Fun Questions to Ask Anyone

The art of conversation is more about what you get others to say than what you contribute to the conversation.  People love to talk about themselves, and if you have some fun questions to ask in different situations, you’ll be the person known for keeping interesting conversations going in any situation.

If you’re sometimes uncomfortable in certain situations (one a date or when you’re at a party, for instance), a few interesting questions can become real ice breakers.  You’ll soon be involved in an interesting conversation and you’ll learn a lot about the people you’re talking to.

A Few Fun Questions to Ask on a Date

Those first few dates can be awkward, but if you ask the right questions, you’ll get them talking honestly about themselves.  You can learn a lot about their personality and their likes and dislikes by asking some challenging but fun questions.

“What do you do in your spare time?” is a great way to get the ball rolling.  You’ll learn whether they are active or more laid-back and what types of activities are favorites.  You may even discover shared hobbies you can do together.

“What one thing are you most proud of?” is very revealing.  It will tell you what the person values most – personal achievement, their appearance, money, etc.

“Tell me about your family,” isn’t really a question, but it’s a good way to learn how the other person feels about family ties and how he handles his relationships with those closest to him.  If you’re a family oriented person and your date says, “I’m not really close to my family,” you’ve learned about a potential conflict.

Fun Questions to Ask Your Boyfriend


Questions for your boyfriend should focus on opening him up and learning more about how he feels regarding your relationship.  It’s best to ask these questions when he’s relaxed and won’t feel threatened.  Some of the best questions to ask your boyfriend include:

  • “Where do you think we’ll be in five years?”
  • “Would you like to take a vacation together, and where?”
  • “What, if anything, would make you leave your career?”
  • “If we only saw each other once a week, what would you want to do?”

Fun Questions to Ask Your Girlfriend

Guys can learn a lot about their girlfriend by asking the same questions.  There are also fun questions for girlfriends that are unique to women, but in general you can interchange the questions to learn more about your significant other.

  • “If you had children, do you think it would be hard to juggle your career and being a mother?”
  • “What are you most looking forward to in the next year?”
  • “What is the most important thing you’re saving up for?”

Fun Questions to Ask Friends

Asking fun questions can really open up new understanding between friends, and the right ones can be either hilarious or inspiring.  Fun questions to ask friends can also be revealing; you may discover a lot of things you never knew about your closest friends.  When you ask, be willing to give your answers as well.

  • “Who do you think is the sexiest man/woman alive?”
  • “How old do you think you’ll be when you have kids?”
  • “If you had unlimited money for one week, how would you spend it?”
  • “What would you do for a million dollars?”
  • “Have you ever rescued someone?  What were the circumstances?”

Fun Questions to Ask Your Spouse

Even after being married for years, an evening of asking each other questions can lead to personal discoveries that will enrich your relationship.  There are lots of fun questions to ask your wife or husband that can lead to a closer relationship.

  • “When did you first fall in love with me?”
  • “How do I make you feel loved?”
  • “What is your favorite time of day when we are together?”
  • “What one thing would you change about your past?”

Fun Questions to Ask Your Wife

Some questions are geared more toward women than men in a marriage and vice versa.  Men can learn a lot about their wives by asking the right questions.

  • “How do you feel being the primary caregiver for our children?”
  • “Do you ever feel like you need some time to yourself?”
  • “What one thing do I do that makes you feel special?”

Fun Questions to Ask Your Husband

There are also questions that can help wives understand their husbands more:

  • “Do you ever feel like your career is overwhelming?”
  • “Do you hide some things from me to save me from worry?”
  • “Do you ever wish you could trade places with me?”

Fun Questions to Ask Kids

Kids answer questions with amazing honesty.  They will usually give you detailed, elaborate answers and are uninhibited in their responses.  A few fun questions answered by kids you’re close to can really brighten your day.  There are standard questions that have stood the test of time, such as, “What do you want to be when you grow up?” as well as lots of others:

  • “If you could be an animal, what animal would you want to be?  Why?”
  • “What would you buy with $100?”
  • “Who is your hero?”
  • “What one thing would you change about your school?”
  • “What is the most beautiful place you’ve ever seen?”

Fun Questions to Ask People in General

Sometimes you are in a group of people at a party where you don’t know anyone, or you may be sitting with someone waiting for a bus.  There are plenty of situations where you may strike up a conversation to pass the time, but aren’t sure what to talk about.  Below are a few great questions that will add interest to any conversation, whether you are on intimate terms or you’re talking to virtual strangers.

  • “What is the ultimate dream vacation?”
  • “Who influenced you most when you were a child?”
  • “Who influences you the most now?”
  • “What is the most daring or dangerous thing you’ve ever done?”
  • “What person in history would you most like to meet?”

There are also fun questions to ask someone when you want to know how they feel about a particular issue, such as politics.

  • “What one thing would you change about our government?”
  • “Why do you belong to the Democratic/Republican/Other party?”
  • “Who do you think would make a great president?”
  • “If you could run for public office, would you? Why or why not?”

Fun Questions to Ask Guys or Gals

Consider an evening of asking each other questions if you have friends who are both guys and gals.  Asking gender specific questions can really be surprising.  Girls may learn a lot about how guys think, and the guys may discover some surprising truths about women.

Fun questions to ask guys might include:

  • “What is the sexiest part of a woman?”
  • “Do you like to open doors, etc. for a woman?”
  • “What one thing about women mystifies you the most?”
  • “What would you do if you were a woman for a week?”

Fun questions for gals might be:

  • “What is the sexiest part of a man?”
  • “Do you think there is a double standard for men and women?”
  • “What one thing confuses you most about men?”
  • “What would you do if you were a man for a week?”

The possibilities to learn more about others is almost limitless if you ask the right questions.  Try to ask questions that can’t be answered with a simple yes or no.  Open ended questions that require some thought are the best way to learn more about how others think and react.  With some practice, you’ll come up with your own fun questions to ask others, and you’ll learn a lot about your friends and family along the way.