Being in the position that was Jon Stewart's wife meant that Tracey got to go to a lot of high end dwellings. She'd been to after parties and dinner socials in some of the most expensive outlets imaginable in the city...none of them were even as close to elegant as the Canterlot Castle.
Both Jon and Tracey assumed that Celestia would simply teleport them to the restaurant but as it turned out she used her magic to send them right in the middle of her throne room. She didn't want to pass up the opportunity to see Jon again since their first encounter, and indeed Tracey as well for the very first time.
Originally Celestia was hoping to escort them both personally to the city but as luck would have it she was called away on important business; just as well too since she didn't want to impose on them by acting as the third wheel. To further help them on their date night she set them up on a royal trolley ride that would eventually drop them off in Canterlot proper. They took a special trolley that was accessed from behind the castle to avoid being noticed.
In any other case It would be customary to have some royal guards on board with them but she felt it wasn't necessary since some we're already waiting for them down in the city. That and having burly guards hovering over them might've killed the moment.
"Wow." Tracey said.
"Is that a good 'wow' or a bad 'wow?'" Jon asked his wife who was busy enjoying the scenery. For miles she could see rolling green hills and the occasional mountain terrain. Below the trolley lied the Canterlot city and its many structures. She had positioned herself at the very edge of the moving container and had stuck her head out to get a better view while Jon stood in the center.
"It's...all so beautiful." She commented. "Not at all what I expected."
"What did you think this would be like?" Jon asked taking a seat nearby but not directly next to her.
"I don't know," she said. "I guess I sorta expected...decrepit buildings, dragons flying around and monsters running loose...but this...this just looks like...like..."
"Like something an 8-year-old girl might dream up?" He said.
"Exactly!" She exclaimed. "Thank god you never brought Maggie here; she'd never want to leave."
"Yeah well this place isn't all that great...for starters good luck finding an outlet or any forms of technology past the 1850's for that matter," he said, looking down at some of the buildings below him. "Also they seem to be very fond of the colors pink and purple...not that I know any better but I think these people need to find someone whose special talent is interior decorating."
"Cold." Tracey said.
"Oh, I didn't I was being that mean." Jon responded.
"No, I mean it's cold up here," she added. "If I knew we'd be spending so much time outside I would've brought a coat."
Jon looked back at his wife and noticed that she was shivering slightly and rubbing her hands against her arms. Immediately he sat next to her, took off his pea coat and draped it around her shoulders. He let his left arm hang around her to share some of his warmth as well as to try and get in close.
"Thanks," she said with a smile as she leaned back towards him. She turned her head again to look back outside at the horizon. "So...give me the grand tour."
"Alright...uh to our left we see the lovely Canterlot Castle, the dwelling place of Princess Celestia who is the leader of this world." Jon said, trying his best to remember all he knew about Equestria. He swung his hand over to the side to show his wife the cluster of clouds that was Cloudsdale which was spewing rainbows out of every orifice. "And to our right...we see a town that desperately needs a lesson in subtly."
Tracey laughed so hard she threw her head back, almost hitting Jon in the process. As redundant as it may sound she always found him funny; even when they first started dating. She was enjoying herself but mostly because she got to be alone with him.
"You know I expected this place to be different," she said. "I just didn't think it would be...this different."
"Don't worry," he assured her. "You get used to it."
"Oh really," she responded. "And what's your secret to dealing with all this?"
"Well if I told you then it wouldn't be a secret now would it?" He answered. Tracey lightly jabbed her husband in the stomach with her elbow then looked back outside.
"So...what's that town called?" She said pointing ahead of her.
"Oh that?" He said, squinting his eyes to get a better view in the dark. "That is the town of...Ponyville."
"Ponyville?" She laughed.
"I know right!" Jon said sharing a laugh with her.
"Have you ever been there?" She said. "To Ponyville I mean."
"Oh yes, yes, many times." He answered. "A lot of the guests I've had on the show live over there."
"And here in Canterlot?" She ventured further.
"The castle I've been to, yes," Jon said. "The city, no not really."
"And what about the rainbow city?" She asked pointing to direct his attention back over to Cloudsdale. "Ever been on business there?" Painful memories once again returned causing Jon to tense up, though it wasn't noticeable to Tracey.
"Uh, if it's all the same with you I'd rather not talk about work at the moment." He said trying to change the subject.
"Oh, yeah of course, what was I thinking?" She said sounding somewhat embarrassed. "Tonight let's just enjoy this time together away from...well everything." To emphasize her point she leaned in even closer to Jon. Their eyes met and all at once Jon felt like he was a kid again, taking some young girl out on a date to impress her. Feeling that the mood was right Jon leaned in to give his wife a kiss.
Feeling the same way Tracey did the same. Their lips almost touched when a bright light erupted from the other side of the Trolley momentarily blinding them both.
"GAH!" Jon yelped as rubbed his now eyes in futility. "What the hell!?"
The flash itself was not unlike what one would expect from a burst of magic so Jon looked around to see if someone had appeared. And since it was already dark out, the sudden exposure of light meant that their eyes struggled even harder to regain focus. Opening his eyes Jon could just barely make out the silhouette of a figure just outside of the trolley, before his vision was fully restored the figure in question disappeared.
"AH, son of a bitch!" He yelled. "What was that?!"
Both their visions eventually returned and there was no sign that anyone was in the trolley with them or that there had been at any point besides them. Jon gave a Tracey a confused look realizing that if he didn't know what was going on than neither would her.
"Must have been...uh, nothing...probably nothing?" Tracey said without confidence, her vision having mostly returned.
"Yeah that's what they say in the horror movies," he commented. "And then next thing you know BAM!"
Jon briefly got up to investigate before Tracey grabbed him by his hand and yanked him back down next to her.
"It's fine hon, don't worry about it," she said, still holding his hand. "Now then...where were we?"
This time it was Tracey who leaned in, obviously still in the mood. Jon obliged and inched his face closer to hers, ignoring what happened and trying to enjoy the moment. But again they were interrupted; not by anyone in particular but by the trolley which came to an abrupt halt. The stop was so sudden that Jon jolted forward, accidentally colliding his head into Tracey's. The mood was now officially broken.
The door to the trolley swung open and a booming voice got their attention.
"Esteemed guests!" An authoritative voice declared. "We have arrived in Canterlot."
With a sigh Jon helped his wife up and the two exited the enclosure. The first thing they saw wasn't whoever it was that greeted them but rather the city of bright lights just ahead of them. Centerlot at night was truly something to be seen; unlike Ponyville even at night it was till bustling with activity. It was the Equestrian city that never slept.
"Incredible." Tracey said. Her eyes were fixated on the massive city before them. To her it looked like all the best parts of New York had collided together in one brilliant metropolis. Even for a city boy like Jon who had seen it all, he found himself gawking at the wonder the Canterlot skyline.
"Ahem." the voice said to get their attention. Jon and Tracey looked down to see a pair of larger than average colts standing in their way; both of them unicorns. They were near identical with similar shades of white fur and matching gold armor.
"At the request of the Princess we will be acting as your royal escorts for the night." The one on the left said.
"Indeed." The other one added. "Our orders are to follow your demands and make sure you have a safe trip while in the city."
The two of them stared at their pony counterparts who in turn stared right back. Jon didn't exactly know how to proceed from here since up until now he'd never had royal guards act as his own personal tour guides; nor had he ever seen one from this world. Tracey on the other hand could hardly contain herself.
"Oh. My. Goodness!" She exclaimed. "Jon, honey look! Someone went and dressed these two ponies in adorable guard costumes! Ooooh aren't you two just the cutest little things ever!?"
Squatting down to match their level she began to scratch one under his chin. Both guards were noticeably uneasy by this kind of attention but neither of them spoke out against it. One reason for this was that they were instructed to do whatever they wanted without falter, and other reason being that the two humans were almost twice their size.
The sight of his wife making baby talk at two seemingly rugged guardsmen complete with spears and combat armor made him laugh to himself.
"Alright Trace I think...I think it's time we headed out now," Jon said trying to get his wife to stand back up. "You're making our royal friends here uncomfortable."
"Ok, ok, I'm sorry," She said. Reaching into her purse she grabbed a handful of trail mix she always kept in a baggie just in case. Extending her hand outward she presented it to them as a peace offering; they didn't accept it. Instead both of them turned around towards the city.
"If you are ready we will escort you to the restaurant." One of them said. Jon and Tracey nodded and the two began to follow them close behind.
Their present location was on the outskirts of the city, where trolleys docked and hardworking Earthponies congregated to work on the mechanics or transport cargo. Once they got into the heart of the city the mood changed, soon the couple were surrounded by similarly well-dressed ponies, mostly Unicorns, walking about and socializing. The transition between the two areas was so abrupt it was almost instantaneous.
The two guardsmen continued to escort with Jon and Tracey marveling at the scenery, occasionally catching a few glimpses of ponies doing the exact same about them. They got some looks of confusion and worry; for most this was their first time laying eyes on a human. Jon tried his best not to stand out but didn't take long for someone to make the identification.
"HEY!" A random citizen shouted. "THAT'S JON STEWART!"
Immediately a herd of ponies surrounded them, all wanting to say something. Celebrities were known to associate with each other within the walls of Canterlot but this was different. For the ponies of this town having a human celebrity in their presence was a once in a lifetime opportunity, none of them wanted to pass it up.
Both Jon and Tracey struggled to keep their balance as pony after pony fought to get their attention. The last time either of them were surrounded by this many small animals was when they took their kids to the petting zoo in Grand Central park. Before they could answer any of the dozens questions being tossed at them from all sides a large noise like an anvil falling down got everyone's attention. It was one of the guards slamming his heavy spear against the ground.
"CITIZENS!" He yelled. "We are here on an official assignment from the royal palace...if you do not wish to be cited I suggest you go about your business!" As commanded the multitude of pastel colored ponies fled in all direction; each of them pretending to be busy, but all eyes were still on Jon.
"Oh wow," Jon said. "Uh...thanks for the help..." Jon left his words floating in the hopes that the two guards would finish his sentence by revealing their names. However they simply walked forward on the way to the restaurant which wasn't yet in sight. In an attempt to get a conversation starter Jon tried to identify what their cutie marks were but their armor completely covered their flanks, making it impossible.
"So uh, how long have you two worked for the Princess?" Tracey asked to break the silence. Either they were purposely ignoring them or they were too focused on guiding the two tourists through the busy streets of the city; but for whatever reason they didn't answer back. As much as Jon appreciated Celestia wishing them safe passage through her backyard he couldn't but feel more like a prisoner than a guest of honor at this point.
"You guys sure are a talkative bunch, aren’t ya?” He jested. Again the two straight faced soldiers said nothing and continued doing what they were ordered to do.
As they continued to walk deeper and deeper into the city the citizens all around them kept to themselves but their gossiping was uncontrollable. Some of them even followed from far behind to see where they were going while other just gawked.
It seemed that the more they walked the taller the buildings became. Jon looked to his far left than his far right to get a good panoramic view of the city; he did the same again but this time he looked down then all the way up. The buildings were clean as was the streets which were large in seemingly endless. Jon could probably drop onto the floor and roll around and not even catch a speck of dirt on him.
Even for someone as famous as Jon this all felt very new. He wondered if his wife felt as uncomfortable as he did so to ease her potential suffering he reached out to her.
"So, you enjoying herself yet?" He asked Tracey as he places his arm around her waist.
"All things considering...yeah I am?" She answered with a smile. Before any of them could continue their conversation a bright light surrounded them, momentarily illuminating the entire area. It was the same flash of light as before in that it was so bright that it blinded them once again.
"UGH not again!" Jon grunted. "What is that!?" Before anyone could answer a voice from on high caught his attention.
"Great angle!" The voice shouted. "That one's going to be totally grasshoppa!"
When Jon's vision came back he looked above him to see what had caused the flash of light. It came from a Pegasus flying just above him with a camera around his neck.
Jon had never met him before but he could spot his kind a mile away. He was a paparazzi pony.