Questions to Ask a Guy

Sometimes it can be challenging getting a guy to open up and talk about things. It is one of the biggest complaints women have about their boyfriends, husbands, and sons. In many cases, guys are willing to share information, but they do not know where to begin the conversation. They might be willing to discuss things if their significant other or parent presents a question in the right way.

The key to getting a guy to open up is to approach him in a non-threatening manner. A woman who is frustrated might be tempted to say phrases like “You never tell me anything!” or “Why won’t you talk to me?!” This makes a guy feel defensive and he is less likely to share if he feels threatened or attacked. Instead of approaching a conversation from a negative point of view, think of a few questions you want to ask the guy before you proceed. Make sure questions show interest in his likes and dislikes, and make sure the questions are not overly personal. If you are just getting to know a guy, you can modify some of the more intimate questions to make them more appropriate. Here are several questions to ask a guy when you want to get him talking and sharing information with you:

Twenty Questions to Ask a Guy

Questions about your relationship

  • What can I do to make our relationship better?
  • What habit of mine would you change if you could?
  • What is your favorite memory we have shared?
  • What is one thing you would like to do together in the coming months/years?
  • What were you most surprised to learn about me?

Questions about his ambitions and goals

  • What have you done that makes you most proud?
  •  What do you want to accomplish in the next five years?
  • What is your dream career?
  • What do you consider your biggest success?
  • What is one mistake you regret?

Questions about his family

  • Who is your favorite relative?
  • Did you have a happy childhood?
  • Would you prefer to be an only child, have a few siblings, or have many siblings?
  • Would you want a marriage like your parents?
  • What was your best family holiday and why?

Questions about his views on the world

  • What is your biggest pet peeve?
  • Do you think society is headed in the right direction?
  • What would you change about today’s world?
  • If you could live during another period in history, what would you choose?
  • Do you think having children is a good idea nowadays? Why or why not?

These 20 questions to ask a guy can spark detailed conversations and help you get to known a man better. It does not matter if you have just started a friendship or romantic relationship, or you have been together for years, the questions on the list help you learn more about the man in your life and show him you are truly interested in getting to know him better.

Random Questions to Ask a Guy

If the 20 questions to ask a guy listed above are too intimate for your relationship at the moment, you might want to start with light-hearted, basic questions. If you are in the early stages of your relationship or you are dealing with a guy who is shy and reserved, consider a few of these random questions to ask a guy:

  • What is your favorite food?
  • What is your favorite restaurant?
  • What type of music do you currently enjoy listening to?
  • What’s the most fun thing you have done in the last few weeks?
  • Are you looking forward to any upcoming plans?
  • Have you visited the zoo/museum/local attraction recently?
  • Have you been getting along with your friend recently?
  • Are you learning anything new in school or taking on any new projects at work?
  • Have you met anyone interesting lately?
  • Have you shopped for new clothes or other new items recently?
  • What is the strangest thing you have seen in the past few months?
  • When was the last time you played your favorite board game?
  • Have you recently had time to enjoy your favorite hobbies?
  • What would you like to make time to do in the coming weeks?
  • Have you exercised recently? What fitness activities do you enjoy?
  • When was the last time you laughed really hard?
  • What is your favorite television show at the moment?
  • When was the last time you had a home cooked meal?
  • Have you enjoyed the weather recently? What is your favorite season?

These questions are geared toward a man you do not know that well, but with a few adjustments, you can ask any man in your life similar questions. Many of the questions also focus on recent events, so even if you know a man’s favorite food, you might not know he had the best sandwich of his life the other day for lunch. You might know what his hobbies are, but you might not know what he has recently done to enjoy his hobbies.

These questions can lead to deeper conversations, but they can also be pleasant even if they go no further than a basic answer. They are great to ask when trying to catch up on the news in a man’s life or when trying to get a guy to open up and share information. Showing interest in his life, no matter how deep questions go, make a guy feel special and interesting. If you are looking for a way to spark conversation with a man in your life, these questions to ask a guy should do the trick.