65+ Really Fun Questions to Ask That Will Lead to Some Amazing Answers

Here are some really fun questions to ask and answer. They cover all kinds of different subjects, so there are sure to be some that’ll be perfect for you and the person you’re talking to.

We’ve got some more links to other fun questions to ask at the bottom of the page, so don’t forget to check those out as well.

Fun Questions to Ask

A lot of these questions will bring out some really funny answers, and some are just enjoyable to discuss. There are also some that might lead to an interesting deeper discussion but those are few and far between. We also have a great collection of Topics To Talk AboutQuestions to Ask a Girl.

10 Fun Conversation Starting Questions To Ask

There’s nothing more awkward than meeting someone new and panicking to find something to talk about.

Small talk will last you a minute or two, but what you need in that moment are conversation starters that will lead you towards an fun, fascinating conversation. Before you know it you and your new friend will feel at ease and open, and the conversation will flow naturally.

Here are 10 fun conversation starting questions to ask:

1. On A Scale Of 1-10, How Strict Were Your Parents?

On either end of the scale, parents are a great source of stories.

2. Who Was Your Worst Teacher? Why?

Bad teachers are the stuff of nightmares.

3. Who Was Your Favorite Teacher? Why?

Great teachers can change a student’s life forever.

4. What Was Your Favorite Toy Growing Up?

Childhood toys keep their sentimental value for life.

5. If You Could Time Travel, When Would You Go?

First stop: wherever Mary McFly got his Nike’s.

6. What’s Your Best Childhood Memory?

Tapping into childhood memories is a great conversation starter.

7. What’s Your Pet Peeve?

People can be annoying, but venting helps.

8. What Personality Trait Has Gotten You In The Most Trouble?

Everyone has a natural tendency that has caused them trouble in the past.

9. What Is The Best Piece Of Advice You’ve Received?

Good advice works best when it’s shared.

10. If You Had To Pick A New Name For Yourself, What Name Would You Pick?

Some names seem to fit certain personalities.

10 Best Fun Questions To Ask

The best fun questions to ask all have a few things in common: they focus on positive ideas and memories, they are great segues for fun stories, and they show your interest in the person you’re speaking to.

Use these questions next time you’re with someone riding in the car, sitting down to lunch, or grabbing drinks.

Here are 10 of the best fun questions to ask:

11. What Accomplishment Are You Most Proud Of?

Everyone loves a chance to brag a little bit.

12. Which Of Your Friends Are You Proudest Of? Why?

A person who can recognize greatness in others is the type of person you want to keep around.

13. What’s The Most Beautiful Place You’ve Ever Been?

This is a great way to begin a conversation about travel.

14. Do You Feel Like A Leader Or A Follower?

All societies needs both types.

15. What’s The Most Courageous Thing You’ve Ever Done?

Moments of true courage are rare and inspiring.

16. When You’re Having A Bad Day, What Do You Do To Make Yourself Feel Better?

Everyone needs a feel-good ritual.

17. Which Would Be Harder For You To Give Up: Coffee Or Alcohol?

Which method of self-medicating is most important?

18. What Is Your Favorite Wikipedia Article?

No matter what your teachers said, Wikipedia is the ultimate collection of mankind’s knowledge.

19. What’s Your Favorite Cheesy Pick-Up Line?

It might be time to try out that old favorite again.

20. Can I Get You Another Drink?

Everyone’s favorite question.

5 Fun Would You Rather Questions

Would you rather questions are like the multiple choice section of a test. You still have to think about your answer, but you have options to choose from.

The best thing about these questions is that there’s no wrong answer, and the questions are all fun.

Here are 5 fun would you rather questions:

21. Would You Rather Burp Every Time You Lean In For A Kiss Or Drool Every Time You Talk?

Either way, good luck in the dating scene.

22. Would You Rather Not Brush Your Hair Ever Or Your Teeth?

Some of us already make this choice when we’re running late.

23. Would You Rather Sleep Wearing Handcuffs Or A Bike Helmet?

I guess the answer depends on what else happens in bed.

24. Would You Rather Embarrass Yourself At A Party Or Get Caught Making Out With Your Best Friend’s Sister?

Either one will seriously impact your social life.

25. Would You Rather Be Uncontrollably Laughing For The Rest Of Your Life Or Uncontrollably Crying?

Laughter requires less clean up but can land you in hot water in the wrong setting.

7 Incredibly Funny Questions To Ask

There’s something about funny people. They’re magnetic. They lift the moods of everyone around them. They make great first impressions.

Whether you’re a naturally funny person or someone who’s comedic skills could use a little work, this list of funny questions to ask will draw smiles and laughter from your conversational partners and endear you to them from the very first encounter.

Here are 7 incredibly funny questions to ask:

26. If You Could Ask Your Pet 3 Questions, What Would They Be?

You always ask who’s a good boy, but what about how’s a good boy?

27. What Is The Funniest Thing You Have Ever Seen A Stranger Do?

People watching is the new national pastime.

28. Do You Think Cats Have Any Regrets?

Do those jerks have any remorse?

29. How Many Days Do You Wear The Same Pants In A Row Before It Becomes A Problem?

Pants: the napkin you wear.

30. What Are Your Movie Theater Popcorn Habits?

How many previews before you need a refill?

31. Which Room In Hogwarts Would You Most Want To Have Sex In?

What happens in the Chamber of Secrets stays in the Chamber of Secrets.

32. Do You Put The Toilet Paper Roll On The Right Way Or The Murderer Way?

Yes, there is a right way.

There is a time for deep questions, there is a time for serious discussions, but there is also a time for fun.

This list of fun questions to ask a girl is designed to keep things your interactions with the ladies light and interesting.

They’re the type of questions that are answered with a laugh and that light touch on the arm that lets you know things are going well. Pick your favorites from this list before a night on the town or a date with your lady and be prepared for sparks to fly.

Here are 10 fun questions to ask a girl:

33. What Would Your Perfect Saturday Be Like?

Take notes and plan accordingly.

34. Which Movie Sequel Do You Wish You Could Erase From History?

Sequels are notoriously disappointing.

35. What Would Your Perfect Vacation Entail?

Mountains, beaches, or exotic lands?

36. What’s A Great Book You’ve Read Recently?

Literary tastes are a good signal of personality traits.

37. What’s The One Food You Could Never Bring Yourself To Eat?

Remember the show Fear Factor?

38. What’s Your Dream Job?

Imagine money wasn’t an issue, what would she want to be doing?

39. Cake Or Pie?


40. Who Is The Kindest Person You Know?

Just thinking about the person is likely to put a smile on her face.

41. What Fictional Character Do You Wish You Could Meet?

It’s amazing how much a made up person can impact real life.

42. What’s The First Thing You Do When You Get Home From A Trip?

After kicking off her shoes, of course.

10 Fun Questions To Ask A Guy

Men’s minds work differently than women’s. We can argue whether or not that’s a good thing, but the truth is that we tend to think about different things in different ways.

The following list of fun questions to ask a guy is designed hit the topics that men think and talk about, and is sure to come in handy whether you’re meeting someone new or hanging out with the crew.

Here are 10 fun questions to ask a guy:

43. What Was The Funniest Way That You Have Been Injured?

Goofy injuries are just part of being a man.

44. If Your Life Was A Movie, What Songs Would Be On The Soundtrack?

This question will tell you about his musical tastes and personality.

45. What TV Catch Phrase Do You Most Enjoy Using?

Catch phrases may be a thing of sitcoms past, but they’re still hilarious.

46. What Terrible Movie Do You Love?

There’s a certain pleasure to be found in awful movies.

47. What Song Do You Have To Sing Along With When You Hear It?

Get the answer and find a karaoke bar, stat!

48. What Game Are You Really Good At?

Drinking games, card games, board games… everyone excels somewhere.

49. Which Movie Do They Need To Make A Sequel To?

So many great movies have left us wanting more, what would he like to see?

50. What’s The Right Age To Get Married?

It’s amazing how much the answer will change from person to person.

51. What’s Your Favorite Childhood Book?

Berenstain Bears conspiracy aside, those books were great.

52. If You Could Choose Your Own Nickname, What Would It Be?

People usually have no say in their nicknames, give him the power to choose his own.

7 Fun Questions To Ask To Get To Know Someone

Getting to know someone, to really know them, can be a challenge.

It’s a process that requires time and dedication, but as you know from the close relationships you already have,

Getting to know people is worth the effort.

These get to know you questions are a fun, easy way to set off on the path towards friendship. Just because it takes some effort, doesn’t mean it can’t be fun.

Here are 7 fun questions to ask to get to know someone:

53. What Are Your 3 Favorite Movies?

Shared taste in movies is a surprisingly good basis for a friendship.

54. If You Had To Live In A Different State, What Would It Be?

Every state has something to offer, it just depends on what you’re looking for.

55. As A Child, What Did You Wish To Become When You Grew Up?

So few people actually become what they wanted to be, but it’s fun to reminisce.

56. What Extracurricular Activities Were You Involved In During High School?

This question will give a quick peek into what someone was like in the most awkward time of life.

57. Are You Spiritual Or Religious In Any Way? If So, How?

Spirituality can be central to a person’s identity.

58. Do You Think Of Yourself As Being Naughty Or Nice?

The price of fossil fuels is going down, but some people embrace the naughty lifestyle anyways.

59. Are You Old-Fashioned?

This question is pretty broad, let them interpret however they choose.

9 Fun, Random Questions To Ask

This list of fun random questions to ask hits on all kinds of topics.

No matter the context of your conversation, you’ll find a question here to keep things flowing in a fun, positive direction.

Here are 9 fun, random questions to ask:

60. If You Could Have Dinner With Anyone From History, Who Would It Be?

History is full of people who would make great dinner dates.

61. Who Would Play You In A Movie Of Your Life?

Be sure to ask if that casting decision is based on appearance or personality.

62. If You Could Shop For Free At One Store, Which One Would You Choose?

Whether the person chooses pragmatically or

63. What’s The Worst Thing You Did As A Kid?

We do terrible things before we know better, and those things make great stories.

64. If You Could Marry A Fictional Character, Who Would It Be And Why?

Everyone has fallen for someone who doesn’t actually exist.

65. What Television Show Do You Plan Your Day Around In Order To See It Live?

We live in the golden age of TV

66. Which Is Better—A Novel Or A Movie?

Both mediums offer something that the other can’t.

67. If You Could Read Minds, Whose Would You Want To Read?

The girl at the coffee shop? The boss at work? So much snooping to do!

68. If You Were Told You Only Had One Week Left To Live, What Would You Do?

What dreams would he or she fulfill with that ultimate motivating factor?

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Written by Naveen

Entrepreneur | Web Developer | SEO Analyst | Animator


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