Tippy Doorman Dating Sim

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Harl paced in a tight circle around his apartment, trying to think. He hadn't actually dated anyone before, though he had crushes on people from afar, and despite all he did to help people with their romantic lives, he wasn't sure how to handle his own.

"I dunno," he said out loud. "I think helpful Harl Hubbs… needs help of his own."

He sighed, then brightened up. He could ask for help on his rounds today, while he was helping everyone else! That was a great idea!

Harl quickly gathered his things and headed out of his apartment. Once on his cart, he paused to think about where he was going first. He should someone he already knew, right? Probably another guy, because he was a guy, too.

An answer came to him. He grinned and started pedaling.


Harl pulled up outside the fire station. "Good morning, Buster!" he said, waving to the person standing outside. "Do you need any help?"

Buster rapidly shook his head.

"Okay," Harl said. "Could you tell Bob and Clemmons I'm here? I want to talk to them!"

Buster grinned and went inside. Harl waited anxiously on his cart for a few minutes before Bob and Clemmons came back out.

"Hi, Harl!" Clemmons said with a wave. "You wanted to talk to us?"

"Yeah!" Harl got off his cart. "I, uh, need some advice."

Bob raised an eyebrow. "Advice about what?"

Harl attempted a smile. "Dating," he said. "You're the only guys I know who are dating each other, and I want to date a guy, but I've never dated before, so…"

Clemmons gasped and clapped his hands to his mouth. "You have a crush?!"

Harl winced. "It's not that shocking, is it?"

"No, no!" Clemmons took his hands away, revealing a smile. "I was just surprised! We can help you, don't worry! Right, Bob?"

"Uh, okay," Bob said. "What do you need help with?"

Harl relaxed. "I dunno. Kind of everything. I mean, we've talked sometimes, but I don't know if he likes me, and I don't know how to get closer to him…"

"Not to be a downer," Bob said, "but do you know if he likes men?"

"Yeah! He's mentioned a boyfriend to me before. Ex-boyfriend, I mean. I think he's single."

Bob nodded. "Then it's time to teach you the art of wooing another guy."

Harl beamed. "Great! What do I do?"

Bob and Clemmons started firing off pieces of advice in rapid succession.

"You should give him flowers!" Clemmons said.

"Try asking him if he's interested in meeting for lunch," Bob suggested.

"You could watch a movie together? Dinner and a movie?" Clemmons frowned. "Do people still do that, or am I just old?"

"You might want to get to know each other before asking him out, but it's hard to do that if you're not already friends."

"Oh! Put yourself in life-threatening peril and then have him save you!"

Bob quickly covered Clemmons' mouth. "Do not do that," he said to Harl. "Just figure out what he likes, and try to talk to him about it. Maybe you'll figure out some way to impress him, y'know?"

Harl frowned. "I'm not sure what he's impressed by. Maybe…"

Actually, now that he thought of it, Tippy did think the Master Criminal was cool. After the masked villain had been outed as the person sabotaging the Mars Mission, Gabby had interviewed Tippy about it, as one of the contestants who was disqualified. "I don't know who the Master Criminal is," he said on TV, "but he must be very clever to not have been caught for so long. He probably also has muscles."

"Really!" Gabby said, holding the microphone uncomfortably close to Tippy's mouth. "What makes you say that?"

Tippy leaned away. "W–well, he does those parkour tricks, right? Flips and falls and whatnot. He's probably a master of acrobatics as well as crime, hah!"

Harl grinned. "Okay! I know what I have to do!"

"It's not the life-threatening peril one, is it?" Bob asked.

"Yeah," Clemmons said, "that was probably bad advice on my part."

"Don't worry," Harl said. "I know a lot of parkour, so I'll be fine. See you later! Thanks for the advice!"

He went back to his cart and drove away. Bob and Clemmons exchanged a nervous look.

"Should we be worried?" Clemmons said, his voice already tinged with worry.

"I don't think so," Bob said. "Harl can take care of himself, right?"

He gave Clemmons a kiss on the cheek. "I don't know," Clemmons said. "I think we should keep an eye on him, just in case."


Harl managed to get to the roof of Tippy's building by scaling the back, where the doorman wasn't watching. He took off his suction-cup shoes and went to the edge, squinting down at the street below.

This was a great idea! He had done parkour before, he could probably make it down to the street without breaking a bone or dying. Then Tippy would be impressed, and Harl could tell him about cool things people with muscles did, like eating healthy and working out.

He furrowed his brow. He didn't see Tippy's red uniform at the door. He got down on his knees and leaned forward over the edge to see–

"Harl Hubbs?"

Harl yelped and lost his balance.

A hand grabbed the back of his shirt, saving him from falling over the edge. Slowly, he was dragged back onto the rooftop, where he got his feet underneath him and turned to face the masked visage of his rescuer.

The Master Criminal narrowed his eyes. "What are you doing here?" he demanded in his gruff voice.

Harl laughed nervously and rubbed the back of his head. "Uh," he said, "it's kind of silly… wow, it's really you, huh?"

He tried to say it in a friendly way, but the Master Criminal flinched. "Really who?"

"The guy everyone's been talking about! I mean, I don't know who you really are, but you did a lot of illegal stuff, right? But, uh, you also just saved my life, so… thank you?"

"You're welcome," the Master Criminal said. "Now would you please answer my question?"

"Oh, right. I was trying to impress Tippy."

His face grew hot the moment the name left his mouth. Why had he said that? The Master Criminal was a complete stranger, he didn't need to know about Harl's crush! Harl stood there with his cheeks red, averting his eyes from the Master Criminal's reaction.

"Tippy Doorman?"

Harl wanted to run away and hide, but jumping off the roof wasn't really an option. "Yeah."

The Master Criminal made a small noise, then said, "Why were you trying to impress him?"

"Well, after he wasn't picked for the Mars Mission, he's seemed pretty down, y'know? And I like him, so I wanted to help, but…" Harl hesitated. "I know what people think about me. I don't want to get the situation Harl'd."

"I don't see how impressing him would help with that."

"It's not…" Harl twisted his hands together. "I want to help him a lot, I guess. I want to be around him, and be there for him, and… be *together* with him. I want to date him, but…" He sighed. "He's such a cool guy, and I'm just the guy who ruins everyone's days."

The Master Criminal said nothing. Harl managed a smile. "Thanks for saving me," he said. "I'll go now."

Just as he stepped around him, the Master Criminal put a hand on his shoulder. "Wait, Harl."

Harl froze. "Yeah?" he squeaked.

"You don't…" The Master Criminal paused. "You don't ruin everyone's day. I heard you were a great help with the Mars mission."

"Not really," Harl said. "Dr. Wexler said I was an annoyance and that he wanted me out of the way. Dr. Ravenhurst was nicer, but…"

"Still. It's admirable that you want to help everyone." The Master Criminal tightened his grip for a moment, then took his hand away. "Not everyone wants to create a better world. Some people just want to have power."

"Like you?"

"I–what?" The Master Criminal sputtered for a moment before regaining his composure. "I am doing what's best for everyone," he said, "whether they know it or not. I'm fine with working in the shadows and being hated by those who don't know better."

"Oh," Harl said. "I thought since you stole a bunch of stuff, you just wanted money or whatever. Sorry."

"Oh, no, my goal is far more noble than that." The Master Criminal sighed. "But it's fine if you don't understand. I just wanted you to know that you're not alone in wanting to help others and being shunned for it."

Harl stared at him with a small frown. The Master Criminal turned his head away. "Now get off this roof," he said. "I don't want you–oof!"

Harl hugged him tight. "Thank you," he said. "That… means a lot to me."

The Master Criminal gave Harl a few awkward pats on the back and pulled away. "You're welcome," he said. "But really, you should leave."

"Okay!" Harl said. "See you later, em-cee!"

"What?"

Harl was already opening the stairwell door and running down the stairs.

It wasn't until later that he remembered his suction-cup shoes.


His suction-cup shoes weren't on the roof the next time Harl went up there. They weren't in the building's lost-and-found either. Harl thanked the receptionist and left before Tippy's shift started.

Maybe the Master Criminal knew where they were? But that would mean Harl had to find him again. He sighed and got off his cart to sit on a bench in the park. He liked his suction-cup shoes.

"Heya, Harl."

He jerked his head up. "Hi, Officer Detain!" he said, smiling up at Duke. "Is there anything I can help you with?"

Duke shrugged. "Not really. I got a call that you were up on a roof, but you were gone when I got there, so I just wanted to check in."

Harl's cheeks flushed. "Oh, I was gonna do parkour, but I almost fell off the roof, so I didn't. I'm fine."

"Alright. Be careful out there; I don't want anyone getting hurt."

"Don't worry, the Master Criminal saved me."

Duke's eyebrows shot up. "Sorry, who saved you?"

"Oh!" Harl tried to laugh it off. "He wasn't doing any crimes or anything, he was just… on the roof for some reason. And then he saved me from falling."

"Still, if he was spotted there, I should investigate." Duke took out his car keys. "Thanks for the info, Harl. I gotta run."

"Wait!" Harl jumped up. "I'll come with you! You, uh, might need more info, right?"

Duke paused. "I mean, I appreciate the offer, but I don't think…"

"I want to help!" Harl protested. Well, really, he didn't want the Master Criminal to get caught after he saved Harl's life. He'd figure out some way to "Harl" Duke's investigation.

He could tell Duke was weighing the options. Finally, he relented. "Alright," Duke said, "just… try not to get in the way, alright?"

Harl beamed. "Don't worry, I won't!"


After the car ride there, Harl was questioning his resolve, but even with Duke's driving, they made it to the building Tippy worked at without him losing his lunch. Harl's heart jumped when he saw Tippy standing outside the entrance.

"Good afternoon, Officer Detain!" Tippy said brightly. "And… Harl Hubbs? What brings the two of you here?"

"We're here to investigate the roof," Duke said. "Apparently Harl met the Master Criminal there."

Harl laughed nervously. "Kind of? He just… saved me from falling and left. I mean, I left. I don't know where he went."

"I see." Tippy stepped towards them. "Allow me to be of assistance," he said. "I know this building inside and out. If the Master Criminal is here, I'm your best bet at tracking him down."

Duke nodded. "Fine with me. Lead the way, Tippy."

Tippy smiled and opened the door for them both, gesturing inwards. Harl tried not to look at Tippy as he entered and hoped his blush wasn't visible.

Tippy shut the door behind them and the group made their way to the roof.

When they emerged from the stairwell, the sun was creeping its way across the sky. Harl wiped his forehead. "This is where I met him," he said. "Uh… not much else happened, really."

Duke looked around. "Hm. Doesn't look like he left anything behind…"

Tippy nodded. "How do you think he got up here?"

"I dunno," Harl said. "He was just here when I turned around."

"Maybe he's hiding something up here?" Duke didn't sound convinced. "Or maybe he lives in this building?"

"Doubtful," Tippy said. "I know everyone in this building, and I guarantee you none of them are the criminal sort."

Duke sighed. "Maybe this was pointless," he said. "Maybe I should give up."

Tippy patted his shoulder. "You're awfully focused on catching the Master Criminal," he said. "May I ask why?"

"I feel responsible for what happened in the Mars mission competition," Duke said. "I mean, you were there, Tippy. You saw what happened! Gabby got a concussion, you nearly fell from a building… I'm glad Allen avoided those peas, otherwise he might've had an allergic reaction and been disqualified."

"Right," Tippy said. "Good for him. I wonder how he's doing up in space?"

Duke cracked a smile. "Bitter about not being chosen, huh?"

"Nothing so uncouth." Tippy turned away. "Though I will say, I was… disappointed when I heard the news."

"I can tell," Harl said. "You've been all mopey ever since the rocket launched. Is there anything I can do to help?"

Tippy glanced at him briefly. "It may be out of your hands too, Harl, but… I appreciate the offer."

Harl beamed. Tippy appreciated him! That was almost as good as impressing him, right? "Not a problem!" he said brightly. "Do you want to see me do parkour?"

"Excuse me?"

Duke stopped him before he got to the edge of the roof. "Maybe another time," he said, leading Harl away by the shoulder. "And a couple hundred feet closer to the ground. I think we've done all the investigating we can."

Harl nodded. "Alright," he said. "It was nice seeing you, Tippy."

Tippy smiled back. "Same to you, Harl."


That night, there was a knock on his window.

At first, Harl pressed a pillow over his head and tried to ignore it. Probably a bird or something. But the knocking continued, in patterns of sound that were clearly thought out, and he sat up and squinted in the darkness of his bedroom. "Hello?" he called out–no need to be quiet, when he was the only one in his apartment. "Who's there?"

The knocking continued. Harl got up and crept into the next room, where the window was.

The Master Criminal waved at him.

Harl squeaked and clapped his hands over his mouth. "What are you doing here?" he whispered. "Why are you doing here? I mean, uh–"

"Are you going to open the window or not?"

Harl unlatched the window and let him in. The Master Criminal looked around his apartment, his expression unreadable, then focused on Harl.

"There's something we need to talk about," he said.

"There is?" Harl said. "I mean…"

"You told the police you saw me, didn't you?"

The Master Criminal's voice was low and dangerous. Harl's gut twisted. "I didn't really mean to," he said. "I was just talking to Duke, and it just… slipped out. I'm sorry."

"You're sorry?"

"You saved my life, and then I got you investigated, sort of." Harl attempted a smile. "That's not very helpful of me, is it?"

Silence passed between them. The Master Criminal looked around the apartment again. "I'm surprised," he said quietly. "It's not often that I'm surprised."

"Huh?"

"Harl, maybe you've noticed, but people in the city are…" The Master Criminal waved a hand in the air. "…predictable. They do the same things, over and over, following their own wants and needs. You… don't do that."

Harl tilted his head. "I don't? I mean, I go out every day, helping people–"

"Exactly. You help others. Try to, anyway. Even when you have desires of your own, you frame it as helping others." He coughed. "Your attraction, for example."

Harl's face flushed. The Master Criminal continued. "You described your feelings as you wanting to help Tippy. Certainly, part of that is your own desire to date him, but… other people want things from relationships. They want to take something the other person has."

"Really?" Harl said. "That's not how it goes in movies."

"Movies aren't an accurate reflection of real life, but that's beside the point." The Master Criminal shook his head. "I don't understand you, Harl Hubbs."

Harl laughed nervously. "I don't really understand you, either. Like, why are you in my house?"

"Oh, I was going to convince you not to tell the police anything more about me, but it seems I misjudged your intentions. Now that I'm here…"

The Master Criminal sat down and took off his shoes. Harl stared in confusion before he recognized them. "Hey! Those are my suction-cup shoes!"

"I wasn't going to give them back," the Master Criminal said, "but, well, I think I ought to. They're certainly useful, though."

Harl picked them up. They had been stuffed with newspaper; the Master Criminal's feet were probably smaller than his own. "I can make you some," he said. "I made these ones myself, so…"

"Really?" It was hard to tell under the mask and bandana, but Harl thought the Master Criminal was smiling. "That's kind of you."

"Yeah! You helped me to, uh, not die, so I should help you, too. Right?" Harl smiled. "That's what I do, after all."

"Then we'll meet again, Harl Hubbs. I daresay I can help you with your problem as well."

"Huh?"

The Master Criminal took a step closer and pulled down his bandana. Harl didn't have a chance to react before their lips met. It took a moment longer to realize the Master Criminal was kissing him.

By the time he realized, the Master Criminal had pulled away. Harl could see his smile for real, now. "Sorry," he said. "I'll see you around."

"Uh," Harl squeaked, his cheeks flushed.

The Master Criminal repositioned his bandana and climbed back out the window. Harl leaned out and watched him jump from handhold to handhold until he was on the ground, where he disappeared into the shadows.

Harl touched his mouth, his heart pounding.

"Wow," he said.

But something wasn't right.

"I don't think he's going to help me be with Tippy…"

THE END

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