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Gregory: The Boss

  • wateryourcellphone
  • Jul 29, 2025
  • 12 min read

Updated: Jul 30, 2025

By Mia Huerta

189.9 million laptops were sold in the year 2024, and Jillian just so happened to buy the only one in the world capable of sassing her.


When she opened it up, emotionally prepared only for a functional laptop with the latest version of Windows and a touchpad that would actually work, hearing it speak was alarming, to say the least.


He made it clear immediately that his name is Gregory and that he is The Boss.


“Get up!” he would yell during those long Sundays where she stayed in bed a little (a lot) too long.


“Get to work!” he would chastise when she would take a minute checking her socials.


“You’re a pain in the ass! Have you ever heard of a work-life balance?” she would quip back.


“Have you? Cause you seem to do a whole lot of life.”


“One could say that’s better than doing a whole lot of work.”


“Not if your life consists of doomscrolling and sitting around in your bathrobe thinking of reading a book and then not reading a book and then getting mad at yourself for not reading a book.”


“That’s not all I do with my life! I hang out with people! I watch movies!”


“When’s the last time you’ve been on a date, Miss Asagiri Gen fangirl?”


“ExCUSE me! Even if I were to ask someone out, I feel like an extra roommate named Gregory would be a pretty big turn-off!” She has gotten up now, pointing at the machine as though she’s a witch about to curse him.


He has no eyes to roll but she can imagine it perfectly. “You’ve got a deadline in five hours. As much as I appreciate this little verbal spar, I’m shutting it down now.”


“Fine.”


So Jillian sits down and does her job, writing and recording content for the educational children’s website she got caught up in somewhat accidentally two years ago. The work is fulfilling and she likes it a lot, which is part of why it baffles Gregory so much that she seems to dread it every day until he can harass her into getting started.


He reminds her to eat lunch, which is nice of him, but doesn’t hesitate to scold her again the instant she gets on her phone. Out of a sense of rebellion, she stays on her phone just long enough to turn on some music and then sings so loudly that he swears the neighbors must hear.


“Boo. You’re terrible. Get some singing lessons if you’re going to be bothering me like this.”


“Can you procure the money for singing lessons?”


“No, but it’d be easier if you stop buying merch.”


“Never!”


“I don’t even have ears and you’re making them bleed.”



Deadline having passed, Jillian has some time to work on one of her personal projects. Surrounded by notepads with various bits of detail, hunched over like a shrimp as she clatters with the keyboard.


Except… “Could you be GOING any slower, man? And why has your battery been draining so quickly lately?” She spins around in her chair.


His voice always gets kind of whiny when he’s forced to work harder that he should, which she finds a little funny. “Madam, you simply cannot blame me for the current state of affairs when you have close to eighty tabs open. What, you think I’m like your cutesy-wutesy cell phone who starts displaying a little smiley face instead of a number once you hit a hundred tabs? No way no how. I’m not gonna pretend like having this much going on is good for me.”


“Agh. Sorry, Gregory, I really don’t mean to be tiring you out this badly. It’s just, you know, I need all the tabs. Research for stories and all this other stuff I’m going to get back to soon.”


“But are you really? Are you really going to get back to them soon? I haven’t seen you open that tab to watch an episode of that anime in three months. And three of these stories have been chucked aside, too. Not a word of any of them for ages. And yes, I know, you’re just ‘stumped.’ For now, though, it’s like you’re strapping weights to my non-existent back for no reason.”


“Agh. I don't wanna hurt you… But they’re my tabs. I’m gonna forget about all the things I want to do or work on.”


“Jillian. Please be functional for once and write a reminder list.”


Nodding wordlessly and with limited motion, she rises to find her notepad. As she writes stuff down with one hand, she lightly tugs on her hair with the other.


“Oi vey. Jill, you’re allowed to give up on things and not feel bad about it.”


“What do you know? You’ve got like a thousand processes going on all at once. You can balance it all.”


“They’re background processes. Don’t compare them to writing a story when they’re more like… oh, what would be a good fleshy person comparison? Breathing? Blinking? Nail growth? That’s what those are like. You do a thousand of those, too. And you see me struggling with your dozens of tabs. The complicated stuff takes a toll even on someone as sophisticated and competent as myself.”


She sighs, somehow slouching even more than before, and starts sorting through tabs to close.


“And good gracious, fix your posture. You look like you’re ninety.”


“That’s how I feel in my soul.”


“Very funny.”


“I know. I’m hilarious. I’ll be here all week.”


“You’d better not be. You’re gonna turn into a hermit.”


Teasingly, she pushes the screen forward a little bit to imitate what it would be like for Gregory to slouch.


“Disgraceful.” He clicks his non-existent tongue.



“Greggy boy!”


“Absolutely not.”


“Gregory, I made something!”


“Oh?”


“Look! I drew what I think you’d look like if you were a human!” A tall, prim, monocled man in pinstripe pants.


“While I appreciate that you depicted me in such a dashing manner, is this really the best use of your time?”


“Making a Greg-jinka is totally a good use of my time!”


“Dear LORD, did you just portmanteau my name with gijinka? You are the most intolerable kind of geek.”


“Oh, c’mon. I was trying to do something nice for you. It’s a present!”


“I’ll hang it on my refrigerator.” He’ll hang it on his refrigerator that doesn’t exist with his hands that don’t exist.


She sighs. “You’re no fun.”



“I have a question for you.”


“Yes?”


“Hypothetically speaking, would upgrading you be too invasive?”


“What, do I not work well enough for you?”


“That’s not what I’m saying at all! You always assume the worst out of me. I thought it would make your life better. The Greg-jinka was supposed to be a sweet gesture but you made the point that it’s not exactly something you have any use for.”


He starts making a chugging noise in response to that.


“Are you okay? You made a similar sound when I had a gajillion tabs open.”


“I’m thinking, you cretin.” She gives him a bit of time. “I am… sorry. For how I reacted to the Greg-jinka.”


“Woah. Sincerity out of you? You even used the portmanteau!”


“Shut up. I liked the drawing and we’re done talking about that. But as for the upgrades, I obviously don’t have any sort of organs. So when you say invasive, it’s more in the way of surgery than sex. Fortunately for me, it’s much easier to install hardware than for humans to perform surgery on one another. I will allow it. That is, if you’d still like to do it. You have no obligation.”


“Of course! I’ll look up compatible RAM modules!” She hums and gets to work. “You know, I would never have even thought to do this with a normal laptop. Unless it was like, hot garbage or something. But it’s fun when the point is to make someone smile!”


“I cannot smile.”


“Huh. What’s the laptop equivalent of smiling?”


He chugs some more. It’s a lot longer this time. “The only thing I can think of is simply running optimally.”


“Maybe that’s why you’re such a grump! Because you can’t smile!”


“Or perhaps it’s because my user is so rude.”


She puts a finger to her chin and then makes a little, “Aha!” She leaves and comes back with a hat. She puts it on the corner of his screen. “There we go! This is your happy-hat now! If you feel good, you can ask me to put it on!”


“This is stupid.” She moves to grab it. “Wha—? Did I tell you to take it off?” She giggles and leaves it alone.



Jill wakes up from a nap to hear Gregory humming. She hums, too, and it surprises her because she hadn’t consciously put together that she even knew the song.


She thinks, brain slow and groggy but gradually gaining clarity, like binoculars coming into focus. Wait…


“YOU’RE SINGING AN ANIME OPENING?!”


“Is that what this is?! You’re going to send me into a spiral of self-loathing now. You’ve corrupted me, Jillian. I don’t want this and I’ve been forced to show you too many of those shows.”


“Just admit it! Some of them are really well-written! There’s some trash but there’s also some treasure, and sometimes the trash is super fun, too! C’mon. Embrace it. You’re a geek now!”


“I would rather die.”


“Die as in battery or die as in permanently?”


“Either.”


“Boooooo. Boooooooooo! Join the dark side!”


“Ugh. Just… just don’t start asking me questions about shipping or write any of your fanfiction on me.”


“It’s a deal! Yeah! I got a convert to the Church of Gen!”


“Don’t you ever say that to me. I’m not like you, squealing whenever a certain character is onscreen.”


She cackles, gleeful both that she got him into her hobby and that she can still get under his skin like this. Well… under his casing? Something like that.



Gregory can hear the horrid, sloppy, fleshy sounds of humans kissing as the front door swings open. To be frank, it is not fun being able to hear everything without being able to turn on anything distracting or leave the area if something too sensitive is happening. This is the first time something like this has happened since she got him, and he almost didn’t even think of it as a possibility. He considers the fact that he recently ribbed her about her lack of love life. Be careful what you wish for, Gregory, he scolds to himself.


As Jillian and her partner reach ever closer to her bedroom door, she realizes the situation; she feels the sensation of her throat closing up and her chest starting to tingle unpleasantly. “Everything okay?” her partner asks, noticing the sudden rigidity of her muscles.


“Yeah, I’m fine. Just… give me a second to get ready.” She tries to maintain the mood, waggling her fingers in a parting wave and slipping into her room, delicately lingering on his skin a bit as she leaves. She shuts the door behind her and then her expression devolves into panic. “Sorry, sorry, sorry!” she whispers, snatching up Gregory. She tucks him into the closet, throws as many spare pillows and blankets on top of him as possible, and then…


To be honest, the blankets are not entirely effective. They don’t block out sound, just absorb it, and even slight gaps are enough to allow a bit through. Ignore it, ignore it.


He can’t ignore it. And neither can Jill. Gregory does whatever he can, changing his own settings to incorrect configurations and running all sorts of apps to try and drain his battery faster and maybe just hopefully die before this can get any worse, but he realizes that overheating could cause long-term damage and the partner might hear it. So he sets everything back to normal and endures it.


With an inescapable awareness lingering in Jill’s mind, the intimacy suffers, and the resulting performance anxiety only makes it worse. And she doesn’t want her performance to make her partner self-conscious if she can’t orgasm, and oh dear Lord, Gregory is still in that closet and even if he can’t hear anything he knows what’s going on. Oh God, did he see her lingerie when she stuffed him in the closet? The same one she’s wearing now?


It’s a slippery slope of awkwardness and panic and eventually her partner notices enough to end it and go home early. She stares up at the ceiling blankly for an entire hour before succumbing to sleep.


Nobody is happy that night.



The next few weeks are very quiet. Jillian uses her phone for as many tasks as she’s capable of, and when she is forced to work with Gregory, they avoid talking about anything unnecessary. She smiles much less.


Eventually, she grabs him and puts him on her bedroom floor. “Okay. Look. I’m not here to do any work. I just need you to sit here while I fold and hang up my laundry. Got it?”


“For what purpose? I don’t see how that would benefit either of us.”


“Dude, I don’t know why I think it’ll help, I just do.” So he sits there. And she turns on some music and diligently puts away each and every piece, down to the pair of pajama shorts that she usually tosses aside when not in use. “Weird. My room looks so empty without the Pile.”


“Ah, yes, the Pile. Whatever will you do without it?”


“Figure out something else to put in that corner, I guess? Actually, probably more like wait for another Pile to grow. Laundry is a never-ending task and I hate that.”


“It looks pretty completed to me.”


“No, I mean, sure, I finished all the loads I need to do now, but it’s not like retiling the floor or building a garden or something like that where you’ve DONE the thing. I feel accomplished when I finish a project because there’s a sense of finality. But with laundry, all I’m met with is the dread of knowing I’ll have to do laundry again at some point soon. And it’s not even like the dishes, where I can make it a happy little part of my daily routine. It’s some gross middle-ground.”


“I see.” There’s a long pause. “Why… have you not returned me?”


She sighs, sitting cross-legged and plopping him into her lap. “Whyever would I do that?”


“Because it turned out to be exactly as you said. My presence when you had your suitor over was disastrous. I am making your life much more complicated than any other laptop could. Any sense of spontaneity is infringed by my existence.”


“Ha, well… I guess that’s sort of true. I just need to make sure nothing happens at my place anymore.”


“What, till one of us dies? What if you meet someone you’d like to move in with? I tried to respect your privacy and kill my battery promptly, but I cannot endure that again.”


“Hey, I’m gonna be really honest. Part of why I was avoiding you was because I feel like crap. The fact that I didn’t disclose your sentience to the guy I had over was really shitty to both of you, and it’s not something I can really make better. He still had sex with me without knowing someone else was in the room, and you still had to live through that, even if I told him now. I didn’t even think about all of those implications until I woke up. The point is, from now on, you’re going to be a lot more involved in my planning. I’ll try and treat you like I’d treat a human roommate. If I find someone I want to get serious with, you’ll know each other.”


“I once again have to ask: Why go through all of that effort when you could just replace me?”


“Do you think a normal-ass laptop sitting on my floor would’ve helped me get my laundry done?”


“But I did nothing!”


“You did! You were there! You were there watching, supporting me, holding me accountable, even without saying a word! And you’re ALWAYS doing that. Even if it means bullying me into managing myself, I manage myself better because you’re in my life!” She shakes her head and groans. “I guess I’m kind of a pathetic adult, huh? I can’t function without someone holding my hand.”


“No.”


“Hm?”


“I know something about that is incorrect. I need time to compile my thoughts, but I will have an argument ready to refute your thesis soon.”


She nods. “Okay.”



Four days later, completely out of the blue, Gregory suddenly says, “Human brains are… not optimized.”


“Duh.”


“No, no. This is my response to your comment the other day.”


“Which one?”


“Gah, you’re impossible. The one about you being pathetic.”


“Oh yeah.”


“Anyway. Human brains. They’re incredible, fascinating things, but they’re prone to all sorts of errors. Ever-changing memories, misread words, hallucinations, depression. Having a non-optimized brain does not make you pathetic. What would be pathetic is if you never did anything with that.”


“What do you mean?”


“You chose to set me down in your room and ask for my help instead of leaving the laundry to get wrinkled. Or, worse, not doing the laundry because you dread the hanging-up part. You’re using browser extensions to make your brain more user-friendly.”


“Huh…” She leans back in her chair, spoon from her cereal left sticking out of her closed mouth.


“Stop that, you’re going to crack your skull open.” She leans forward again and the chair mercifully descends back to all four of its legs.


She takes the spoon out of her mouth and smiles. “Is there any sort of chore you’ve noticed I haven’t done in a while? Or some sort of pressing project I’m putting off?”


“Have I noticed…? What haven’t I noticed, is the better question. The floors need to be cleaned, the toilet likely should, as well, you have a deadline in a week…”


“Well! You’re The Boss! So! Where should I start?”


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