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Are you looking for something different, like a list of weird questions to ask a guy?

As an expert conversationalist, I have written articles about conversation starters featured on IHeartRadio and EliteDaily. I have great knowledge of how to start a conversation with a guy and funny conversation starters. You would want to make a lasting impression by being fun and random. We have the top weird questions to ask a guy and create that spark in your conversation.

Let's get started!

Contents

Top List - #Top-List

Top List

Printable List - #Printable-List

Printable List

How To Pick - #How-To-Pick

How To Pick

FAQs - #FAQs

FAQs

More Awesome Questions - #More-Awesome-Questions

More Awesome Questions

Top List of Weird Questions to Ask a Guy

A great conversation leaves a good memory. That is what we want, a lasting impression. Asking interesting questions will definitely create a different mood as the conversation will be more fun and random.

Question Categories

Strange - #Strange

Strange

Bizarre But Funny - #Bizarre-But-Funny

Bizarre But Funny

Absurd Yet Sexy - #Absurd-Yet-Sexy

Absurd Yet Sexy

Interesting Yet Peculiar - #Interesting-Yet-Peculiar

Interesting Yet Peculiar

Odd - #Odd

Odd

Uncanny But Personal - #Uncanny-But-Personal

Uncanny But Personal

5 Best Strange Things to Talk About With Him

Sometimes, we get tired of the typical conversation and want to add a little spice to it. But you have to be mindful not to ask awkward questions as it may ruin the mood of the conversation. Check our list of questions to ask a guy you like and have fun getting to know someone.

1. What piece of tech do you hope was invented in your lifetime?

He may have a unique idea that may be beneficial for everybody someday. The light bulb also came from an idea, and now, we use it everywhere. You might be talking to a future inventor here.

2. What fact do you wish you never learned?

This is an interesting question. I bet it will take some time to answer this. He will need to scour through his knowledge bank to find a fact he wishes never learned. For me, though, knowing is still better than not knowing.

3. Can you live without social media?

Almost everybody is on social media, and some people cannot live without it. Ask this personal question to know if he is the type of guy whose world doesn't revolve around his phone and prefers actual conversation.

4. What meal you wouldn't eat even for a million dollars?

You will get an interesting answer to this question. Is he that picky to refuse a million dollars? I know I could eat any meal for a million dollars.

5. Do you have your dream job?

If he has his dream job, that means he is the person who will pursue things. He wouldn't let obstacles get in the way of his goals. It is admirable if he already has his dream job. But if not, then it's not too late. Maybe you can give him the push and inspiration to achieve it.

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5 Bizarre But Funny Things To Ask Him

We want to have a great conversation, and being able to open up and communicate freely is one of the keys. Take a look at these funny questions and lighten up the mood of the evening.

6. Do you like having a beer belly?

Maybe guys want to drink beer, but most of us do not wish to have a beer belly. But I guess it can't be helped.

7. Have you seen your mom/sister/grandma naked?

If we could forget one memory, this is a good candidate.

8. Which celebrity do you have a crush on?

His celebrity crush is more than likely his dream girl or ideal woman. But it's only a crush; most of us have one. But you get the idea of his type.

9. Which comes first, egg or chicken?

This is a classic question. It will be a fun question to ask to see which one he thinks came first. You will have fun debating whether the egg or the chicken came first.

10. What is the color of your underwear right now?

Just a random question, but it will surprise him. This is a good way to start if you want to get to the flirty side.

5 Absurd Yet Sexy Topics To Ask a Man That Will Excite Him

Asking flirty questions is one way to tell a man how you feel about him without actually stating it. Get ideas for starting a conversation by checking out these sexy questions to ask your crush.

11. Do you wear anything to bed?

Does he want it breezy and cool or warm and cozy?

12. Are your parents as attractive as you?

This is the right question to ask if you want to tell a guy that he is handsome without being too direct.

13. Would you like to go on a date with me?

A woman who knows what she wants is sexy. The guy will more than likely say yes.

14. If you were a cop, would you detain me right here, right now?

This is another way of asking if he is enjoying himself with you. As long as there are no real cops involved, all is good.

15. What makes you, you?

Let him talk about the traits that he likes about himself. Top it with compliments, and he will surely melt.

5 Interesting Yet Peculiar Topics To Talk About With A Guy

Good questions are necessary to keep the conversation going. Look at our list of interesting questions to ask a guy, and there won't be a dull moment between you two.

16. Who is your hero?

This is a great question to ask to know someone deeper. He will tell you an important piece of his life. This is a good conversation starter because you get him to open up to you.

17. Do you have any favorite colors?

A very basic question to ask. Google the meaning of each color. This will be a fun conversation when you tell him the meaning of his favorite color.

18. Are you more into looks or brains?

A deep question that reveals if he gives more importance to what's inside or outside.

19. If you were to marry a celebrity right now, who would it be?

It will reveal his type in a woman. He must like her very much if he is willing to marry this celebrity. But no worries, wishful thinking is different from reality. Besides, it is you he is with right now.

20. Would you rather have fame or money?

Can I have both? Just kidding! No matter what he picks, the reason for choosing that answer is what matters. Hear him out.

4 Odd Things To Interrogate a Man Over Text

Not being together is not a reason not to get into the conversation. Read through the list of questions to ask a guy over text and have him hooked to your discussion.

21. How many phones have you broken or lost?

This tells you how careful he is with his belongings. If he has broken or lost too many phones in a couple of years, that means something.

22. Do you have any interesting trivia that you know?

Most women like witty guys. I mean, that trait impresses some women other than looks. If your guy knows a trivia or a fun fact, that is one brownie point added to the basket.

23. What has a neck but no head?

This question will get him thinking, and he could think of the craziest thing for an answer, which is the fun part. If you don't know the answer, you can search it online. (Hint: you are probably wearing it right now).

24. Have you taken a bath right now?

This could be a weird question to ask a guy for some. But, she is just checking, making sure that you take care of yourself. There is no harm with that.

4 Uncanny But Personal Things To Talk About With a Man

We want the person we are talking to be able to open up to us. All you need is a list of questions to ask a guy to get to know him. Shoot these personal questions to ask a guy to get to know him deeper.

25. How many girls' numbers do you have on your phone?

You can tell based on his answer if he is a bit 'too friendly' with women.

26. Do you usually stay friends with your exes even if you have a girlfriend?

If he stays friends with his exes, the breakup was not bad, and they respect their past relationship. But it is up to you if you like the answer or not. Some women prefer to leave the past behind completely.

27. Do you think you are ready to get married?

That is the big question. Is he ready for a lifetime commitment and responsibility, or is he still playing? Knowing if you are on the same page is important before you get into a relationship.

28. When was the last time you cried?

This is a good question with a more serious tone. Opening up may not be easy for anybody. If he does, that means he is comfortable sharing his life stories with you.

Downloadable and Printable List of Weird Questions To Ask A Guy

Here is a downloadable and printable list of weird questions to ask a guy (right-click the image and select Save Image As...):

How To Pick The Best Weird Yet Worthy Questions To Ask A Guy

There are many questions out there for you to ask. But you need to know the appropriate questions to ask to keep the conversation comfortable for both of you. We provided tips to guide you on picking the best weird questions to ask a guy.

1. Start with Lighter Questions

This is to test the waters. See how he responds to lighter or more basic questions so he can open up and feel comfortable. If you sense that he is not really into answering weird questions, switch to basic and more common questions. You want the other person to feel comfortable talking to you so he can share more.

2. Ask Questions That You Are Also Willing to Answer

Expect that he will ask you the same question. This is when he asks, 'how about you?'. Pick the question that you know you will be comfortable answering because, more than likely, he will shoot the same question to you.

3. Trust your Instinct

The whole point of having a conversation is to enjoy yourselves while knowing each other. Your heart will tell you if you're asking the right questions based on the other person's responses. Trust your instinct and let it guide you in picking the right questions. Go with the flow!

Frequently Asked Questions

Have a fun and interesting conversation by asking the right questions. Avoid uncomfortable questions as they might set off the ambiance. We will ensure that you don't make this mistake, and we are here to answer your questions.

What are some awkward topics to ask a guy on a date?

Beware of these questions, ladies; Are you over your ex? Who was your prettiest or hottest ex-girlfriend? Have you ever cheated on someone? What makes you insecure?

Avoid asking these questions. Do not dig into his past relationships. Talk about what's in the present. Don't make him feel bad about himself by asking what makes him insecure. Keep it fun and appropriate, so he gets to talk more than avoid your questions.

What are questions to ask to get to know someone you like?

Ask questions that will make him open up to you. Questions that will ask him to tell something about his experiences and preference. Examples are; How do you spend your day off? What makes you excited? What is your favorite drink? What is your favorite movie genre?

You will learn a lot about him by asking some of these open-ended questions. The answers will also reveal if you are compatible or not.

How to ask a shy guy for a date?

There is nothing wrong with a woman making the first move. It might be an admirable trait for some. Read through how to ask a guy out, and it will guide you on the best practices for asking a shy guy for a date.

Do guys like being asked weird things?

I cannot say yes for everyone, but most guys prefer unique and interesting questions. But there are appropriate weird questions to ask a guy. These questions are random and unique, but they are not uncomfortable questions.

More Awesome Questions To Start A Conversation With A Guy

If you do not feel like asking weird questions, then we still have you covered. Check out these awesome lists of questions to ask a guy to spark that conversation.

  1. Don't know how to approach someone? Check out these cute things to tell to your crush to keep that conversation going.
  2. Shoot these questions to ask your boyfriend and get to know him deeper.
  3. Congratulations on finding the right person! Now both of you try answering these questions for a new relationship to build intimacy.

In Conclusion

Be the one that breaks the cycle and be fun and random. You will most likely leave an impression with this list of weird questions to ask a guy.

Do not overthink too much of what you're going to ask, as what's important is for both of you to enjoy your time together. So go with the tides and see where it leads you. Now get out there and have an interesting night with someone.