Quirky Questions to Engage a Guy – Try These!

When it comes to getting to know someone, asking the usual conversation starters can feel a bit mundane. If you’re looking to add some excitement and intrigue to your conversations, why not try asking some weird questions to ask a guy? These offbeat and unexpected questions can spark curiosity and create memorable moments. Whether you’re on a first date or trying to deepen a connection, these unique questions are sure to make the conversation stand out.

In this article, we’ve gathered a variety of quirky and thought-provoking questions that you can use to engage a guy. From fast food horror stories to discussions about the future of dating, these questions will take your conversations to a whole new level. So, next time you’re looking to break the ice or steer the conversation in an interesting direction, give these weird questions a try. Get ready for some unexpected answers and memorable conversations!

What’s your fast food horror story?

Fast food has become an integral part of our modern lifestyle. Whether it’s a quick meal on the go or a guilty pleasure, it’s hard to resist the convenience and taste of fast food. However, sometimes things can go terribly wrong, leading to fast food horror stories that make for unforgettable experiences.

Have you ever had an encounter with fast food that went completely off the rails? Maybe you found something unexpected in your burger or experienced a stomach-churning incident that left you scarred for life. Share your fast food horror story and let’s dive into the weird and bizarre side of fast food.

Urban myths and strange tales about fast food are abundant, from the infamous finger in the chili to mysterious ingredients. This question opens the door to intriguing discussions about the strange and memorable encounters people have had with fast food.

So, what’s your fast food horror story? Share your experience and let’s uncover the dark, and sometimes hilarious, side of fast food together.

Fast Food Horror Story Restaurant Experience
1 McDonald’s Found a cockroach in my fries
2 Burger King Ordered a cheeseburger, got a bun with no patty
3 Taco Bell Discovered mold on my taco
4 KFC Chicken not fully cooked
5 Subway Accidentally served meat to a vegetarian customer

What game do you dominate when you play it?

Games have a way of bringing out our competitive spirit and showcasing our skills. Whether it’s a physical sport, a virtual video game, or a strategic board game, everyone has a game they excel at.

When trying to engage a guy in conversation, asking about the game he dominates can be a great way to spark his passion and competitive side. It’s an opportunity for him to showcase his abilities and share his love for the game.

So go ahead and ask that guy what game he dominates. Is he a basketball champion on the court, a master tactician in a game of chess, or a Jedi knight in the virtual world? You might be surprised by his answer.

What scene from a movie scarred you for life?

Movies have the power to leave an indelible mark on us, sometimes through scenes that haunt our memories long after the credits roll. Asking a guy about a movie scene that scarred him for life can open up intriguing conversations about his taste in movies, his emotional responses to certain scenes, and the impact of storytelling on our lives.

Whether it’s a horrifying moment from a horror film, a heartbreaking scene from a drama, or a disturbing sequence from a thriller, this question delves into the depths of our fears, emotions, and cinematic experiences. It allows us to explore the movies that have made a lasting impression and shaped our perspectives.

For example, he might recall the chilling shower scene from Alfred Hitchcock’s “Psycho” or the relentless horror of the Upside Down in “Stranger Things.” By sharing his scarred movie scene, he not only reveals his preferences in genres but also provides insights into his emotional depth and the kind of stories that resonate with him.

Through this conversation, you might discover shared movie interests or find recommendations for new films to explore together. Remember, the power of movies lies in their ability to transport us to new worlds, evoke strong emotions, and spark conversations that go beyond the screen.

movie scene scarred for life

Movie Scarred Scene
Psycho The shower scene where Marion Crane is brutally murdered.
The Shining The elevator blood scene.
Requiem for a Dream The disturbing hallucination scenes.
The Exorcist The possessed girl crawling down the stairs upside down.

What is your hometown best known for?

Everyone’s hometown has something unique or interesting about it. When getting to know a guy, asking about his hometown can be a great way to learn more about his background and spark nostalgia-filled conversations about the past. So, what is your hometown best known for?

What’s the most important file on your computer?

When delving into a guy’s digital life, an intriguing question to ask is about the most important file on his computer. This query not only satisfies curiosity but also reveals surprising insights into his interests and priorities.

Each person has their own unique collection of files, from photos and videos to documents and music. By discovering the most important file, you gain a window into what holds significance for him.

Perhaps the guy has a meticulously organized folder of cherished memories, like a collection of family photos or videos of milestone moments. Or maybe his most crucial file is his meticulously crafted resume, representing his valued career aspirations and achievements. It could even be a treasured collection of digital artwork, showcasing his creative passion.

In sharing the story behind his most important file, the guy unveils a piece of his personal story, offering a glimpse into his past, present, or future. It could be a cherished memory, an ambition, or a testament to his passions.

Asking about the most important file on a guy’s computer not only provides an opportunity for dialogue but also fosters a deeper understanding of his values and interests. It’s an intriguing and unexpected question that can lead to engaging discussions and further exploration of each other’s digital lives.

What’s the Future of Dating?

When it comes to the future of dating, the possibilities are both exciting and unknown. With technology advancing at an unprecedented rate, it’s no surprise that the world of dating is also evolving. One peculiar way to explore this topic is by asking guys their thoughts on the matter. By posing the question, you open up a realm of imagination and gain insight into their views on relationships and technology.

Asking a guy about the future of dating might seem like an unusual question at first, but it can lead to fascinating discussions. Depending on his interest in sci-fi and futuristic concepts, you might get a unique and imaginative answer that sheds light on his vision of relationships.

Some guys might envision a future where dating is heavily reliant on advanced AI algorithms, virtual reality, or even holographic companions. Others might anticipate a return to more traditional forms of courtship, focusing on genuine connections and face-to-face interactions. The responses will vary, offering a glimpse into their mindset and aspirations when it comes to romantic relationships.

The future of dating is likely to be a blend of technological advancements and fundamental human desires. While innovative apps and platforms may continue to shape the way people meet and connect, the importance of human connection and emotional bonds will remain constant.

As the line between the digital and physical worlds continues to blur, it’s crucial to keep these questions in mind and reflect on the potential implications of future dating trends. And who knows, maybe you’ll discover a shared vision of what lies ahead!

future of dating

Key Points

Benefits of Exploring the Future of Dating Implications of Technological Advancements The Importance of Emotional Connection
– Sparks insightful discussions – AI algorithms and virtual reality – Fundamental aspect of human relationships
– Unleashes imagination and creativity – Holographic companions – Blending digital and physical worlds
– Identifies shared visions – Balancing technology and tradition – Future trends and potential challenges

Exploring the future of dating with alternative and unexpected questions not only ignites engaging conversations but also provides valuable insights into the minds of the guys you’re talking to. By embracing the unknown, you open the door to endless possibilities and gain a deeper understanding of the ever-evolving world of relationships and technology.

What, besides wealth, do you never have enough of?

This question allows the guy to reflect on his desires and priorities beyond material wealth. Find out what he values and craves in life, whether it’s love, adventure, knowledge, or something else. The answers can be varied and provide insight into his passions and aspirations.

When it comes to measuring wealth, the treasures that hold the greatest value cannot always be found in a bank account. While financial stability is important, true richness lies in the intangible aspects of life. By exploring the depths of a guy’s desires and aspirations, this question opens the door to a deeper understanding of his inner world, shedding light on what truly brings him joy and fulfillment.

When you ask a guy what he values and craves beyond material wealth, you create an opportunity to connect on a more meaningful level. It allows him to express his interests, dreams, and ambitions, offering a glimpse into his soul.

For some, the answer might be love. They seek meaningful connections, cherishing the bonds they share with others. Love provides the warmth and support that money can’t buy, making it a priceless treasure in their eyes.

Others might crave adventure. They yearn for excitement and exploration, seeking to push boundaries and break free from the confines of routine. Whether it’s traveling to new places, trying daring activities, or embracing the unknown, these individuals find fulfillment in the thrill of the unknown.

Knowledge is another valuable asset. Some individuals have an insatiable thirst for learning, constantly seeking to expand their understanding of the world. From books to documentaries, they relish in the acquisition of wisdom, viewing knowledge as a pathway to personal growth and enlightenment.

Of course, these are just a few examples. The possibilities are endless, and the answers can vary greatly from person to person. What matters most is the insight gained from these conversations. By asking this thought-provoking question, you can uncover the passions and aspirations that drive a guy’s life, gaining a deeper appreciation for the complexity and richness of his character.

So, the next time you’re looking to engage a guy in conversation, go beyond the surface and ask what he never has enough of besides wealth. You never know what hidden treasures you may discover.

What’s something you’ve done that you would try to dissuade anyone from doing?

Share embarrassing experiences! Ask the guy about something incredibly stupid he’s done and encourage him to tell the story. It’s only fair to reciprocate by sharing your own embarrassing moments too. This question can create a lighthearted and fun atmosphere while getting to know each other better.


These weird questions to ask a guy can help spark interesting and memorable conversations. By exploring topics such as fast food horror stories and the future of dating, these thought-provoking questions offer a unique twist that sets them apart from the usual conversation starters.

Don’t be afraid to step outside of the norm and ask unconventional questions that engage the guy and make the conversation stand out. Delve into his experiences, preferences, and memories, allowing for deeper connections and a better understanding of each other.

Remember, these questions are designed to create moments of curiosity, surprise, and nostalgia. So the next time you’re looking to have an engaging conversation with a guy, try these weird and thought-provoking questions to make it a truly memorable experience.