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Weird questions to ask a guy

Now when someone is looking for weird questions to ask a guy, well that can mean a lot of things. These questions lean towards the random and strange. So hopefully that is what you are looking for when you are looking for weird and not the 4chan type of weird.

You can also have a look at weird questions to ask a girl, weird questions to ask your friends, or you can check out these weird conversation starters.

List of weird questions to ask a guy

You can browse through the questions below to see what works for you. Like I mentioned before, a lot of these questions are a bit random and some are a little bit strange, but all of them are quite varied. So you should be able to find at least a few weird questions to ask a guy that will work for the guy you are asking.

1. What’s your fast food horror story?

We’ve all got one. The guy you’re asking will too. Probably more than one. Plus there are so many urban myths around fast food, you’ll have plenty to talk about.

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

Most guys are into games. Whether it’s sports, video games, or board games, the guy you are talking to will probably like at least one of those types of games.

So with this slightly random question you can learn a lot about what he likes. Also you can give him a little room to brag as well.

3. What scene from a movie scarred you for life?

Let’s face it, we’ve all seen something in a movie that has stayed with us ever since. Whether it’s American History X or Grave of the Fireflies, we’ve all been scarred at one point or another with a scene from a movie.

4. What’s the most important file on your computer?

I like this one a lot too because you can sometimes get some really interesting answers. Of course it might be a super boring answer, but who knows? You might get something really unexpected.

5. What is your hometown best known for?

There’s something that sticks out about everyone’s hometown. And whether you share the same hometown with the guy you are talking to or not, this question is sure to get you both talking and reminiscing about the past.

6. What’s the future of dating?

This one is a bit out of left field. But it could be interesting depending on how into scifi and future stuff the guy is. Give it a shot, you might get an interesting answer!

7. What, besides wealth, do you never have enough of?

What does your guy want? Well, you are about to find out. This is an interesting one because you can get a lot of varied and interesting answers.

8. What’s something you’ve done that you would try to dissuade anyone from doing?

How about some embarrassment? Find out something incredibly stupid that your guy did. But remember, you should be nice and tell him one of your stories of you doing something stupid as well.

9. What is the longest amount of time you have been awake?

There’s probably a good story behind why he was awake. I mean, no one stays up for days just out of boredom. Plus, people get a bit loopy after being up for a long time, so probably there are some funny stories in there too.

10. What would be the most spectacular funeral you could imagine?

You’ll find out how creative your guy is with this one. You can have a surprising amount of fun imagining your own awesome funeral. Sure you won’t be there to enjoy it but that’s no reason for it to be boring!

11. How often does your brain go on autopilot?

You know, when you are doing something you’ve done a thousand times before and you just kind of zone out. Then, BAM you are slammed back into reality and you wonder how you got there or if you just finished something or were just starting the thing you were doing.

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

Once you learn something, often times it’s hard to unlearn. Although in the case of studying for a test, it can be surprisingly easy. Still this question can definitely lead to some interesting and creative answers.

13. What board game always ends badly?

Oh board games. You bring families together and then tear them apart. It just seems that some board games are designed for rage quits.

14. When did the saying “looks can be deceiving” really hit home?

I love this question because there isn’t really any way to predict what answer is coming. There are so many ways to apply the saying that there is a huge range of answers.

Although, if he has a rough romantic past, you might be hearing about an ex-girlfriend.

15. What landmark from your childhood was destroyed and what was put up in its place?

This one’s not super weird, but pretty uncommon. There’s a good chance that neither of you have ever been asked this question before. Plus, I can guarantee you both have an answer to this one. It’s a pretty universal experience.

16. What would you do if you woke up tomorrow and it was 13 years in the past and you were your younger self but still had your current memories and experiences?

It’s always fun to imagine what you would do differently if you could. With this question you’ll be able to find what he regrets or what opportunities he thinks he missed.

17. What is the most useful thing your mom or dad has taught you?

A great question for getting to know him a little bit better. You can find out more about his parents and what he thinks is worthwhile. And maybe learn something that you didn’t know he could do.

18. What fun activity from your childhood has been completely ruined for kids today?

This question is a lot of fun, because how children are raised changes so quickly that there are tons of answers to this one. Plus you both get to reminisce about your childhood and what you enjoyed about it.

19. What piece of tech do you hope is invented in your lifetime?

Another one that is a lot of fun to discuss. There are so many to choose from in science fiction and your own imagination. And who doesn’t like thinking about the world of tomorrow and how awesome it’s going to be?

20. What’s your best example of a pyrrhic victory that happened to you?

Definitely an uncommon question. And there is sure to be an interesting answer to go with it. Hey, you wanted weird questions right?

21. What old fashioned way of doing things is better than how they are currently done?

Time to break out the “back in my day…” stories! Or maybe he’s just are fed up with how things currently are and wants to return to a bygone era that he didn’t actually live through. Either way, a lot of things are better now; but lets face it, some are worse.

22. What are some things that you haven’t seen or read, but know everything about because of popular culture?

Whether it’s the plot of a book or movie, you’ve probably heard so much about something that you feel like you’ve already seen it. Well time to find out what he hasn’t seen or read yet.

23. What is the most boring activity imaginable?

Get creative with this one. Sure you can go with the mundane boring stuff. But try to press him to come up with something uniquely boring, something off the wall.

24. What’s your most impressive “go to” meal that you can cook?

What can he cook? Time to find out! And maybe even get some delicious food as well, if you can convince him to cook you his signature meal.

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

More cool future tech stuff. Because most guys love cool future tech stuff. So why not? Cyborg up and see where the conversation takes you.

Well that’s all the weird questions to ask a guy that I’ve got for you. But there are a ton of other questions on the site, you should be able to find all the questions you need!

More questions to ask a guy

If you are looking for lots more questions, check out our main questions to ask a guy page or have a look at these: