40 Fun and Weird Questions to Ask a Guy

They say men are simple and women are complicated. But that’s not always true. Sometimes, penetrating into the brain of a man can be a difficult task—maybe even a challenge. Women sometimes resort to various tactics, all just so they understand what’s happening and what’s going on inside the brain of their partner. But to be fair, the simplest way is to ask. That being said, let’s take a look at several questions to ask a guy.

Keep these questions in the back of your head at the beginning of the relationship. You’ll get a much better understanding of the man you’re dating, and where your relationship might end up.

1. What are your personal goals?

This is definitely one of the most important questions to ask a guy. At the beginning, you want to know what your partner’s goals are. If you don’t have the same personal and life goals, chances are your relationship won’t last.

2. What kind of childhood did you have?

The past is what makes us who we are. Once you understand your partner’s childhood, you’ll have an easier time understanding his motives today. You want to know why he is who he is. It’s one of the “must ask” questions to ask a guy you like.

3. What fact do you wish you had never learned?

When you learn something, it’s hard to unlearn it. In the case of studying for a test, you want to remember everything. But sometimes, we find out things that we don’t want to know. For example, a few years ago a friend of mine told me that “female kangaroos have three vaginas.” I did not need to know that.

4. What do you never have enough of?

Do you want to know what your guy likes? Well, all you need to do is ask. I’m sure he’ll come up with some interesting answers.

5. Do you like to read?

Personally, I would rarely date a guy who doesn’t love to read. Given the fact that I love reading, I want someone who will share some of my interests. Of course, it doesn’t have to be “a must.” But if he likes to read, you can get into cozy discussions about books you like and dislike.

6. What job you would like to have?

Once a man starts talking about work, it can get boring. To be fair, not many people want to talk about work. But this is a situation in which you talk about something that he would like to have. And we all have hidden desires. The way he talks about work will show you his work ethic and motivation.

7. What qualities do you look for in a girlfriend?

If you notice that the two of you can have an open discussion, this is a very good question to ask. You’ll be able to find out what drives him crazy. You can even tease him if you possess some of the qualities he looks for. In any case, his answers will give you clues as to whether you two are good together or not.

8. What are you afraid of?

For example, I’m afraid of the dentist. We all have fears, and they are all different. I know people who are afraid of the dark. The goal here is to find out his fears so that you don’t make him afraid accidentally.

9. What makes you insecure?

Very similar to the previous question, but with a slight difference. Sometimes we are afraid of something, but that doesn’t make us insecure. The goal here is to find out why and when your guy feels insecure so that you can deal with the problem at the critical moment.

10. Do you want children?

This is as straightforward a question as it can be. I don’t recommend asking just any guy this one since some are not as open as others. But if you sense the conversation is going in the right direction, you can throw it out there. After all, talking about children and the relationship is crucial for a happy relationship. Just try not to panic your partner with the question.

11. What’s something embarrassing that you did that you want to forget?

We all have embarrassing stories. And they are usually funny and comical. Just be nice and tell some of your stories as well. You don’t want to make your guy look silly and incredibly stupid.

12. What do you think about the saying, “Looks can be deceiving”?

This is one of those questions for which there is no right answer; you’ll hit a nerve for sure. Some guys will play it cool, and others will just say that looks are everything. But it will be a worthy discussion.

13. What’s your family like?

Men are more connected to their family than women. Although, I know a few girls who are practically glued to their family. But men are the ones who are usually very connected to their mother. In any case, he will love the fact that you take the initiative to get to know the people he loves and likes.

14. What do you pride yourself on?

We all have something special about ourselves that we take pride in. Whether he will answer about his talents, personality, or even looks, you will engage him in a conversation that shows interest. You want to get to know him. Pride is something you must be aware of.

15. Have you ever cried at a movie?

Most guys will tell you no, even if they have cried at a movie. We all know that women appreciate a sensitive guy. And to be fair, there are some movies where you just can’t stop the tears from flowing.

16. What expectations do you have of yourself?

What he expects from himself is the same he expects from you. You can be sure of that. Therefore, find out what he expects and what awaits you.

17. What are your professional goals?

I told you that one of the best questions to ask a guy is about his personal goals. But don’t forget his professional goals as well. They are different. You want to know if he is planning to move up in his career, or if he is satisfied with what he has right now. Some women appreciate ambitious men, some don’t. And let’s be honest: the success of the relationship can be more difficult if both of you are extremely ambitious in your careers.

18. If you could go to any place in the world, where you go and why?

Traveling is a huge part of the relationship. We live in an era of relatively easy travel, and we all like to explore different parts of the world. This is just one of those “get to know him” questions. Who knows, maybe you both dream of the same place?

19. What’s your favorite sport to watch or play?

Guys love talking about sports. That’s one topic that will definitely keep the conversation flowing. You can retain some of the knowledge, and you might even get invited to watch a game. Again, this is a question that shows your interest in his hobbies.

20. What game do you dominate when you play it?

Games are another topic that get the conversation going. You can expect a sports answer again. But some men excel at video games, some playing board games. And chances are your guy will love at least one of these. It sounds like a random question, but it will help you find out what your guy likes. And you will give him some wiggle room to brag. We know men love to brag.

21. What movie scene has scarred you for life?

We all have witnessed a movie scene that left us scarred for life. For me, it’s the elevator scene from Grudge. Ask your guy what his scene is.

22. What’s your hometown known for?

We all take pride in the place we come from. Maybe you share the same hometown, maybe not. But there is something that sticks out about our hometown. Both of you will certainly talk a lot on the topic and reminisce about past events.

23. What’s your favorite car?

Cars are another topic that guys love talking about. Bonus points if he is a car lover. He will definitely appreciate the fact you asked this question.

24. What’s your favorite food?

Pizza doesn’t count. Or burgers. Just kidding. Men love to eat, and they are usually the ones who can’t get enough food. And let’s be honest: the better you get to know him and his favorite foods, the better your relationship will be.

25. What would do if you had a million dollars?

Do you have an answer for this question? If someone asked me this question, it would take me some time to consider the possible answers. But off the top of my head, I would like to go to Italy. This question really brings out the adventurous spirit of your guy. Or his entrepreneurial spirit. You might expect an answer like, “I would invest the money in so and so.”

26. What’s the worst thing you’ve done?

Yes, this is a weird question. And we had a similar one before. But the topic is fun and will reveal some interesting facts.

27. Where would you like to move?

The goal here is to determine whether your guy is an urban guy or not. Some like to live in a metropolis, while others enjoy a house in the suburbs with a garden. In both cases, you’ll understand more about the guy you’re dating.

28. What’s the go-to meal you cook to impress someone?

Does he even cook? Well, if he cooks some delicious food, you can be sure you’re in for a treat. If he jumps at the opportunity to cook for you, that’s a good thing.

29. What part of your body would you replace with an improved mechanical version?

Yes, this is a bit of a sci-fi question. But cool, future tech questions are fun. You can always speculate and talk about cyborg things. You don’t know where the conversation will take you!

30. What’s the most useful thing your parents taught you?

This is one of the best questions to ask a guy to get to know him a little better. You’ll find out a little more about his relationship with his parents. And you’ll find out what morals they installed in him.

31. What makes you smile?

This is a simple, yet very useful, question. It shows you’re curious to see what makes him happy. You can definitely use that in the future to make him happy!

32. What’s your favorite movie?

Another question that will help you determine whether you have common interests or not. Talking about movies always keeps the conversation going.

33. If you could describe yourself with one word, which would it be?

Yes, it sounds like a question people ask at interviews. But that’s the beauty of it. Pay attention to the word he uses. Usually, short words and answers are characteristic of fast, skilled guys. If he takes a long time to find an answer, he must have never thought about himself.

34. What kind of animals do you love?

You can ask this as “Are you a cat or a dog person?” Usually, those are the two answers you get. And don’t underestimate the answer to this question. A person who doesn’t love animals can’t love people.

35. How often does your brain go on autopilot?

Men often zone out when they talk to their girlfriends. It’s a fun way to understand whether he zones out, and how he does it.

36. What’s the craziest thing that you’ve done?

We had a “most embarrassing thing” question, and now we get to the crazy part. One thing is certain: you’ll get a glimpse of his past. But you’ll also get a sense of his boundaries.

37. Who is your biggest hero?

You want to know who your guy looks up to. Some look up to superheroes, some to regular people. We all have our idols, and it’s important to know who that idol is.

39. What’s your favorite time of the year?

Is he a summer person, or is he a winter person? There are differences. Some love to go to the beach and swim, while others are more of a “skiing on the mountains” person. You can bond over what you both like.

40. Are women equal to men?

This is one of those questions that you absolutely must ask. You want to know how your partner views equality between the sexes.

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