be heard would be futile at this stage. He was pretty sure that someone was dancing in the back row, but it was kind of hard to tell because Race chose that moment to climb over the backrest from the trunk and sit on top of Henry in order to roll down the window. "SUN'S OUT, GUNS OUT!" he screamed, sticking his arm out of the window.

Jack's rules went out with it.


After Elmer asked, "What do you actually do on road trips" and Les had said, "Are we there yet?" three times, Jack decided it was time for a bathroom break. They'd been on the road for a few hours, and he pulled off at the next rest stop he saw.

The boys piled out of the car, Race and Albert vaulting over the top of the back row in order to get out. Buttons had been sleeping on the floor, and fell out when Finch opened the door. Jack got their attention before they scattered, "Ten minutes, tops. If you're not back, I leave without you."

Ten minutes later, he was the only one back at the van. He waited three minutes; there was no sign of any of them. Then Jack got worried, ran back inside only to find Buttons, Romeo and Davey each with about ten brochures from the display that had one for every tourist trap with a three-state radius. He found Albert, Henry, Jojo and Finch still in the bathroom, playing with the automatic sinks.

The rest of the crew was by the vending machines, watching Race violently trying to get his stuck soda out by attacking the soda machine. Jack interfered before the whole thing could tip over on top of them. He grabbed the back of Race's shirt and dragged him away.

Thirty minutes after they initially stopped, they were back on the road. They were now in New Jersey, and Jojo very helpfully pointed out a field of cows.

Katherine swiped the aux cord from Crutchie, and both of them and Les started singing Disney songs. Jack was also surprised that apparently he was the only one that didn't know all of the words to "A Dream is A Wish Your Heart Makes," after every other occupant of the van sang along to that one. Halfway through, he swore that he could hear what sounded like Spot Conlon singing, too. Jack shook his head. Maybe he was starting to crack.

Ten minutes after that, Specs yelled that he had to pee.

"We just stopped! Didn't you go then?" Jack yelled, ignoring Katherine's suggestion to silently count to ten before answering

"Well, I didn't have to go then!"

This time he did count to ten, took a deep breath, and managed to ground out, "I'll pull over in a minute and you can go in the woods."

"JACK, I CAN'T GO IN THE WOODS!"

Specs had to hold it.


Around noon, the boys started dropping hints that they were hungry. "Hey, guys, look! A Taco Bell!" Crutchie said, and the rest of them started out the window at the passing restaurant like it was the best thing they'd ever seen.

Also "Wow, I could really go for some food right now," from Albert, yelling to be heard from the back.

And, "Hey, look. Cows," from Jojo.

Jack took the next exit with a McDonald's. "Figure out what you want, guys, I'm going to hit the drive-thru and we're going to get back on the road."

"Awww, Jack, I don't want to go to McDonalds!" Finch said, pouting. "Can we at least go to Burger King? I got coupons."

"Finch, it's literally the same thing! I'm not going anywhere else," Jack said, using his best Mom voice.

As soon as a slowed down in front of the menu board, Specs bolted out of the car and made a beeline inside, presumably to the bathroom.

The rest of them started shouting out what they wanted. "Okay, one at a time!" Jack yelled, but that didn't work very well.

"Hey, Jack, can I get two number fives?" Race asked (he'd somehow managed to get out of the trunk).

"Oh, also get me some cookies," Romeo put in, even though he'd already had his turn. Les started to change his order, Davey shut him up.

"Supersize me!" Someone yelled from the back. It sounded weirdly like Spot Conlon. Jack shivered.

"You want two, Race?" he tried to clarify.

"Yeah, and Romeo wants his cookies. And Albert wants you to get him one of the breakfast thingies."

Specs jumped back in the van, holding a to-go bag. He then made Jack order him more fries since his immediately got stolen.

They ended up having to wait about twenty minutes for their food. And somehow, all of the boys from the backseat crowded into the front row. Romeo and Race ended up between him and Katherine, Romeo sitting on Race to lean over Jack to flirt with the cashier. Half the boys were basically out the windows, someone stole Spec's glasses. He could hear some muffled yelling, it sounded suspiciously like Henry screaming that he was drowning. Jack risked a glance behind him. They'd piled on top of each other in order to fit up front, and he thought he could see Henry at the bottom. Specs had taken refuge in the middle row, muttering that he now hated everyone and was going to spend the rest of the trip watching vines.

Katherine sent them all back to their seats when the food arrived. As everyone was passing around the bags and getting their food, Romeo shrieked from the back, "Jack, you forgot my cookies!"

Jack hadn't even realized that you could order cookies at McDonald's. "We have to go back through and get them!"

Romeo was really convincing when he wanted to be (dang puppy eyes!) and since he looked ready to cry, Jack got back in the drive-thru line. Which, thanks to how long it had taken them to order, was about 10 cars deep. They'd all finished eating before they even got to the window, and Romeo scrambled up front and took them from the window before Jack could even take his hand off the steering wheel. Jack considered adding an "all sales final" policy to the rules.

Back on the road somewhere in Pennsylvania, Specs had traded seats with Crutchie and was now sequestered in between Davey and Les. Headphones on, he was glued to his pone, "Look at all dem chickens!" Les repeated it while Davey looked up from reading War and Peace and glared at him.

Race broke the rules again within five minutes by attempting to illicitly smoke from the trunk. "I will turn this car around, Racetrack!" was Jack's response. However, his wrath got sidetracked when Elmer announced he had to pee, and everyone else agreed, and Jack had to pull over yet again.

While they were waiting for everyone else to get back, Katherine whispered to Jack that she'd taken all of Race's cigars, and giggling, they hid them under the driver's seat.

After ten minutes, Jack closed his eyes, crossed his fingers, and hoped he had everyone, and they got back on the road. Albert had gotten a hold of the aux cord, and was playing, "Never Gonna Give You Up," which, apparently, was hysterically funny.

"COWS!" Jojo screamed, overenthusiastically pointing out the window.

"Why you always lyyyyinnn'?" Specs said.

Jack's started phone started ringing, "Why is Crutchie calling me?"

Katherine yelled for everyone to be quiet, and turned it on speaker. "Hello?"

"HEY YOU GUYS LEFT ME AT THE REST STOP! HOW COULD YOU DO THIS TO ME?"

Jack's headache suddenly increased exponentially. And it was only the first day.