Disclaimer: I do not own Digimon or any of its characters. This is a nonprofit, fan-based story. Please support the official release.


The Chaperone

Terriermon took pride in how rarely he found himself at a loss for words. He acknowledged that this talent could be a double-edged sword at times, in that words would occasionally come to him in such large numbers that he had difficulty choosing between them. One of these scenarios was currently playing out right before his eyes.

It reached a point where Terriermon was pretty sure that Henry had forgotten he was in the room, too busy digging through the clothes in his closet to notice or care. Terriermon didn't let this bother him though, mostly because he knew why his partner was acting this way. Still, he felt like he had bided his time long enough.

"So..."

"Not now, Terriermon," Henry said instantly, apparently having not completely forgotten about the Digimon in the room.

Terriermon grinned. "I was just gonna say that I can help you."

Henry turned to face him. "No offense, but you're not exactly known for your dress sense."

"Rude," Terriermon grumbled. It wasn't his fault most manufacturers didn't make their clothing with Digimon in mind.

Before he could reply in any other way, Henry grabbed a shirt and pair of pants and left the room, almost bumping into Suzie and Lopmon on the way out.

"What's wrong with him?" Suzie asked.

"He's got a date," Terriermon answered proudly.

"It's not a date," Henry called from the bathroom. "Or at least I don't want to assume it is," he added, low enough that Terriermon might have missed it if not for his heightened sense of hearing.

"I don't know why not." Terriermon spoke loudly to make sure his partner heard him. "Alice very specifically asked if you were free tonight."

"So she ended up asking him out?" Suzie asked, not much surprise in her voice.

"Don't think she minded much, though," Terriermon replied in a sing-song voice. "She strikes me as the kind of girl who likes cracking the whip."

"Terriermon..." Henry warned as he reentered the room, having not changed his clothes while he was gone.

"What? She's not even here right now."

"Wouldn't talking about someone behind their back still qualify as rude?" Lopmon asked.

"Yes, Lopmon, it would." Henry looked from her to Terriermon.

"Did I miss the fun police handing out badges?" Terriermon asked with the hopes of getting a genuine answer.

"So, basically, you don't want to overdress?" Suzie cut in before he got one.

Henry slowly turned to face her. "Basically..."

"I see..." Suzie placed a finger on her chin.

"You have thoughts?" Henry asked with all the enthusiasm one could expect from a sixteen year old having to ask his younger sister for dating advice.

"Where are you going?"

"To a movie."

"What movie?"

"We haven't decided yet."

"How late will you be staying out?"

Henry raised an eyebrow. "Are you interrogating me?"

"Yes," Suzie answered without skipping a beat.

"Why?"

Suzie put on a playful smile. "Because I want you to remember how annoying it is to have an overbearing older sibling in this situation."

Henry sighed. "You don't have any actual advice, do you?"

"You know that I'm eleven, right?"

"Which is why you need help from a professional!" Terriermon quickly pointed out, not wanting to miss an opportunity to reinsert himself into the conversation.

Henry pinched the bridge of his nose. "For the last time, spending a week going through Jaarin's DVD collection doesn't make you some kind of love doctor."

"C'mon, Henry!" Terriermon couldn't figure out why his partner was being so difficult. "Just ask Takato how great a wingmon I am. I helped him win his dream girl, didn't I?"

"I have a feeling that any progress Takato and Rika have made has been despite you."

Terriermon crossed his arms. "Okay, now you're just being mean."

"May I make a suggestion?" Lopmon asked suddenly, silencing everyone.

"Sure," Henry answered.

Lopmon took a second, looking between the various faces in the room as though she were having second thoughts. "I won't pretend to know about human courtship, but even if Alice is only looking for friendship, she's doing so because she likes you as a person. Perhaps all this overthinking defeats the purpose of that?"

Suzie eyed her partner closely. "That's a pretty long-winded way of saying 'be yourself', Lop."

"Sorry..."

"You know what? Don't be." Henry dropped the clothes in his hands on his bed. "Thanks, Lopmon, I'm gonna do that."

With that, Henry left the room, not even waiting to hear Terriermon's thoughts on the advice he had just been given. The room went quiet after that, at least until they heard Henry leave the apartment and close the door behind him.

"How long a head start are you gonna give him?" Suzie asked, as though she knew exactly what Terriermon was getting ready to do.

"Just long enough for him to get to the lobby," he answered. "These legs weren't built for running."

"You're going to follow him?" Lopmon asked with genuine confusion.

"Duh."

"Don't you think he'd want some privacy?"

Terriermon didn't give an immediate response, not really understanding the intention behind the question. He looked to Suzie for clarification, but all he got from her was a shrug. He ended up throwing the thought out, deciding it was wasting his time.

"Alright, I'm off," Terriermon declared as he moved for the door.

"Make sure you bring back something I can hold over him!" Suzie called after him as he rounded a corner.

Making his way to the Wong's fire escape, Terriermon paused to survey the street below. After spotting Henry, he dove off the building, outstretching his ears so that he could glide safely to the ground. He had little trouble keeping pace with his partner after that, a sign that Henry was nervous and that Terriermon was going exactly where he needed to be.


The movie Henry and Alice had ended up choosing was uneventful. While this disappointed Terriermon a bit, it didn't surprise him, given how humans tended to look at talking during a screening as some kind of taboo. What actually surprised him and worried him just as much was how that trend continued after they left the theater.

Terriermon carefully followed the two teens as they walked the city streets, just closely enough that he could hear them when they spoke. Not that it really made a difference at the moment.

"So..." Henry began. "Did you like the movie?"

Alice glanced at him and shrugged. "It was okay."

"Right..." Henry replied before silence followed. Again.

Sheesh, Terriermon thought as he scurried up a nearby tree. At least when Takato gets nervous he can't stop running his mouth.

Eventually they came to an American style diner, entering and picking a booth with barely a couple words shared between each other. They dropped their coats on the seats before Alice gestured towards the bathrooms and walked away. Henry sat down, leaning forward with his brow wrinkled, which was what he typically did when he was in front of his computer trying to solve a problem.

The coast now as clear as it was going to get, Terriermon darted towards the diner, moving inside and only stopping once he was standing on the table right in front of his partner and looking him in the eye.

"What are you doing over here?" Terriermon questioned, trying his best not to draw too much attention to their booth.

"T-Terriermon?" Henry's eyes went wide with genuine surprise.

"Don't you 'Terriermon' me. Now answer the question."

"I'm... not doing anything."

"Exactly!" Terriermon jabbed a pointed finger in his partner's face. "I thought you were just gonna be yourself."

Henry crossed his arms. "How am I not doing that?"

"You're being all..." Terriermon took a second to look at his partner and try to figure out the right word. "...polite, and not the normal kind of polite you are on your own. It's like you're holding back."

Henry looked away for a brief second. "Okay, maybe a little, but I don't want to start an argument."

"Why not?" Terriermon glanced in the direction Alice had left in. "Isn't that what the two of you do?"

No sooner had he finished the thought that a light bulb turned on in Terriermon's head. He had an idea, if not the solution to Henry's problem.

"Terriermon-"

"Make her mad."

Henry raised an eyebrow "What?"

"You heard me." Terriermon gestured to where Alice would be sitting had she been present. "Antagonize her. Trigger her. Get a reaction."

"Why would I do that?" Henry asked, not trying to hide how skeptical he was.

"Because you like this girl."

"And how is insulting her going to help?"

"I didn't say anything about insulting her," Terriermon clarified, a little annoyed by how he had to explain everything. "You worked together all that time, so you have to know what gets her talking."

Henry paused, as he often did when considering something he had just heard. "Even if, how do I know this won't make things worse?"

Terriermon couldn't give a straight answer, as not everyone had his sense of tact. Still, Henry's question meant he was willing to give the idea a chance. All he really needed was one more push.

"I bet you it won't," Terriermon said, placing his fists on his hips as he spoke.

"What?" Henry asked, confused again.

"And if I'm wrong, I won't tell anyone what a dead fish you've been, and I'll stay out of your personal business from now on."

"You should be doing that anyway," Henry growled.

"I didn't hear a no," Terriermon sang.

Henry shook his head. "And what do you want if you end up being right?"

That was the question of the day. He thought about it for a second, but only one reward seemed appropriate given the situation.

Terriermon smiled. "You have admit that I'm the best wingmon a Tamer could ask for."

"You're not gonna rest until I use the word, are you?" Henry asked wearily.

"Moumantai, Henry," Terriermon reassured his partner. "You can wait til we're home to say it."

"You're so gracious," Henry mumbled.

Terriermon pointed at one of the diner's menus. "I also want hash browns."

"Do you even know what hash browns are?"

"They look fried and not very good for you, so that's good enough for me."

Unfortunately, that was where their conversation would have to come to an end. Terriermon could just make out the sound of a door opening, which signaled that he would have to make himself scarce.

"Sorry, gotta disappear!" Terriermon considered leaving the diner entirely, but instead settled for simply jumping off the table and into the seat next to Henry. With the same motion, he also threw the boy's coat over himself.

"Terriermon!" Henry hissed.

"Shush!" he whispered back. "You'll give me away."

"She's not going to fall for-!"

"Are you okay?" Alice's voice suddenly cut in.

"Y-Yeah..." Henry replied nervously. "I was just, uh... I'm fine."

"Alright..." Terriermon heard the girl sit down as she spoke.

"So, you know what you're gonna get?" Henry asked.

"Yes," Alice answered, though the silence that followed confirmed she wasn't going to elaborate.

Said silence continued for a little bit after that, with it finally being broken by Henry letting off a quiet sigh.

"So..." Henry began, sounding a little reluctant for Terriermon's taste. "I uploaded that patch you wrote for the D-Chat."

Alice waited a heartbeat before answering. "And?"

"We're still getting the same error message."

"Then you messed up the application of it," Alice explained, a hint of irritation in her voice.

"I don't think so," Henry replied, though his voice actually sounded a little lighter if anything.

"Well, that's obviously what happened."

"Are you sure you didn't make a mistake?"

Alice paused again. "Positive."

"Then I'm stumped," Henry responded, probably with a smile on his face if Terriermon had to guess.

"Do you remember what you did exactly?"

"Parts of it. Do you really think you can figure out what went wrong right here?"

"That's the plan," Alice answered over the sound of a napkin dispenser being emptied. "Excuse me, do you have an extra pen?"

"Sure..." came the confused reply of a nearby waitress. "Are you guys ready to order?"

"The deluxe cheeseburger, hold the onions, please."

"I'll have the same, just minus the cheese," Henry added before pausing for a second. "And... an extra side order of hash browns, please."

The waitress quickly repeated their order before walking away. There was silence again between the two teens, but luckily, it didn't last.

Alice sighed. "Terriermon can come out as long as he stays quiet while we work."

Terriermon instantly threw Henry's coat off of him. "Hey, once the food gets here, you won't hear a word from me!"

"You knew?" Henry asked, looking between the booth's other two occupants.

"He's been following us since the movie theater," Alice replied before pointing her pen in Terriermon's direction. "For the record, you are not invited next time."

"Whatever you say," Terriermon said innocently, which earned him a sideways glance from Henry, who likely knew the words were empty. Not that he could ever make that promise in good conscience.

After all, if he did he wouldn't be able to call himself the best wingmon in two worlds.