Can You Really 'Outsmart' ChatGPT?


Who would have thought ChatGPT, Claude, and other large language models would become an essential part of what we do - whether at work or play. Back in the day, I often get called a 'walking encyclopedia' because friends and family alike tend to think that I'm a 'know-it-all.' The truth is that I read a lot of books and magazines growing up as my mom used to borrow my uncle's complete collection of Encyclopedia Britannica or the often neglected copies of National Geographic magazines from her office.

These days, people tend to ask these artificial intelligence (AI) platforms a lot of things from getting their research work completed in no time, asking for solutions to everyday problems, and even writing an email to get a job. The point is that AI is everywhere. We have become so dependent on these technologies that even our capacity to think and create is now outsourced to a machine.

We, humans, have built sophisticated AI models to augment repetitive and time-consuming tasks. Many of these AI models have become better and better and we keep on developing and iterating new ones. In fact, machine learning has helped it learn things on its own as more data is added. That means, the more we interact with them, the more they will learn about us and the world. Let's not forget that there are still areas where they could stumble and fall. One of these things is - logical paradox.

Does it mean, we can ask them things where they are more likely to hallucinate outrageous things? In short, can we really outsmart them?

What's It Good At?

I try to 'engineer' prompts the best I can since I don't have premium subscriptions to the latest AI platforms right now, including ChatGPT and even Claude to a certain extent. I try using prompt templates so I can make use of this platform even on the free version.

I have to say, that there are three key areas where ChatGPT is good:

  • Language Mastery: It's called a large language model after all so it's trained in a large data set - even larger than the entire lost collection of the Library of Alexandria and all the ancient literature combined. It doesn't just understand words, it also comprehends what you ask for as if you're talking to someone who is a subject matter expert of just anything there is. It can spit out a response in mere seconds without having to stop and think about it (well, kind of at times though).
  • Swiss Army Knife: But wait, there's more! It's a master of many. Need a poem? a story? a piece of code? Look no further. ChatGPT can surely deliver. Its capabilities excel at tasks that would leave most people scratching their heads in awe. Think about it as a do-it-all chatbot that will answer your questions no matter what.
  • Ever-Growing Library: What makes ChatGPT special? It's a living library, stacked to the virtual rafters with information spanning the vast expanse of human understanding. From ancient history to cutting-edge science, from classic literature to Internet memes, there's hardly a topic it hasn't explored. With its vast knowledge base, it tackles every challenge effortlessly.

Where It Falls Short?

As much as we all marvel at the language and problem-solving capabilities of ChatGPT, it falls short in several key areas. Its limitations serve as critical reminders that there are situations where we can game the system and trick this AI platform.

1. Lack of True Comprehension and Reasoning
At its core, ChatGPT operates through pattern matching rather than genuine comprehension and reasoning. It excels at recognizing and reproducing patterns based on its vast training data, but it lacks the nuanced understanding that humans possess. For example, while it can generate coherent responses to questions about historical events or scientific concepts, it may struggle to grasp the underlying significance or context. It can mimic human-like responses but can't comprehend the concepts it discusses.

2. Biases and Inconsistencies
Another challenge is the presence of biases and inconsistencies in its responses. These biases stem from the data on which it was trained, reflecting societal biases and prejudices. Moreover, its responses may vary depending on the phrasing or context of the input, leading to inconsistencies in its output. This underscores the importance of critically evaluating the information provided by AI systems.

3. Handling Contradictions
ChatGPT struggles to resolve contradictions seamlessly and oftentimes, responds with its own answers. It may generate responses that sound logical, but it sometimes lacks a deep understanding of concepts thereby leading to incorrect or inconsistent answers. Apart from that, it has problems providing reasoning about the validity of its responses, correcting assumptions, or providing factually correct answers iteratively thereby leading to self-contradictions at times.

4. Limitations in Adaptability
Despite its ability to summarize known information and generate scripts, ChatGPT struggles to adapt to specific queries or engage with topics. Some experts believe that its capabilities are similar to that of an average high school student, who regurgitates facts but lacks deep engagement or mastery of the subjects. Its limitations in understanding and adaptability may restrict its utility in more complex or nuanced contexts.

5. Fixed Intelligence
Once it outputs an answer, the intelligence is fixed and additional rationalizations afterward don't change the quality of the answer. It may be able to generate solutions but it may need clarification or guidance to produce accurate or sensible output. It performs better when given prompts that encourage them to think through a problem step by step.

Outsmarting Artificial Intelligence

Most people think that outsmarting artificial intelligence might be futile. While some think that it can be done. In fact, we humans are naturally inclined to test its limits by exploring the vulnerabilities and exploits where we can stump the most sophisticated AI models with cunning strategies, logical puzzles, and confusing paradoxes.


Let's explore various tactics that we can employ in our quest to outsmart ChatGPT.

Some Strategies

When faced with a sophisticated AI, we might resort to various strategies to test its capabilities and probe for weaknesses. Some common tactics include:

1. 'Jedi Mind Trick' Questions
We can devise cleverly crafted questions or scenarios designed to confuse or mislead ChatGPT by testing its ability to discern intent and provide accurate responses.


2. Probing Weaknesses
By deliberately exploiting known limitations or biases in its training data, we can attempt to reveal vulnerabilities in its understanding or reasoning abilities.


3. Logical Paradoxes
We can use paradoxical statements or scenarios in an attempt to elicit contradictory or nonsensical responses. Some classic examples include:
  • The Liar Paradox: Presenting the AI with statements like "This statement is false" can lead to a paradoxical dilemma, as affirming the statement leads to a contradiction, yet denying it also results in a contradiction.
  • The Barber Paradox: Asking the AI to resolve the paradox of a barber who shaves all those who do not shave themselves can expose the limitations of its reasoning capabilities.

4. Assessing Vulnerabilities
ChatGPT's response to paradoxical scenarios offers insights into its understanding of logic and self-reference. While it may generate responses that appear coherent on the surface, deeper examination often reveals inconsistencies or contradictions.
  • Limited Contextual Understanding: It may struggle to grasp the underlying context or implications of paradoxical statements, leading to superficial or nonsensical responses.
  • Pattern Matching vs. Reasoning: In paradoxical scenarios, it may rely on pattern matching rather than genuine reasoning, resulting in responses that fail to resolve the inherent contradictions.

5. 'Infinite Loops'
This scenario poses a significant challenge for conversational AI systems. When confronted with certain queries or commands, these systems may enter into loops that continuously generate responses without reaching a satisfactory conclusion.
  • Resource Consumption: Infinite loops can consume computational resources and degrade the performance of AI systems, potentially leading to system instability or unresponsiveness.
  • User Frustration: From a user perspective, encountering an AI caught in an infinite loop can be frustrating and counterproductive, undermining the system's reliability.

As we continue to explore the boundaries of ChatGPT's intelligence, understanding its vulnerabilities in dealing with these issues is essential for refining its capabilities and enhancing its stability in real-world applications.

The Big Question - Why?

We all want to have a conversational chatbot that can answer all questions whatever it may be. Yet, there is that desire to outsmart the smartest thing there is - whether it's intellectual curiosity to practical concerns about AI's impact on society.

There is that challenge to test our wit and creativity against a cutting-edge system. Remember the time when chess grandmaster Gary Kasparov defeated Deep Blue? Well, AI went on to win against human chess players as iterations made improved versions of it. We have long been fascinated by the prospect of creating intelligent machines and that's why we are keen to explore the boundaries of our own ingenuity.


For developers, outsmarting AI is one way to pressure test these systems to ensure safety and reliability. That way, potential risks and vulnerabilities are uncovered that could compromise performance or lead to unintended consequences.

As AI technologies become more pervasive, there is a growing concern about their impact on human autonomy and decision-making. Outsmarting AI is our own way to override future designs AI may have on us. It's one way of preserving human autonomy. AI systems should be developed to complement, not replace, human intelligence.

The Future

As we explore the complicated digital landscape, it's important to acknowledge a future where humans and AI can collaborate effectively while understanding the unique strengths and limitations of each.

One prevailing vision for the future of AI is one of collaboration rather than competition. In this model, humans and AI systems work together, each leveraging their respective strengths to achieve common goals. ChatGPT and similar AI platforms excel at processing vast amounts of information quickly and generating responses in natural language. This capability can complement human decision-making processes by providing timely insights and suggestions. For example, in fields like medicine and law, AI assistants can help professionals sift through large volumes of data to identify patterns and trends, allowing humans to focus on more nuanced tasks that require empathy, creativity, and critical thinking.

While AI systems like ChatGPT possess remarkable abilities, they still lack certain qualities that are inherently human. Skills such as emotional intelligence, empathy, and moral reasoning are difficult for AI to replicate convincingly. As such, there is a growing emphasis on the need for humans to cultivate these uniquely human attributes. By developing skills that AI cannot easily replicate, such as creativity, adaptability, and ethical judgment, humans can carve out distinct roles in an AI-driven world. Furthermore, fostering interdisciplinary collaboration between AI researchers, ethicists, psychologists, and other experts can help ensure that AI systems are developed and deployed in ways that align with human values and priorities.

The widespread adoption of advanced AI assistants like ChatGPT raises profound ethical questions about their impact on society and individuals. One notable concern is the phenomenon of "enshittification," wherein AI systems perpetuate or amplify harmful biases and misinformation present in their training data. This problem underscores the importance of ensuring that AI systems are trained on diverse and representative datasets and that their outputs are regularly monitored and evaluated for fairness and accuracy. Additionally, there are broader ethical considerations related to privacy, consent, and accountability that must be addressed as AI technologies become more integrated into everyday life.

In conclusion, the future of human-AI interaction holds tremendous promise, but also significant challenges. By embracing a vision of collaboration, cultivating uniquely human skills, and addressing ethical considerations head-on, we can harness the power of AI to augment human capabilities and create a more inclusive and equitable society. However, this vision can only be realized through thoughtful and deliberate action, guided by a commitment to the values and principles that define us as humans.

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