What are Funny Questions to Ask a Guy?

For ages, humans have used questions as conversation-starters. We imagine Neanderthals said something like "How's the hunting?" to initiate conversations with the opposite sex.

Even now, questions are still your go-to option when trying to make small talk. However, asking a guy boring questions can make discussions feel like an eternity.

Instead of rattling off generic questions, you can ask ones that elicit laughter from a guy. Funny questions can brighten your conversations with guys and increase their interest in you.

You don't need to be Kevin Hart to deliver funny questions. With a bit of wit and confidence, you can ask hilarious questions that will get anyone laughing.

Need help coming up with goofy questions that add color to conversations? Follow along!

Before delving into funny questions to ask a guy, you must understand why hilarious inquiries are useful in conversations. Infusing humor into your discussions, among many other things, does the following:

1. Increase your uniqueness

   Some men believe females lack a sense of humor. However, you can flip the script and add humor to your private conversations with guys. Jovial women are considered rare, so being humorous can increase your appeal to men.

2. It can strengthen your bond

   Some men hesitate before joking with female acquaintances. They think women are sensitive, and jokes are best left out while conversing with them. You can, however, impress a guy by showing that humor is something you enjoy. This will strengthen your bond once he realizes that you share his sense of humor.

3. Aid dialogue

   Humorous quizzes are perfect for breaking the ice in any conversation. Once you get the guy laughing, chatting becomes a walk in the park.

4. Adds life to discussions

   Physical dates are often engaging since there are little to no distractions to affect discussions. Sending messages online is another kettle of fish altogether.

   Nevertheless, this is very different from online conversations, where numerous other things may divert the individuals' attention. Thus, it's important to make your conversations livelier if you want to hold a guy's attention. One way to increase the "interesting factor" of any conversation is to inject some humor into it. Everyone loves a good laugh, so this will help make your talks more engaging.

As you're aware, funny questions can aid conversations with guys. Here's a list of funny things to ask a guy on your next date:

1. What ignorant beliefs did you have when you were young?

   As kids, many of us believed certain things which turned out to be false. Some, for instance, believed Santa Claus indeed visited homes on Christmas Eve to drop gifts. Your guy is going to find this question funny and give an answer worthy of chuckles. This is one of the best funny questions to ask a guy, which is why it's on top of our list.

2. What is the worst joke you can tell?

   Bad jokes may elicit groans, but they can add some life to a conversation. Ask your guy to hit you with some of the most groan-worthy jokes in his arsenal. If your partner was taciturn before, this is a good way to get him talking. It is why we consider it one of the top funny things to ask a guy.

3. What abilities does he secretly wish for?

   Boys love their superhero movies, and some of them secretly wish they had powers. Even the most serious guy wouldn't resist the chance to answer this question.

4. What stupid decision got him in hot water as a child?

   Because young boys are adventurous, they do a lot of mindless things they end up regretting later. Your guy likely has a story on how he got into trouble for taking an ill-advised decision while trying to have fun.

5. What is your worst hangover experience?

   If a guy drinks alcohol, he'll have a few bad hangover stories to tell. Hangovers are often a funny experience, so his answer will infuse humor into the chat. However, confirm if the guy consumes alcohol to avoid committing a faux pas. Otherwise, this question is one of the best random funny questions to ask.

6. Do you have any weird ideas?

   Some people have crazy ideas that they hide from others to avoid looking like a nutcase. However, men may be willing to discuss their strange ideas in private with someone like you. The answers they give may provide you with insight into their personality and thought process. For example, someone who has crazy ideas on how certain things should work can be quite creative.

7. What is the craziest thing you have done for money?

   At some point, some men have done regrettable things for money. These things don't have to be criminal, and they could be funny (for example, acting as a clown for a few bucks). This question is acceptable in online or offline conversations. Besides, you can use your partner's answer for light-hearted poking in the future.

8. Have you ever been "caught in the act"?

   Getting caught in the act (red-handed) is often an embarrassing event. However, with time, feelings of shame will reduce, and the individual may even joke about it. Your mate's answer to this question can make the talk ten times more engaging. Imagine if he confesses to getting caught stealing cookies as a kid!

9. What is the longest time you wore one pair of boxers?

   Men are legendary for their habitual disregard for personal hygiene. Most males have had a point in their life where they went a long time without switching their underwear. This question will trigger some laughs and increase the jovial nature of the discussion. Thus, we consider it one of the silly questions to ask a guy.

10. What is your secret habit?

    We all have secret habits that few people know about. Oftentimes, secret habits involve a funny activity — which is why we hide them for fear of getting laughed at. Ask a guy, and he'll answer if he trusts you enough. However, you must avoid bringing up his secret habit when in public — that is a violation of trust.

Fun questions are simple and harmless questions that you can ask a guy to know more about him. The right fun questions can leave an impression on a boy and help you build a strong connection with him. Here are some fun questions to ask a guy you like:

1. What things do you have a passion for?

   When you want deeper knowledge of a guy, this is a fitting question to ask. Humans have passions that may influence their decisions. Telling a guy to share his passions is the easiest way to get him talking. In case you happen to share similar passions, that's a big bonus!

2. What is his defining quality?

   Every individual has a trait that defines them. If a guy gives a well-reasoned answer, you will know that he has impressive self-awareness. Additionally, you have to determine if his defining trait attracts or turns you off. Overall, this one ranks as one of the best fun questions to ask a guy you like.

3. What exotic location(s) have you visited?

   This is a good way to judge his desire for adventures and travel. Asking this question is important if you want to find someone who shares your wanderlust and adventurous spirit.

4. What do you consider your biggest achievement(s)?

   This fun question can add some life to an otherwise stale discussion. Men love waxing lyrical about their wins, so this question is bound to evoke a response.

5. Are you a night owl or a morning person?

   Questions like this provide content for discussion with the opposite sex. If your partner picks either of the options, you can ask for his reasons. Knowing his subtle qualities prepares you to handle them when the relationship starts to grow.

Does your guy seem like someone who has a dry sense of humor? Feel free to try asking him weird questions! Whether he's the nerdy or buff type, you'll get answers that are creative, strange, or borderline crazy. Nevertheless, such answers can enliven your face-to-face time and make conversations wonderful. Here are some weird things to ask a guy:

1. Do you believe in any conspiracy theories?

   Everyone knows one or two conspiracy theories since they are popular. In most cases, conspiracy theories are so outlandish that discussing them evokes laughter. Your guy may believe that the Moon has cheese on it, or he may believe that the New World Order secretly controls the world. To make the conversation livelier, add any conspiracy theories that you believe in. That way, both of you can tease each other for believing in such absurd phenomena.

2. How would you want to die?

   This question may seem strange, but hey, you are in the weird questions section! If your guy has no qualms about answering, this question can make the conversation more enjoyable.

3. What technology would you love to witness before your death?

   We all have strange ideas about a futuristic world — flying cars, self-driving vehicles, the list goes on. If your guy loves science fiction, he'll surely give some really cool (and weird) answers.

4. What do you think of UFOs and aliens?

   This is, perhaps, the GOAT of all weird questions. Who doesn't like to talk about extraterrestrials, Area 51, and futuristic technology? Again, you get double points if your guy is into science and loves topics like this. This question will surely trigger an answer even from the most unscientific minds. We recommend it as one of the weird things to ask a guy, whether by texting or in person.

5. Do you want to time travel or be immortal?

   Many of us secretly wish for one of two things: immortality and the ability to travel back in time. Nobody is getting these abilities anytime soon, but they make for pretty interesting conversations.

Not everyone wants to discuss serious issues on a date, especially on the first one. In light of this, selecting a humorous topic to discuss will help launch the conversation smoothly. Here is our ultimate collection of funny topics to talk about with a guy:

1. An embarrassing memory from teenage years

   Teenage years are often filled with several embarrassing events. Talking about them with a guy can be the most hilarious discussion you'll ever have.

2. Uncovering a secret

   Owing to their natural curiosity, boys inadvertently stumble on secrets — at school, home, or elsewhere. This topic can get your ribs cracking if it involves a hilarious event like walking into a parent having an extramarital affair.

3. A lost love episode

   At some point, almost every guy has fallen in love with a girl who wasn't interested in him. Often, this leads to a case of "lost love". While a guy may find discussing his lost love episode embarrassing, he'll see the humor in it and go along with it. You can also share your lost love story to make the conversation more entertaining.

4. An awkward moment

   Without a doubt, your mate has had a few awkward moments in his life, and talking about them can encourage light-hearted conversation. We recommend sharing your super-awkward experiences with him as well. Doing so will signal that you trust him enough to tell him such things.

5. A mischievous action from childhood

   Male children can be incredibly hyperactive and full of mischief. Even if a guy were well-behaved as a child, he'd have a few mischievous actions under his belt. You can ask him to share his most mischievous acts and if he ever got punished for them.

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