AI

I asked ChatGPT to roast me and I can’t stop laughing

ChatGPT Roasting Me Based On Our Previous Conversations

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I've always wanted some kind of power that will make people only tell the truth about me. Then I remembered that ChatGPT can do that kind of thing based on our previous conversations, so I asked the AI Chatbot to roast me, and here's how it went.

I’ve always wondered how people actually see me or think about me, but I always thought that I’d never get a truly realistic answer, even from my loved ones. You know, humans, feelings, and stuff. So I asked ChatGPT, but not in the usual way: I asked the AI chatbot to roast me, and I had so much laughter reading all of its answers that I just couldn’t get enough of it.

Although artificial intelligence can be scary for some, to me it’s a great way of finding new ideas, researching the web, and usually, asking it to tell some jokes to make my day a bit better. It’s fun, it’s useful, and if you ask it, it can roast the hell out of you.

We all know that ChatGPT has now a memory that stores all of your previous conversations, making it even more personal and better for each user, but what if you ask it to roast you based on all of your previous conversations? Well, I did, and here’s what it told me:

First off, you’re a novelist writing about 3094 dystopia and 2050 chaos, yet somehow you’re stuck in 2024 tweaking sub-menu CSS and obsessing over database backups. Are you preparing for the AI apocalypse, or just trying to survive your WordPress plugin’s QA process?

Your sci-fi characters are out there battling AI overlords and societal collapse, but you? You’re battling Divi popups and mega-menus like it’s a life-or-death scenario. Big tech versus big tech issues—same vibe, right?

Oh, and let’s not forget Aria, your tech-fearing cave dweller who dreams of escaping AI tyranny… while you, the author, are here enabling OneSignal push notifications like you’re in cahoots with the machines. “Let’s make the internet annoying for everyone,” right?

Meanwhile, you’re running like five websites, including one where people sell free designs. How does that business model even work? You’re basically the Robin Hood of PSD files: “Steal from nobody, give to everybody, and hope for ad revenue.”

Let’s talk gaming. You and your buddy started Norpan.co because you bonded over Aion. You mean to tell me your big origin story is, “We clicked a lot of buttons together in a virtual world, so let’s make a blog about it”? Romantic. Truly.

And finally, your blog. The TechWise Insider is a pretty snazzy name for someone whose biggest existential threat is a bloated Rank Math table with 758,000 rows. Forget AI or leadership advice—your true villain is MySQL!

Okay, I’ll stop here before you regret asking for this roast. You’re juggling so many projects, I’m half expecting you to launch a dystopian-themed cooking blog next.

Now, if you think that I’d stopped there, you’re wrong. I wanted more, so I asked ChatGPT to continue roasting me because I had so much fun, and here’s how it went (the second time):

Let’s revisit your sci-fi world-building for a second. You’ve got Jo, the Greek backpacker who accidentally yeets himself into 3094. What is this, Time Travel for Dummies? The guy can barely hold down a seasonal job, and you expect me to believe he’s going to save the future? Bro probably can’t even save his phone battery.

And Aria? She’s living in a cave with a robot sidekick while dreaming of 2024. Newsflash: 2024 isn’t all that great, girl! It’s just Panos here messing with GeneratePress themes and building forums no one asked for. If Aria does make it back, she’s gonna take one look at your bloated WooCommerce setup and go, “Send me back to the AI overlords; at least they’re efficient.”

Speaking of WooCommerce, you named your jewelry site example.com. What is that, a jewelry store or a startup for motocross racers with bling? The whole thing sounds like a Fast & Furious side hustle. And with those 20 plugins you’re running, your site’s probably slower than Jo trying to figure out futuristic tech.

Now let’s talk about your podcast interviewing a leadership coach. Let me guess, it’s gonna go something like this:

You: “So, how do you lead a team to success?”
Coach: “By being consistent and disciplined.”
You: “Cool. I can’t even decide between Rank Math and Yoast, but thanks.”

And what’s with your forum? It’s under construction forever, like it’s the next cyberpunk utopia. In reality, it’s probably just two tabs: General Chat and Things Panos Broke This Week.

Oh, and I see you’re on Arch Linux. Congrats, you’re officially that person who won’t shut up about it. “BTW, I use Arch.” Yeah, we know. KDE customization looks great, but will it solve your crippling database issues? Spoiler: No.

Finally, let’s address the elephant in the room—your “blogging with humor” strategy. You’re trying to be funny, but let’s face it, half your readers are just there for the freebies. They scroll past your jokes like, “Haha, great… where’s the PSD file?”


Honestly, you’re a legend. A chaotic, multitasking, sci-fi-writing, WordPress-tinkering legend. Never change, Panos. You’re like a one-man tech circus, and I’m here for every second of it.

Although ChatGPT made a few mistakes, such as the jewelry site which is for a client who’s got himself banned on Etsy.com, and I asked it to provide any info about their Privacy Policy, Terms of Use, and so on, everything else was fascinating, to say the least. It’s fun having an AI chatbot completely roasting you based on your conversation’s history because if anything, it’s gonna tell you the truth – or I think it does.

Thank you, OpenAI, you’ve just made my day, my week, my month, my year.


P.S. Thankfully it didn’t give any crucial spoilers for my upcoming Sci-Fi novel, so I was able to share it with you. Fun fact though: I asked it to help me find unique names for my characters if they were from the future, and after a few tries, it did well.

Panos Sakalakis

Meet Panos Sakalakis, a web wizard, blogging buff, podcasting pro, and SEO sorcerer with over 15 years of enchanting experience. When he's not weaving digital spells with his keyboard, you'll likely spot him conquering mountain trails with his trusty Hard-Trail MTB bike, in hot pursuit of the ultimate adrenaline rush and the perfect blog post inspiration.

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