28 Random Questions to Ask a Guy

Random questions allow you to initiate interesting conversations and a free flow of communication with a level of comfort around familiar or unfamiliar people. To have a good conversation with a guy, it is good to know some random questions that are appropriate to ask him, and knowing a few key questions to ask may help you strengthen your connections with male colleagues, and make friends out of strangers.

We have provided some important random questions and segmented them according to random conversation starter questions, random questions to ask over text, and random funny questions for a guy.

Random Conversation Starter Questions to Ask a Guy

Here are the important random conversation starter questions for having a good conversation with a guy. These questions give you a good starting point in your conversation with a guy. Here are some random conversation starter questions to ask a guy.

1. What is your concept of a ‘good’ day?

What a guy values may be determined by how he would spend his ideal day. Also, depending on how he responds, you could receive some A+ date suggestions. For example, if his ideal day consists of a picnic followed by a live show, there you have it.

2. What is the most expensive item you’ve ever purchased for yourself?

This not only provides you with possible future present ideas if you get together, but it also gives you a glimpse into their spending habits. It might turn out to be useful information in the future. This is one of the random questions you can ask a guy that can spur conversation.

3. What is the thing most people get wrong about you?

This question will allow you both to go further. It teaches you about how the guy perceives himself and what he believes people see him as. Maybe he thinks they’re terrible jerks, yet they come off as bashful (or vice versa). It gives both of you a variety of areas to talk about.

4. What is your biggest achievement in life?

Men pride themselves on their achievements, as they get joy from talking about them. This question comes with lots of areas of interest in the guy. You may learn a lot about what’s relevant to him, whether it’s his work, school, family life, or relationships—there are many options here to explore.

5. What is the rule that you really love breaking?

Perhaps he likes to skip lines on long queues or break other rules. This question is not just to reveal the guy’s moral conscience, but it also helps you assess if it coincides with yours (which can seriously avoid future, potential problems).

6. What topics make you happy to talk about?

This is one of the random questions to ask a guy in order to start up a conversation with him. The question is not just a creative way to spice things up, but also a terrific way to dig into a guy’s interests. It’s always intriguing to hear someone speak about something they’re enthusiastic about because it gives you a peek at the kinds of things they find interesting.

7. What would you eat if you had to eat the same food every day for the rest of your life?

To begin with, chatting about food is always entertaining, and the conversation may even end with both of you being so hungry that you order something to eat. However, making a decision about eating a particular food for the rest of your life won’t be an eay one.

8. What would be the title of your behavior if it were a TV show?

This is much more entertaining and meaningful than just asking a guy what their favorite TV show is. This sheds some light on how they see their life’s narrative. Isn’t that profound?

9. What’s the worst date you’ve ever had?

If you want to smell out any warning signs (or, ideally, the absence of them), we recommend talking about terrible dates as a good place to start. This question is essential because it reveals what the guy perceives to be traits of a terrible date and, hence, a non-ideal mate. It also tells you what he believes is a nice date, the opposite.

10. What’s your favorite tale about your closest buddy to tell?

One of the simplest ways to persuade a guy to open up about himself is to have him speak about anything other than himself. This question tells you what the guy admires in other people. Also, we’re typically the replica of the company we keep, so you may infer the guy has acted in a predictable manner as their best buddy in their narrative or has at least applauded their actions.

Random Questions to Ask a Guy Over Text

The proper questions may really open the door to a deep, meaningful relationship. However, there is a significant difference between talking in person and texting. When texting, you can’t truly ask questions with replies that are lengthy, comprehensive tales or have a lot of complexity.

Texting is also not the best medium for having a serious or deep emotional discussion, since a lot may be misconstrued or lost in translation. As a result, it is the best medium for asking random questions to a guy. Below are some random questions to ask a guy over text.

11. What is your favorite website to spend time on?

This is a nice follow-up question. If he mentions YouTube, you may inquire about the sorts of videos he enjoys. You may even request his all-time favorite clips. Men like discussing their hobbies with women they admire, and they appreciate it when they see a real interest in the things they enjoy!

12. What would be the most embarrassing thing you’ve ever seen someone upload on social media?

This is one of the random questions you can ask a guy through text. He has probably seen some embarrassing posts on social media and would have a field day narrating it.

13. What is your immediate reaction when you get a phone call?

The response may be both informative and entertaining. Most of the time, we do have a reaction whenever we get a phone call, especially if it is unexpected.

14. What is it that you miss a lot about being a child?

This question may be a little more revealing without being too intrusive, so it’s ideal for asking a man you’re more at ease with. It’s also a good topic to ask in person since it may spark a lively discussion. Through text, this question can provide the opportunity to have other discussions.

15. What percentage of your time do you tend to spend on social media?

The question is one of the random questions you can ask a guy through text. In most cases, guys spend their leisure time on social media, except those who actually work on social media. This might pave the way for a larger conversation about social media and whether it is benefiting or harming our society.

16. What color is your phone’s background?

This is something he chooses and looks at on a daily basis, so it’s most likely relevant. Discovering what it is might reveal a lot about what he values. A guy’s phone background picture reveals a lot about what he likes the most. Most guys that are football lovers tend to have their best player’s image on the phone background.

17. What is always worthwhile in terms of packing calories?

This is a no-risk inquiry that is ideal for when you’re just getting started. You don’t want to start off on a heavy note, particularly if you’re messaging a guy you’re not dating yet or who you don’t know very well.

18. Which emoji best represents you?

This is one of the best random questions to ask a guy through a text message. This is a simple and adorable inquiry, but it may also reveal a lot about how he perceives himself. Everyone has an emoji that best describes them. Trying to find one that fits him is a good way of having a text conversation.

19. Have you ever sent an awkward text message by mistake?

Being able to openly share embarrassing situations with others is a terrific way to laugh and connect. If a man genuinely loves you, he’ll probably hold off on telling you about his really humiliating experiences and instead offer you something that doesn’t paint him in a poor light. The question can also help you know the extent to which he can be careless while texting.

20. Where is your favorite place to go on a date?

This is one of the random questions you can ask a guy through text and is a fantastic question to find out how romantic he is. Most guys have a favorite place where they like to chill out and have fun. Asking about his favorite relaxation spot through text is a good way of developing conversation.

Random Funny Questions to Ask a Guy

Funny questions put you in the best mood for a conversation. To lighten the mood of the guy you are having a conversation with, ask some funny questions. As much as it comes with elements of humor, make sure its informative aspects are not lost in the humor. Below are some random, funny questions to ask a guy during a conversation.

21. What’s a term you’ve spelled incorrectly your whole life?

This is one of the random, funny questions to ask a guy durinng a conversation. Taking a guy back to the spellings that gave him hard times as a child can be a funny way of communicating with him.

22. What is it that you believed as a child for far too long?

Did you ever think Santa was real? Share your amusing experiences with him and request his. Self-deprecating comedy often elicits laughter because it demonstrates self-awareness and is sympathetic. We may use nostalgia as a way to connect to a story from the past.

23. When you’re watching a fantastic TV program, how long do you wait to get up to pee?

A personal yet amusing inquiry can be disarming and will undoubtedly bring you two closer together. It is a known fact that some TV shows can have you pinned to one spot but what is his opinion on this?

24. What is the most disgusting food you’ve ever made?

The question allows him to express his bad cooking habits. Considering that cooking is not one of the biggest talents of most guys, the conversation is bound to get interesting.

25. What dominates your Spotify or Netflix accounts?

It’s tiresome to ask someone to name their favorite songs or movies. Instead of forcing someone to name their favorites just so you can pretend you know them, ask them what their Spotify/Netflix profile looks like.

26. What would be your best dad joke if you were a father?

Dad jokes are uncomfortable in any case, so you can both simply laugh and enjoy yourselves. Don’t forget to practice your joke beforehand so you don’t freeze in front of an audience.

27. Between being famous on TikTok and winning the Grammy Awards, which one would you choose?

Would you rather questions often lead to amusing conversations. These questions are an excellent way to find out what someone is interested in or other fascinating information about them that you may not have discovered otherwise.

28. What are your favorite and worst school photos?

It’s also a good idea to ask somebody to share a hilarious or embarrassing childhood memory. Most people look awful in their childhood photos, especially when you look at them several decades later. Taking him back to his childhood photos is a good way of achieving humor in a conversation.


When a discussion begins to stall, asking random questions might act as a burst of adrenaline. You may start lengthy talks with old friends or get to know people you’ve just met if you know the appropriate questions to ask. These random questions to ask a guy may be used for whichever reason you need them to be, so go ahead and strike up some fantastic discussions with a guy.


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