20 Questions To Ask A Guy

20 Questions to Ask a Guy

Welcome to 20 Questions to Ask a Guy. We think it is important not to ask too many questions that the guy would have heard before. Remember, people judge you by the questions you ask, not just the answers you give, so having some great questions to ask a guy will go a long way. These 20 questions to ask a guy will help keep the conversation more interesting and help build rapport. Consider it your cheat sheet!

Down the page is some information to help you to become a master of this fine art! Some people call it the Master Class for women who want to know exactly what a man wants.

These 20 questions to ask a guy are questions for getting to know him better, be it on a first date, or at a social gathering or similar. You might not get the chance to ask every question, and you might want to change the order around to suit you.

20 Questions to Ask a Guy

1. Do you have a favorite movie?
One of us used to get asked “What is your favorite movie?” a lot, and sometimes felt embarrassed admitting that he didn’t have one. Changing the questions a little to “Do you have..” takes the pressure off, but allows the guy to tell you about his favorite movie if he has one.

2. Do you have a favorite author?
Same as the above but for further insight.

3. Do you have any pets?
This one is obviously not particularly original and that’s fine, it gives him an opportunity to talk about his pets if he has them, and if not, you can quickly move onto another question. Guys like being given the opportunity to talk about their things and what they like without sounding like they are bragging, so pets are always good for that.

4. How often do you go out? Where do you like to go?
This is obviously good for finding out what sort of person he is, but it also gives an opportunity for you two to build rapport or find something in common, he will most likely ask you the same question, so it can be quite a long talking point.

5. Spotlight, Audience, Or Backstage?
As well as giving insight into his character, this makes for a slightly more interesting question that he might not have heard recently.

6. Beach Or Mountain?
Maybe you can plan your first outing together, or maybe just add a little fun to the conversation by add some quickfire A or B questions.

7. Weirdest Christmas Gift Ever?
Of course, being reminded of past Christmases and childhood helps to bring emotions into the conversation and build rapport, as well as making for some interesting conversation.

8. What is the craziest thing you have ever done?
You might want to wait until more of a connection between the two of you is made, then again, this question could be the one to move you into more intimate conversation. It isn’t unreasonable to be asked this question, but be prepared to answer it yourself!

9. Tell me a funny childhood story
Humor and memories are a good combination and getting him to open up about some funny things in his past is a good way to make you both feel relaxed.

10. If you could kill five people in the world, who would they be?
Questions like this are lighthearted and allow for a lot of follow-up conversation, as long as you aren’t one of the five people he mentions.

Read on for the last 10 of 20 Questions to Ask a Guy

11. What did you want to be when you were 10?
You could choose any age really, but most people wanted to be something outrageous at that age, so it should make things more interesting, without bringing his possible regret at not achieving his dreams into the equation.

12. What was your favorite Halloween costume and why?
No real reason behind this question, it is just fun.

13. If you could have dinner with any three people from any time, fictional or non-fictional, who would they be and why?
Similar to the five people you would kill question, it can set up for nice follow-on conversation and is also insightful into a person’s character.

14. What made you laugh the hardest in your entire life?
Laughter and memories are good remember?

15. If you were a waiter and a couple were being rude would you spit on their food?
This one is obviously just a bit of fun (maybe) but can be quite topical if you are in a restaurant at the time. Give the waiter suspicious looks to add to that “in-joke” dynamic.

16. What’s the worst lie you ever told? Did you get caught?
Of course you might not get told the “worst” lie, but it adds more rapport and connection to the conversation.

17. Do you have any talents?
Everyone is good at something, you never know what it is unless you ask. This can also build trust quite well.

18. What’s the one skill/thing you would learn, if you could?
Ambition, dreams, people like being asked about them without having to bring the conversation up themselves.

19. If you could wake up anywhere in the world tomorrow, where would it be?
This is a personal favorite of mine because you can learn a lot about somebody from their answer, it is also a nice fun question!

20. What do you want out of life?
This one could be quite general and some people might not know how to, or want to, answer, but I put it out there as it can be very insightful and help develop trust.

Master Class in Communicating with Guys

As you master these 20 questions to ask a guy, you will want to get better at communicating with your guy, using both verbal and non-verbal language. Some call it the Master Class for women who want to know exactly what a man wants when he says “talk dirty to me”, for even the nicest girls to make a man addicted to you without even touching him, for those women who want to master their craft.

To learn the language of desire, to master the art click here or on the image below to find out more.
20 Questions to ask a guy

Beyond these 20 questions to ask a guy, check out more questions, below:

As always, if these 20 questions to ask a guy have spurred some suggestions for categories, or you would like to contribute your own questions, feel free to contact us.

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17 Comments

  1. Some good openers here for anyone.
    Thanks

  2. That is a classic picture! Sit on that chair and get interrogated – hee hee.

  3. Well they are some questions for sure on the spot is their a light that goes with this type of questioning…I am sweating already…..LOL just kidding these would break the barrier maybe a important question left out……# have you ever been in jail and if yes for what….just thinking out loud…:)

  4. Some of these sound like good ice breakers, but wouldn’t you feel kinda put on the spot with some of the more complex ones? For example I thought about how I might answer a few, like 3 people to eat dinner with, for example and I think if I was really interested in the girl, trying to answer would put me in a bit of a sweat. Is that just me?

  5. This is a grate list of question to fire at guys. Nice one 🙂

  6. “If you could kill five people in the world, who would they be?” Haha, I think if someone asked me that I would probably think there was something wrong with them. It’s a great list though!

    • Ask Them Questions

      I had someone tell me that question was a bit inappropriate and not nice content, which is probably true. It was intended to be a light hearted joke question, but I’m starting to think it might lead to people being offended

  7. Some great conversation openers here, I don’t think it would be a case of asking all on one night but hopefully over a few dinners!

  8. Hi there! I just wish to give you a huge thumbs up for your excellent info you have right hre
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