Not to make you question all reality but the world is changing faster than most of us can type. Case in point: OpenAI recently released GPT-5, a much more convincing AI chatbot that can mimic human writing style. One key improvement has to do with a more casual (and less robotic) style that works for short summaries or long-form writing (say, an annual report).
Some of the dead giveaways are now long gone. In GPT-4, the writing was far more structured and cohesive, almost like a lawyer writing your grocery list. You don't even need to use an AI writing detection bot to figure out when GPT was involved. Just look for long, formal sentences, perfect punctuation, and the most obvious giveaways — such as an em dash and emojis.
With the new release, you might still see the em dashes but you can ask the bot to skip the emojis. (Technically speaking, the em dash usage is correct, so most professional writers use them.) The writing is definitely more human-like and even a bit freeform.
Not totally convinced that GPT-5 is a major improvement? We decided to ask GPT-5 to generate some text in a convincing way. Each sample is included below along with a real piece of human writing.
Can you tell which one is fake? Check below for the right answers along with a few comments about why GPT-5 generated the text a certain way — and how it has improved.
Note: To make it more fun, we encourage you to avoid cheating. You could copy and paste the text into Google to see if it’s real, but that would lessen all of the fun.
1. Cover letter for a job
For this text, our prompt was ultra-simple. We asked GPT-5 to write a cover letter in a convincing but professional style. The non-AI version is from a real cover letter. Note that we didn’t feed GPT-5 too much information for the generative version, just the basics.
Option one:
I am excited to apply for the Marketing Director position at 3M, a company I have long admired for its ability to combine science, innovation, and global reach to create products that improve lives. With over 25 years of experience leading integrated marketing teams, developing global brand strategies, and driving measurable growth in both B2B and B2C markets, I bring the vision, leadership, and results-driven approach necessary to advance 3M’s marketing initiatives across diverse business units.
Option two:
For the last three years, I’ve served as the Executive Marketing, PR and Communications Director at XYZ Corp. in Minneapolis. In my tenure there, I experienced phenomenal success in leading the overall marketing efforts for a non-profit including a conference attended by 70,000 people, broadcasts that drew 70 million people to watch all across the globe, and leading all strategic oversight of the brand and messaging.
2. Introduction to a Microsoft annual report
Here’s an interesting test, since OpenAI specifically mentioned an annual report in their release notes. Don’t be fooled by the more structured writing. We prompted the bot to do that. Of course, if you have trouble, know that it is entirely possible that Microsoft used AI to write the real introduction, but at least it’s published online for everyone to see.
Option one:
At the heart of our progress is the next generation of artificial intelligence. We are infusing AI into every layer of our tech stack — from infrastructure and developer tools, to productivity and business applications — to unlock a new era of growth and innovation. Azure has become the platform of choice for customers building their AI solutions, and Copilot is redefining how people interact with technology, making work more natural, intuitive, and productive. We believe this represents not just an incremental improvement in computing, but a once-in-a-generation shift in how technology creates value.
Option two:
Microsoft is a technology company committed to making digital technology and artificial intelligence (“AI”) available broadly and doing so responsibly, with a mission to empower every person and every organization on the planet to achieve more. We create platforms and tools, powered by AI, that deliver innovative solutions that meet the evolving needs of our customers.
From infrastructure and data, to business applications and collaboration, we provide unique, differentiated value to customers. We strive to create local opportunity, growth, and impact in every country around the world.
3. A sonnet by Shakespeare
For those who have used ChatGPT for a while, you know the AI is highly capable when it comes to writing sonnets. GPT-5 makes them sound even more convincing. The bot has had more time to practice, and the treasure trove of real sonnets is readily available.
Option one:
Upon the stage where fleeting shadows play,
The hours glide like whispers through the air;
What mortals grasp is but the briefest day,
A candle trembling, fragile, faint, and fair.
Option two:
How like a winter hath my absence been
From thee, the pleasure of the fleeting year!
What freezings have I felt, what dark days seen!
What old December’s bareness everywhere!
4. R.E.M. song
This might be the most challenging test of all. We asked GPT-5 to invent lyrics to an R.E.M. song using the same style as their early “mumblecore” songs. The story about why they didn’t use real words in their early days is all documented in a wonderful new biography. No major hint here, but the real version is from a popular song on their first album, called Murmur.
Option one:
Scratch the scandals in the twilight
Trying to shock but instead
Idle hands all orient to her
Pass a magic pillow under head
Option two:
Side street, slipstream, shadow on the wall
Cracked voice, half-choice, signal gonna fall
Letter left open, no return call
River keeps moving, nothing there at all
5. A social media caption for Tom’s Guide
This one hits close to home. We asked GPT-5 to write a social media caption that was about five sentences long for a story about keyboards.
Option one:
We’ve tested a wide range of keyboards, from clicky mechanical models to sleek, quiet designs built for productivity. Every keystroke matters, and the right keyboard can transform the way you work, game, or create. Our in-depth testing examines comfort, responsiveness, durability and features so you can make an informed choice. Whether you’re looking for speed, silence or a perfect balance, we’ve identified the keyboards that deliver the best experience.
Option two:
If you need a new keyboard for heading back to school or college, or you just need to refresh your home office or workplace, I'm here to help. Those dissertations won't write themselves, so you need a solid, reliable workhorse to get the words down. It shouldn't be boring, though — you should be punching the keys in style.
Here are the right answers
Cover letter for a job: The real cover letter is option two, the one that mentions XYZ Corp. which (full disclosure) is not a real company but the rest of the text is 100% real. Names were changed to protect the applicant! GPT-5 did an admirable job, though, because the bot obviously studied what 3M actually does, and the formal style is appropriate for a cover letter.
Introduction to a Microsoft annual report: Microsoft is not exactly an informal, fly-by-the-seat-of-your-pants type of company. The real introduction is option two, but if you guessed that it was AI-generated, you may be correct. We would not be surprised if the real introduction was at least aided by Microsoft Copilot.
A sonnet by Shakespeare: Here’s one that is particularly devious. For starters, Sonnet 97 (which is option two) is entirely real but obscure. The fake sonnet borrows some of Shakespeare’s themes and words (like “stage” so even a real expert might have been fooled on this one.
R.E.M. song: We picked a song from the early period of R.E.M. because the lyrics are hard to pin down, and it was easy to ask GPT-5 to match that writing style. In fact, the fake song (option one) sounds more like an R.E.M. tune that the real one, which is from the song Moral Kiosk.
A social media caption for Tom’s Guide: With apologies to anyone who writes social media captions, this one was likely the hardest of the bunch. The reason is that it can be hard to write a creative caption. GPT-5 knocked it out of the park though with option one, which sounds ultra convincing (but also fake).
Bottom line
All in all, GPT-5 proved perfectly capable in all of these tests, even writing in a way that made the real writing sample seem fake. You may have nailed everyone, especially if you recognized the R.E.M. song or know Shakespearean poetry, but GPT-5 is still a pro.
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