Random Questions to Ask a Guy - a List of Fun Random Questions for Dating and Speed Dating

Let's face it. The problem with most Random Questions to Ask a Guy lists is that they read like a list of job interview questions. The questions aren't really random. They're not even questions geared for just a guy. While questions like "What do you do for a living?" or "What are you looking for in a relationship?" are revealing, they're not really very fun or random when it comes to dating. With that in mind here are some truly random questions to ask a guy that aren't quite so straight-forward. Also included are links to some random questions for a guy lists that contain more basic questions of the "what's your favorite hobby" and "where do you see yourself in five years" variety. Remember, these random questions are just a fun way to get to know someone, and are not a substitute for honest, open communication.

The Random Questions to Ask a Guy List

1. What's the hardest thing you've ever done?

This random question reveals a lot about a guy. Both the answer and how he answers are revealing. Does he try a joke? Something like "Asking you out." Or does he answer the question seriously? "Getting over the death of a loved one." Either way you learn a lot.

2. If you were a car, what kind of car would you be?

Does he see himself as a fast sports car, an old classic pick up or a sturdy SUV? This random question can be fun.

3. If you were a city, what would you be?

This random question looks into a few aspects of a guy. Is he L.A. glitz? New York energy? Romantic Paris? Ancient Rome? Or small town USA?

4. If you were a movie, what would you be?

Would he be an action picture? A porn? A romantic comedy? Science-fiction? You can follow this up with, what actor would play you in the movie?

5. If you were a soup, what would you be?

I know. This one may sound kind of out there - but that's the point. Here you're looking at a guy's imagination and sense of humor. Will he go with the flow and answer the question or will he think it's weird? Either way, this random question reveals a guy's personality. Is he chicken noodle? Beef stew? Thick and chunky? Lentil? This one's mostly for fun.

6. If you were a tree, what would be carved in your trunk?

Another question that sounds kind of out there, but what did you expect - these are supposed to be random!

7. If you were sand, what would you say to people on your beach?

Have fun? Don't pollute? Use sunscreen! This is a chance for a guy to get creative and use his sense of humor.

8. If you were a house, what would you say to the people living inside you?

This random question is a bit more complicated than the one's before it, gauging humor, imagination and a guy's sense of home.

9. If you were a pebble, what would you say to a little kid throwing you into a pond?

Another opportunity for a fun question to get a random conversation going.

10. If you were an animal, what would you be?

This one's pretty easy for a guy. Just pick a cool animal and call it a day. The real key is the explanation. Be sure to ask the follow-up question: Why'd you pick that animal? Chances are he wouldn't have answered the question without already thinking of his explanation, which is what you're looking for with this one.

11. If you could travel through time and meet yourself when you were a kid, what would you say?

This random question deals with a number of issues. If a guy is money-oriented, he might say "I'd tell myself to buy Microsoft stock." Or he might do the whole "Back to the Future" sporting bets thing. This question deals with regrets and opportunities.

12. If a bartender named a drink after you, what would it be called? What would be in it?

This is another creativity and imagination kind of question that also looks into drinking patterns.

13. If you had to eliminate one thing in your life, what would it be?

A variation of the "If you were stranded on a desert island..." kind of questions.

14. If your house was on fire and you could only save one thing, what would it be?

Let him know that all his pets and loved ones are not in the house. Here you're looking at what material things a guy finds important.

15. What did you want to be when you were little and are you that now?

A little more roundabout way of asking about a guy's job and his attitude toward it.

16. If you could be any cartoon character, who would you be?

Would he be one of the Superfriends? Papa Smurf? Spongebob? Charlie Brown?

17. What do women like about you the most? The least?

This random question looks at how he thinks the opposite sex perceives him. On another level it also examines how he sees himself.

18. Should the guy always pay for a date?

This can be a hard question for a guy to answer . There's no clear-cut right or wrong response.

19. What would be the title of your autobiography?

Another random question more for fun. But then if his title is "No Regrets" or "Positive Impact" these are vastly different than "A Wasted Life."

20. If you had one superhero ability, what would it be?

This random question is mostly for fun but can be revealing. For example, the ability to fly is vastly different from the ability to see through anything but lead.

One thing to keep in mind is the old saying "Every question contains a power not found in the answer." What that means is simply - you can tell a lot about a guy by the questions he asks.

Remember the trick with many of these random questions lies in the answers. If a guy is into you, he may try to give you the answer he thinks you want to hear. That's easy to do with regular questions, but with more random questions, it's harder for a guy to figure out what answer you want, which makes them more revealing. Also remember that what is most revealing may not be the actual answer, but how he answers.

To read some more generic random questions to ask a guy, click HERE.

Be sure to add the best random questions you've asked your guy in the comments section below!