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25 Weird Questions To Ask A Guy

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You see him from across a crowded room. You would like to talk (maybe) to him. But, what exactly should you say? You could start off with something lame, like “Do you come here often?” He may or may not appreciate the awkwardness of that question. Or even cheesier you could ask “Do I know you? You look a lot like my next boyfriend.”

Most people may be put off by that one! You probably want to make a good first impression – not come off as some crazy woman! You know what they say, you don’t get a second chance to make a first impression – so you need to come off as a normal, well-adjusted person if you have any hopes for a conversation (or more).

Below you will find a list of random questions that can start a conversation with a guy. Some of the questions are deep and philosophical, others are more light-hearted and fun. Pick out a couple you like and have them ready the next time you see that guy off in the distance and want to talk to him. weird questions ask guy

1. Do you have a fast food horror story?

Who doesn’t?! This will give you both a lot to talk (and laugh) about.

2. What is the most spectacular funeral you can imagine?

So, this one is a little out there, and you may not want this to be the first question you ask a guy! But, after you get to know someone a little better, this question could let you know how creative they are!

3. What is one thing you have done you would not let someone else do?



This question may tell you just how much of a risk taker he is – which may be a good or bad thing!

4. Where do you see yourself in five years?

You may want to save this one, it probably isn’t’ a great first-time conversation question. But, it will tell you if he has goals for his life.

5. What is your dream vacation?

You can get creative with this question. Make it so that money isn’t a thing. You can go anywhere, anytime, and stay for as long as you want! Maybe you want to go on a tour of the world!

6. What is one thing you would like to try but are too scared?

He may not ever admit he is too scared to do something, but most people haven’t tried something out of fear. You can learn a lot about a person if they are willing to admit their fears.



7. What is something you would like to change about yourself?

This could be a tough one if you are being sincere and honest. But, it doesn’t have to be a personality flaw you want to change. You could phrase it so they could change their eye color or height or something more fun. The last thing you want to do is scare him away with a profound question!

8. What is the most embarrassing thing you have ever experienced?

This could be a hoot! We have all done something or been through something that was really embarrassing. Open up and share these stories to get closer without being too serious.

9. What motivates you most in life?

Everyone is driven by something. Some people want to make money, other people just want to be happy. Find out and learn about his desires.

10. What did you want to be when you were a child?

Most of us dreamed of being something as a kid – a doctor, a trash man, or a fireman. See what he wanted to be and ask whatever happened to that dream as a follow-up question.

11. Is your hometown famous for something?

Everyone has a fond memory of the town they grew up in. Asking this question will bring back some happy memories and may even a few stories he can tell you about.

12. What is the most boring thing you can think of?

We all know of some pretty boring activities. You can even get creative with this question and make up things! Try and think of something very off the wall and get a good chuckle out of it!

13. What is the most important lesson your parents taught you?

Our parents taught us more about life than realize. This question may make him think for a while. But, it will let you know what kind of a relationship he had/has with his family and how much respect he has for what they taught him.

14. Who is your celebrity crush? Why?

If he blushes when you ask this and hesitates, he may or may not be willing to tell you the truth! But, this could be a fun one to ask and see what traits he finds attractive.

15. What is your idea of the perfect day?

How he spends his free time and what he considers a ‘perfect’ day are good things to keep in mind if you two hit it off and go on a date. You can keep this information tucked away and plan a special day just for the two of you!

16. What sport are you best at?

Most guys love to play sports (or they did). Asking a guy about a sport may bring out the macho side. But, he may also have been a really good athlete in his past and would love to share his achievements without sounding like he is bragging. Depending on what he says, you may also find out if he thinks he is a super athlete or not

17. What is your favorite book?

If reading is important to you, you may appreciate a guy who likes to read too. There are men out there who do like to read – and they will read more than gun, boat, and car magazines! Real men read books!

18. If you got stranded on a desert island, what one item would you be lost without?

This answer may go through several rounds. You may pick an item, then think about it a little more and change your mind. Let us be honest, there are many, many things most of us couldn’t live without if we got stranded on an island!

19. If you could have one superpower – what would you choose?

Super strength, super speed, invisibility, or the ability to fly? The options are really quite endless! After you ask this question, you can tell him your superpower wish and see who would be a better superhero!

20. Cats or dogs?

This simple question may need to be repeated. Not a lot of people would get that you are asking a question! Hopefully, if you are a cat-person, the guy you are interested in is also a cat-person. It would just make the future a little easier. But, there is nothing wrong with falling for a guy who loves dogs (if you are a cat-person). Compromises can be made!

21. If you won the lottery, what would you do with the money?

Well, the idea of having millions and millions of dollars at your disposal can bring out some pretty crazy shopping trips! Have fun with this one too, he should be able to pick out some outlandish item to buy! It will be interesting to see what he would want to have.

22. Who is your hero?

The person you choose can be dead or alive, famous or not. The person this guy looks up to can tell you a lot about him! If he sees a famous athlete as his hero, you can tell where his priorities lie. If he tells you that a serial killer is his hero – head for the door!

23. What is your biggest regret in life?

Most people regret something. Maybe they didn’t finish school or took a job that they really wish they hadn’t. Opening up to someone about a regret takes strength and may not be easy to admit.

24. Do you have a dream job?

Maybe he already has that dream job! If he doesn’t, you can ask him what it would take to get that dream job, it would show you care and were listening.

25. What is the most challenging thing you have ever faced?

This could get you a serious answer, so be prepared for reality. This might be a good second or third date question.

There you have it, a list of 25 conversation starters for you to use on a guy. You don’t have to use them on a stranger – you can ask your boyfriend or husband these questions too. Asking someone you have known for a while where they see themselves in five years could be fun (or not)! Be prepared to have to answer them in return though! Most people won’t be willing to just spill the beans about personal stuff without something in return. Communication is essential in any relationship, keep talking, keep sharing!

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