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21 Questions To Ask a Guy

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Have you ever seen a guy you like on the street, in a coffee shop, or even in the office? If so, have you ever pondered on the best way to start a conversation with him? We all have our shy moments and no one wants to experience an awkward silence for asking the wrong question or just saying the wrong thing.

So how do you start a conversation without looking awkward or saying something cheesy? Whether you have a budding romantic interest in someone or you just want to get to know a person a little better, read on to see a list of 21 questions to ask a guy that will help you start a conversation in a fun and casual way.

Related: 10 Beautiful Love Quotes for him or her

21 Question to Ask a Guy

21 Questions To Ask a Guy

  1. What type of food do you like?21 Questions to Ask a Guy - Food
    They say: “The way to a man’s heart is through his stomach.” I would argue that’s also the way to a woman’s heart. In either case, a discussion about your favorite foods is sure to unravel an exiting conversation. You never know, this could even lead to a romantic dinner date.
  2. What kind of music do you like listening to?
    21 Questions to ask a guyDid you know that your taste in music says a lot about your personality? Adrian North, PhD, a music psychology scholar, conducted a study on more than 36,000 participants, to learn how music preferences can predict your personality. Sharing a conversation about your favorite type of music is a fun way to find common areas of interest.
  3. What would you do if you won a million dollars?21 Questions to Ask a Guy Lottery
    Who doesn’t like to fantasize about having millions to spend on anything they want? For many of us, the first order of business may be paying off loans. But after doing some financial house cleaning, this is could lead to a really fun discussion on things that matter most to you and to your prospective love interest.
  4. Do you like pets?21 Questions to Ask a Guy - PetsI’m a pet lover myself, but not everyone is. Talking about your experiences with pets, whether they’re good or bad, could unravel the most fun conversation about your encounters with pets. Like this one time, I was in the service elevator to take my two Shi-Tzus out for a late night walk. As soon as the elevator door opened and my two Shi-Tzus darted out, they scared the bejesus out of a person that didn’t expect to see two hipper little furballs coming out of the elevator.
  5. What is your dream job?
    21 Questions to Ask a GuyWhat if going to work took on a whole other meaning? Do you dream about working freely on your laptop from a remote location? Or maybe from your local coffee shop, bopping your head to your favorite beats? Asking the question what is your dream job is sure to reveal interesting likes and dislikes.
  6. What’s your favorite hobby?
    21 Questions to Ask a Guy - HobbyWhat do you like to do in your spare time? There are many hobbies that you can talk about when trying to know someone a little better. Maybe you like jewelry making, knitting, photography, or maybe shopping? Having a conversation about favorite hobbies could even be an occasion to set your next date at a group pottery or drawing class.
  7. Do you like traveling?
    21 Questions to Ask a Guy - TravelI personally believe that traveling can be a great way to discover new cultures, foods, music, languages, and a way of life that is different from the one you know. Have you ever been to an exotic Caribbean destination, a Kenyan safari, seen the Eiffel tower, or roomed through a buzzing open market or ‘souk’ in Marrakesh? Or maybe you would like to set out and discover the world. Either way, why not try to start a conversation by asking a guy if he likes traveling and sharing your experiences with traveling, airports, or even how to find the best travel deals.
  8. Do you like sports? If so, what are some of your favorite sports?
    21 Questions to Ask a Guy - SportsI personally don’t follow sports but I always enjoy how passionate people can be when they talk about their favorite football, basketball or any other sports team. If the guy you meet is a sports fan, questions about his favorite sports is sure to start things off on an exciting note.
  9. What’s your favorite drink?21 Questions to Ask a guy 23I grew up in Belgium which is country known for its chocolate, waffles, and also its beers. And when I go out with friends, I always enjoy ordering a nice cold beer. More specifically, Belgian beers like Stella, Duvel, Lambic and many others. If you want to learn more about Belgian beers, check out ‘A Guide to Belgian Beer Styles’ by Dave Jensen.
  10. Do you like cooking? If so, what do you like to cook?21 Questions to Ask a guy 22There are days when I’m really into cooking and when I enjoy whipping up a fabulous lasagna, a savory quiche, or a delicious Nutella cheesecake. Wouldn’t it be fun to discover your love interest’s favorite recipes? Maybe you can even take a cooking class together and learn some new recipes, while you casually get to know each other better.
  11. Do you believe in karma?21 Questions to Ask a guy 24Have you heard the saying: ‘Do unto others as you would like others to do unto you? Having an existential conversation could unravel interesting thoughts about the meaning of life, love, happiness, and what matters most to you and your love interest.
  12. Do you believe in destiny?21 Questions to ask a guy - destinySome people believe in destiny and some don’t. Either way who doesn’t like to speculate on what the future may bring. Whether it’s the alignments of the stars or universal energies, talking about destiny and what it means to you could be a fun way to get to know someone.
  13. What is your favorite season of the year?21 Questions to ask a guy 27Each season has its own unique attributes, but my favorite season is the fall and all the beautiful arrangement of colors it brings. What is your favorite season? Do you like snowy winters, breezy springs, or maybe sunny summers?
  14. What’s your favorite movie? 21 Questions to ask a guy 27I’m a movie buff. Give me a bucket a warm buttery popcorn and a good chic flick and I’m a happy camper. What are some of your favorite movies and who are your favorite characters?
  15. Do you have a favorite car?21 Questions to ask a guy - carAre you into fast cars or maybe you prefer luxury sedans? Why not get to know someone better by delving into the world of automotive?
  16. If you could be any celebrity, who would you be? 21 Questions to ask a guy - celebrityWe live in a world of reality TV, Netflix, and never-ending celebrity gossip news. What if you were one of those celebrities? Which one would you be? Would you be a famous action film hero, a dramatic vixen, or maybe a rocking music performer?
  17. Would you want to travel back in time? If so, what period would you go to?21 Questions to ask a guy - time travelWhat if you could go back in time? What period of history would you choose? Would you want to travel back to prehistoric times and have a real-life Jurassic Park experience?
  18. What do you see in your future?21 Questions to ask a guy - FutureWhat might the future bring? Maybe this encounter could turn into a world wind romance. Having a fun conversation about where you see yourself in the coming years could lead you to find many commonalities that could bring you and your love interest closer.
  19. Did you have a favorite cartoon as a child?21 Questions to Ask a Guy - CartoonPersonally, I enjoy reminiscing about my favorite cartoon characters. Wouldn’t it be fun to travel back to your childhood and talk about all the cartoons you used to watch as a kid?
  20. Would you rather live in the city or the suburbs? 21 Questions to Ask a Guy - CityMany of my friends are city dwellers and love to be in the hubbub of a busy city café, roam around trendy lounges, or attend late night concerts. I join them from time to time but I definitely like to enjoy the serenity of my suburban neighborhood. What’s your favorite type of neighborhood?
  21. Do you have a pet peeve? If so, what is it?21 Questions to ask a guy - pet peeveI had a friend who would cringe if she heard the sound of someone scraping their nails on a chalkboard. Do you have a pet peeve? Maybe it’s loud chewing or people that drive too slow, or maybe even a word that you don’t like to hear.

Do you have ideas on the best topics to engage into a conversation with someone you just met and would like to know better? If so, we would love to hear from you. Feel free to post your suggestion in the comment section below.

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