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166 Great Personal Questions – Spark deep, meaningful conversations

Why should you know a few great personal questions?

Well… every once in a while, a conversation changes from pleasantries to something a little more personal.

And as long as you have some personal questions to ask, you won’t have anything to worry about!

But what are personal questions?

Basically, they’re questions to ask when you realize you like the person you’re talking to and want to know more about them.

They focus on the subjects of life, death, family, friends, opinions, feelings, and other thoughts many of us don’t like talking about with strangers.


14 Best Personal Questions

The best personal questions are ones that can be asked in any conversation. Luckily we’ve picked out 14 of our best personal questions for you to keep at arm’s reach.

Here are the 14 best personal questions:

1. When you do something positive or helpful to others, do you prefer private recognition or public praise?

Do you want people to know how awesome you are or would a simple “thank you” suffice?

2. What are your guilty pleasures?

I’ve noticed a lot of people are embarrassed about secretly loving when this happens.

3. Upon dying, if you had the choice to re-live your life or live a different life, which would you choose?

Keep in mind, you probably have a much better life than most of the world.

4. Do you have any regrets?

Eventually you have to forgive yourself and let it go.

5. Do you ever feel some people will be better off without you in their life?

In most cases, it’s simply not true because people should be happy to know you!

6. Do you ever feel like you would have been a better person if you never met someone in your life?

That person helped make you the person you are today.

7. Have you ever bullied someone or been bullied yourself?

Kids can be jerks.

8. Do you resent the way you were raised?

Raising a kid is hard and our parents didn’t always get it right. But they love you!

9. Do you hold any grudges against anyone?

It’s normal to hold grudges but eventually the have to be let go.

10. Are you more likely to avoid conflict or engage it head-on?

It’s important to know how to handle confrontation.

11. Do you prefer that people shoot straight with you or temper their words?

Shooting straight is important to being a good communicator.

12. If you could eliminate one weakness or limitation in your life, what would it be?

We all have something we feel holds us back. Perspective always helps.

13. How difficult is it for you to forgive someone who refuses to apologize?

There’s no getting through to some people.

14. Do you hold any convictions that you would be willing to die for?

*Unsheathes knife*

13 Personal Conversation Starters

Conversation starters can be personal too.

Depending on the person you’re talking to and the nature of the discussion, he/she may welcome theses interpersonal conversation starters.

Here are 13 personal conversation starters:

15. You show up to your new job; How do you make friends?

Making friends at work is hard at first but after a while you can weed out your favorites.

16. How have your friends influenced your personality?

The inside jokes and experiences made with friends helped shape you into who you are today.

17. What small things make you happy?

Seeing a stranger smile? Baby animals?

18. Where did you grow up? What was it like?

You can learn a lot about a person from where and how they grew up.

19. What are your siblings like?

No siblings? Parents work too!

20. How’d you meet your best friend?

People love talkinag about how they met their favorite person.

21. If you had a free plane ticket, where would you like to go?

Aruba, Jamaica, oooh I wanna take ya.

22. Aside from the job you have now, what sort of work would you like to do?

What’s your passion?

23. What’s the best part of your daily routine?

Is it a certain caffeinated beverage in your cup?

24. What is something that you know a lot about?

People will talk about their interests for hours if you let them.

25. Why do you think it’s so hard to date these days?

Because it’s not just me, right?

26. What was the most dangerous or most challenging thing that you have ever done?

When did you push it to the limit?

27. Do you have a deep, dark secret?

Coax it out of them.

12 Personal Get to Know You Questions

When you want to get to know someone you have to ask get to know you questions.

And there’s no better way to get to know someone than asking personal get to know you questions!

Here are 12 personal get to know you questions:

28. What do you keep under your bed?

Haven’t you gotten rid of your scab collection from Elementary school?

29. Have you ever won an award?

Something as simple as a 3rd place trophy in the Pinewood Derby or as impressive as the Mark Twain Award.

30. Are you currently happy with your life?

You’d be surprised how many people will answer this if the conversation is good enough.

31. Who is your celebrity crush? Guy and girl.

We all have them.

32. We’re you a good student in school?

What were you like while learning?

33. Which of your possessions could you not live without?

Is your phone really your lifeline in the modern world?

34. What was the last time you cried? Why?

It’s completely healthy to cry. We all experience different moments of grief.

35. What is the one thing that you feel you can never outgrow?

What makes you feel young again?

36. Do you think if you were more well-to-do you’d say goodbye to the friends you have now?

New opportunities breed new relationships. That doesn’t mean you have to cut ties.

37. If you die today, what will you be happy to have experienced?

This question gets you thinking about all the things you still want to do in your life.

38. How often do you fake it?

Sometimes you have to pretend to know what you’re doing even when you don’t.

39. Do you ever feel pressured by your friends to fit in?

Just be yourself and you’ll fit in everywhere.

15 Personal Questions to Ask a Girl

When you’re talking to a girl, whether you like her or not, you should always have a slew of questions to ask a girl.

And you can always pepper your conversation with personal questions to ask a girl.

Here are 15 personal questions to ask a girl:

40. What foundations need to be in place for a relationship to be successful?

A successful relationship requires different things for different people.

41. What are your healthy and unhealthy habits?

Balance is key when it comes to habits.

42. How was your life growing up?

Knowing about her childhood will help you understand her more.

43. Where do you find inspiration?

Inspiration can come from anywhere and when it does, wonderful things can happen.

44. What incident changed your life instantly?

Some of us have experienced life-changing events. It’s healthy to talk about them.

45. Why did you put an end to your last relationship?

If you like her, be sure not to make the same mistakes as the last guy.

46. If I proved to you that you were dreaming right now, would you want to wake up?

This is one way to tell if a date is going south. It’s also fun to ask.

47. What is the dumbest thing you have ever believed?

I used to believe in Bigfoot but if he were real, wouldn’t we have found him by now?

48. How do you want to retire?

Retirement can get boring. How would you keep your Golden Years interesting?

49. How do you manage your work and personal life?

Are they separate or often intertwined?

50. What is the perfect partner?

What can you work towards?

51. What are your deal breakers?

These often arise from past failed relationships.

52. Do you want kids?

If a relationship is going to last, you’d better be in agreement here.

53. What are the most annoying things that men do in a relationship?

We try not to be annoying but it’s hard sometimes.

54. What have you always wanted to try?

Add it to the date list.

13 Personal Questions to Ask a Guy

Your girlfriend’s friend or a potential business partner often become conversation partners and when that happens you should have some questions to ask a guy handy.

Even if you want to make a new friend, personal questions to ask a guy often come in handy.

Here are 13 personal questions to ask a guy:

55. Have you ever cheated on someone or helped someone else cheat?

Either way, it shouldn’t feel good afterwards.

56. What are some buy-it-for-life items you own?

A belt with a lifetime guarantee? A backpack made to last? Sometimes it’s worth it to spend a little extra.

57. What do you view as a waste of money?

What can’t you justify spending money on?

58. Should the man always pay for dinner?

I like switching off. You both bring something to relationship and you get to surprise each other from time to time.

59. How do you stay healthy? What’s your workout routine and diet?

The best workout is the one you do every day.

60. What actions define a man?

It’s what you should constantly strive for.

61. Would you rather get married or is it too much of a hassle?

Divorce can be expensive and being legally married isn’t always ideal for everyone.

62. If you get to name your kids, what would you name them?

Kanye was in charge of naming his kids. Will you be as creative?

63. Is it okay to lie in a relationship?

Sometimes the truth hurts. Does that make it okay to lie?

64. How do you stay organized?

You might learn a new tactic to help your organization.

65. What instantly makes you angry?

Some things just set us off.

66. What was the best date you’ve ever been on?

You might learn a thing or two by asking this as well.

67. What public phenomenon do you find awkward?

For me, it’s when people clap along to live music. Keeping a beat is surprisingly hard for some people.

11 Personal Questions to Ask Friends

Maybe you want to become even closer to a friend of yours.

Our list of questions to ask friends is a great resource, but here are some personal questions to ask your friends for a more intimate encounter.

Here are 11 personal questions to ask friends:

68. How do you behave around colleagues?

Some people tone it down at work.

69. How much do you want to achieve in your life?

Maybe you can help. That’s what friends are for after all.

70. Have you ever experienced something you couldn’t explain?

A missing hoodie or a ghostly apparition?

71. What would you do with $1,000,000?

I’ll gladly help you spend it.

72. Do you ever feel held back by your status or background in life?

What happened in the past is in the past. You make your future.

73. Do you stay in touch with people forever or maintain distance when they are not part of our life anymore?

Dunbar’s number is an interesting theory to look into.

74. What do you think about your first impression on people?

How do you want people to see you?

75. What is the best thing about your best friend?

You love your best friend and you should express it!

76. When does an acquaintance become a friend?

At what point does a buddy become someone you can count on?

77. When you’re upset, do you want space or attention?

Some people need to process their feelings before acting while others like to let it all out as soon as possible.

78. What is the first thing you do when you wake up?

How do you start your day off right?

14 Personal First Date Questions

One of the most important times to have prepared questions is on a first date.

Start off with general first date questions and move into more personal territory with the following questions.

Here are 14 personal first date questions:

79. What is your favorite little-known place in your city?

It’s important to be a tourist in your own town from time to time. You’ll become an ambassador of sorts and find some hidden gems.

80. Where do you want home to be when it’s time to settle down?

Some people never settle and that’s okay too.

81. What roles should each party have in a romantic relationship?

A relationship takes a little bit from both parties. How do you keep one together?

82. What was the best birthday of our life and why?

We threw a surprise party for my friend once. We printed out a bunch of pictures of his face and everyone sat in the dark with them strapped to their faces until he got home. He was rather surprised.

83. How do you relax when frustrated?

It’s important to maintain your composure when the going gets tough.

84. How can I instantly put a smile on your face?

Make people smile, make the world a brighter place.

85. What are the three most important things in your life?

What do you cherish every single day?

86. What’s your favorite vacation spot?

Travel is important to becoming a more grounded individual. Doing it solo is even better than in a group too.

87. What was your first impression of me?

Bad first impressions can be mistaken but it’s best to avoid them in the first place.

88. Who inspires you the most?

Having someone to look up to inspires us to be better and work harder.

89. Which company would you want to work for at least once in your lifetime?

A fancy Silicon Valley startup? An fishing boat off the coast of Bora Bora?

90. What was your most successful relationship? Why was it so successful?

It’s something to work towards.

91. If you were appointed Leader of the world for the day, what changes would you make?

How would you create a utopia in a day?

92. What are your favorite flowers?

You now have something to bring to the second date if all goes well.

16 Personal and Funny Questions to Ask

Everyone loves to laugh so be sure to always have a few funny questions to ask.

Of course, funny questions can be personal too!

Here are 16 personal and funny questions to ask:

93. What’s the worst thing a person can do that isn’t illegal?

How can you leave the most emotional scars on someone?

94. When was the last time you screamed at the top of your lungs?

Why not do it right now? The looks you’ll get will make for a great memory.

95. What is the worst thing that somebody has walked in on you doing?

It happens and it’s always awkward for everyone involved.

96. What is the weirdest nickname people call you?

My friends call me Kaaaaarrrrl because of that Llama that goes mad in those YouTube videos.

97. What’s the most personal question you have ever answered?

A question about a question? Hah, that’s funny!

98. How difficult is it for you to be honest, even when your words may be hurtful or unpopular?

Honesty is the best policy but it’s not always easy to maintain.

99. In what area of your life are you immature?

Where do you struggle at being a functioning adult? All it takes is a little discipline.

100. Are you always this high maintenance? Explain.

A fun way to surprise someone.

101. What is one guilty pleasure you enjoy too much to give up?

Balance is key for everything in life. We have to indulge our wild side from time to time.

102. When making an entrance in to a party, do you make your presence known?

Do you need one of these every time you walk into a room?

103. How often do you doodle? What do your doodles look like?

Here’s to all of the margins I’ve drawn random spirals and cool S’s on.

104. When do you find yourself singing?

Belt it out. It’s cleansing.

105. Why do they say flattery won’t get you anywhere?

Many people can tell when you’re sucking up. Does flattery sometimes work?

106. Why shouldn’t we take life seriously?

Does any of this even matter enough to take seriously?

107. How do you make something idiot proof?

Where there’s a will, there’s a way for someone to screw it up.

108. Who performs the most random acts of kindness out of everyone you know?

We need more people like that in the world.

18 Personal and Deep Questions to Ask

For centuries, deep questions to ask have been pondered by man.

So the next time you’re spending time with people on a warm summer evening, become a critical thinker and try out these deep personal questions to ask.

Here are 18 personal and deep questions to ask:

109. What is something about life that people don’t appreciate as much as they should?

A beautiful sunset? The night sky? Youth?

110. Do people have a right to be happy or should they have to earn it?

On a social scale? A political scale? A cosmic scale? Where does happiness come from?

111. What is a year of life worth? How about a day?

What metric do you use to define the worth of time?

112. What is the purpose of a human life?

Is there one?

113. If you died today, how would you be remembered?

If you don’t like what you see, it’s time to make some changes!

114. How would you react if there was irrefutable proof that God doesn’t exist? How about if there was irrefutable proof that God does exist?

Would you be able to accept it?

115. Where is your life headed?

Ask yourself this from time to time. It will keep you grounded.

116. What is holding you back from being the person you want to be?

Maybe it isn’t holding you back as much as you think.

117. How would you describe yourself in three sentences?

These sentences can be your mission statement. Something that describes exactly what you’re all about.

118. Do you follow politics?

If you both do, a conversation might erupt! If not, you can both happily avoid the subject.

119. What event would you rather die than live through?

Definitely not Pompeii.

120 Why do some people stay in relationships that they know are toxic?

Because the unknown is terrifying.

121. Who should be responsible for taking care of the elderly: The government, their families, or the elderly themselves?

If you were elderly, which would you prefer?

122. What do you consider a wasted life?

Why is it so hard for some people to have a happy and healthy life?

123. What would the perfect You be like?

This one really pulls at your insecurities.

124. What is the most worthwhile goal a person can dedicate their life to?

What can a person do to make the world a better place?

125. Why do people do things that they know hurts themselves and those around them?

Habit? Lack of empathy? Personal battles?

126. What stops people from understanding themselves?

We have to spend our entire lives with ourselves and some of us never learn who we truly are.

10 Interesting Personal Questions

If you’re going to get personal with someone, you can’t just ask the same boring questions they’ve heard a million times. Instead, ask interesting questions that allow them to show their most interesting—and personal—side.

Here are 10 interesting personal questions:

127. Do you think someone is better than you at your job?

This question shows how much awareness, humility, and honesty the answerer has.

128. Is it easy for you to show yourself love or speak kindly to yourself?

An interesting question that people are never asked, for some reason.

129. What do you want people to feel when they’re around you?

A roundabout way of asking a very important question: who do you think people think you are?

130. Do you think your parents did a great job raising you?

Parents, childhood, and an evaluation of themselves in the present: all interesting topics in this one question.

131. Do you believe in Karma as “what goes around comes around”?

The answer always impacts how someone sees the world.

132. What was the experience that impacted you the most in your life?

Choosing just one really makes people share something about themselves.

133. Do you usually follow your heart or your head?

Don’t let them pretend they don’t give one preference in each choice.

134. What do you prefer stability or spontaneity?

No wrong answers, but everyone prefers one or the other.

135. What is the best advice you’ve ever been given?

A chance to learn something personal and interesting, as well as gain some real wisdom.

136. Excluding romantic love, have you ever told someone you loved them?

It’s a word we use to rarely with friends. Change that with this question.

9 Would You Rather Personal Questions

Sometimes, the best way to get personal is indirectly, through fun, silly games. You can use would you rather questions to get beyond surface-level chat and really dig into the personal stuff.

Here are 9 would you rather personal questions:

137. Would you rather die young or live until you’re old?

Answers usually depend on how old the person is.

138. Would you rather end hunger or hatred?

This leads to some very deep, philosophical conversations about the nature and sources of hunger and hatred.

139. Would you rather have many good friends or one very best friend?

Is it the number or the quality that counts?

140. Would you rather be happy or be rich?

Is it possible to be both?

141. Would you rather be without eyes or a mouth?

Imagining life without either is a trip.

142. Would you rather go into the past and meet your ancestors or go into the future and meet your great-great-grandchildren?

It’s all about how we orient our lives towards the past or the future.

143. Would you rather find out that there’s God just like the Bible says or find out there’s no God out there?

A theological question we’ve all asked ourselves—alone—at some point. Share your answers now.

144. Would you rather be poor and work at a job you love, or rich and work at a job you hate?

Also known as “millennial’s choice.”

145. Would you rather they find the real cause of your death or miss it and make you a famous case

A great question to consider our cultural obsession with fame.

9 Weird Personal Questions

Getting personal is uncomfortable for most people, but you can make that easier by digging in with these weird questions to ask. When you go weird, people feel a little more comfortable opening up, because the conversation is already a bit bonkers.

Here are 9 weird personal questions:

146. Do you pluck or shave or wax your underarms?

A grooming tip that often comes with a laugh.

147. Was there ever a time you literally thought out loud?

Have them act it out to make it extra fun and extra personal.

148. Do you pray before sleeping?

This is a weird—but effective—indirect way to get into a conversation about God.

149. How do you deal with a stressful situation?

How we cope with stress tends to be very personal and very telling.

150. How many hours of sleep do you usually get?

We could all use more, but how much are they missing out on? And why?

151. Do you think astrology is crazy or accurate?

Astrology always brings up a lot of passionate debate. Which side are they on?

152. What keeps you up at night?

You’re really asking what it is that truly worries them about life and the world.

153. How do you approach a person who is known for his difficult attitude?

This is telling about their personality…and also a great way to pick up tips for your next encounter with Mr. Difficult.

154. What’s the most surprising self-realization you’ve had?

Hit them with this after a few other weird ones, to really get personal.

personal questions to ask a new friend

Even if you’ve just met your friend, you shouldn’t be afraid to ask some personal questions as long as they’re willing to answer. If you’re looking for the right not too intrusive personal questions to ask a new friend then you’re in the right place.

Here are 7 personal questions to ask a new friend:

155. Do you have any fears?

Don’t take it personally if they don’t want to answer.

156. What do you like most about your family?

The things we like most about our family can manifest themselves in how we are as people.

157. Who was your role model growing up?

It’s interesting to know who helped them be the way they are.

158. What keeps you up at night?

It’s the thoughts that keep us up at night which means the most to us.

159. What do you think is the worst way to die?

It’s something that’s slow and painful, probably.

160. What is your love language?

It’s important to know someone’s love language even if you’re just starting out as friends.

161. What habit are you trying to quit?

Maybe you can help give them that extra push.

5 personal questions to ask your crush

You want your relationship with your crush to be as deep as possible. You want to know more about them. That’s why you should know the right questions to ask your crush. Those that will lead you to a deeper level of understanding with them.

Here are 5 personal questions to ask your crush:

162. What’s your greatest fear?

When you think of personal questions, this one is the most common. You can dig deep about her with this one.

163. What’s something you find attractive that most people don’t?

The weirder the answer, the better. Sometimes, we don’t need to cave in to society’s standards. You’ll know more about what she likes and what attracts her. Take notes!

164. If you have a free day, how do you usually spend it?

It’s refreshing to have a free day when you don’t have to succumb to your daily routine. You’ll know more about her from her answer to this question.

165. What’s the one thing that drives you crazy about other people?

Some people just have that habit or thing about them that can drive you nuts. And you don’t even know why!

166. If you could have one superpower for a day, what would it be?

The list of superpowers is endless. The more creative answer she can come up with, the more fun.

Downloadable and Printable List of Personal Questions

Here is a downloadable and printable list of personal questions (right click the image and select Save Image As…):

List of Personal Questions

More Great Questions To Ask

When personal questions become tedious, you can always mix things up. Try some of these great questions to ask for a successful conversation with anyone.

  1. Ever run out of things to talk about? That won’t happen anymore if you have some conversation topics on hand.
  2. Fun questions to ask are great for having a… well… fun conversation.
  3. You can always learn something new about your romantic partner. Our questions for couples will keep things romantic, fiery, and interesting.

How to Ask Personal Questions

Are there rules for asking personal questions? Societal norms say yes! So be sure to keep these steps in mind when asking personal questions.

Here is how to ask personal questions:

1. Don’t start with personal questions

Getting too personal too quickly can drive some people away so it’s best to ease into these questions while you’re on the subject.

2. Share your own experiences

If you’re only asking questions and not providing details about yourself, you’re not in a conversation; you’re in an interview.

3. Respect Boundaries

Recognize when the person you’re talking to is uncomfortable by the questions you’re asking and back off when necessary. If you can’t tell, just ask!

In Conclusion

When you want to turn an acquaintance into a potential friend, or when you simply want to know more about the person you’re talking to, personal questions are some of the best questions to ask.

So get out there and get personal.

About The Author


Jasper is our expert conversationalist and wordsmith. He loves coming up with questions, jokes, and topics designed to create natural conversation. His work has been featured on, iHeart Media, Elite Daily, and The Urban List. Jasper lives in Georgia with his new bride.

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