Skip to Content
ebay rolex replica watches luxury replica mens watches blancpain watches replica us replica watch 32 rolex replica trusted watch replica sites diferencia entre rolex original y replica hublot all black replica men's rolex presidential replica watch faux rolex watches

A Collection Of Getting To Know You Questions For A Deeper Insight

A Collection Of Getting To Know You Questions For A Deeper Insight

If you’re looking for the perfect icebreaker and some effective conversation starters, you’ll be pleased to know you’re in the right place.

Getting to know someone has never been this fun!

Instead of coming up with the questions yourself, I’m here to help you get to know that person you’ve been dying to get to know so much better.

cute and young couple talking on the couch

This could be a casual friend who you’ve just started hanging out with and you want to deepen your bond.

It could be a new potential relationship that you’re trying to spice up by asking some fun questions but also personal questions that will help you forge a stronger bond.

It could even be a family member who you’ve never really asked those deep questions that you’ve always wondered about.

Here, you’ll find the best questions for any person and any situation that will be the perfect icebreaker questions and awesome conversation topics for when you run out of things to talk about.

friends sitting on a wall and talking by the water

I’ll cover everything from family stuff, small talk, career, co-workers, relationships, bucket list items, and irrational fears!

All in all, there will be some truly great questions that will help you penetrate even the most introverted person’s mind and get you to talk!

First, I’ll start with some fun questions on a less invasive level to break the ice and help you ease into those deeper questions.

Then, we’ll switch gears and get a little more personal with some deep questions but still not completely over-the-top.

And finally, we’ll get to those big, intriguing, most personal questions one could ask that should be reserved only for those you’ve already forged close bonds with, so there are no awkward moments.

young cute couple talking while laying in bed

It’s important that it feels natural and safe and you’re the best judge of who you can achieve that with.

Without further ado, let’s start asking those tough questions and uncover some deeply rooted secrets you’ve been yearning to find out (I’m just kidding of course, but hey, who knows what might end up happening!)

Here we go! We’ll start slow and see where the curiosity takes us.

See also: 20 Legit Signs You’re Still A Kid At Heart

Casual Get To Know You Questions

2 friends sitting on a bench in the street and having a conversation

These get to know you questions are the perfect icebreakers for when you’re just getting to know a person and you wish to take it to another level.

You could be on your second date with a person you feel really comfortable with and you want to spice it up with some fun questions or it could be with a new friend.

You get the point, so let’s see what we’ve got for you.

1. What was your favorite subject in school and how did you do on it?

2. What’s your biggest pet peeve about people and how long has it been bugging you?

3. When was the last time you did something really crazy out there and spontaneous and would you do it again?

4. Would you slap your best friend if you were offered a thousand bucks for it?

5. What’s the one TV show you think is severely overrated but you know you’d get a lot of crap for saying it to people?

6. What’s your favorite thing about winter?

portrait of a beautiful woman with a scarf in winter

7. If you had to do one job for the rest of your life, what would you be doing?

8. What’s your favorite movie that never received the praise you believed it deserved?

9. What was your very first job and how long did you last there?

10. What’s your favorite book of all time?

11. In your opinion, what are some really good questions to ask at a job interview that you never got asked?

12. What is your earliest childhood memory?

happy woman smiling on the sofa drinking cofee with her feet on the table

13. In your opinion, what’s the best icebreaker when you’re trying to flirt with an introvert?

14. What is the craziest thing you’ve ever done when it came to love and would you repeat it?

15. Would you consider yourself an introvert or an extrovert?

16. What was the last book that blew your mind and that you simply couldn’t put down?

17. Do you remember the first time you had to be away from home for a long period of time and has it got easier with time?

18. Who’s your favorite ultimate superhero of all time and give me three compelling reasons why (make me change my mind if we’re not on the same page)

young cute couple talking while drinking coffee

19. What’s the weirdest thing you’ve ever eaten and was it for a dare or were you simply feeling adventurous?

20. In your opinion, what’s the worst thing one can do to instigate the end of a long-term relationship right then and there?

21. Which fictional character would you want to be for a day and why?

See also: Should I Block My Ex? These 10 Realizations Will Help You Decide

22. What’s your favorite way of letting someone know that you’re really enjoying their company?

23. Are you into video games and what are your top five choices for a beginner?

24. If you could only eat one type of ice cream forever, which flavor would you choose?

handsome man in a yellow shirt eating icecream

25. What’s your favorite holiday and what’s your favorite way to spend it? Are you into traditions or do you try to switch it up every year?

26. Which reality TV show is your guilty pleasure that you’re too embarrassed to admit to anyone?

27. What’s your go-to way of spending your free time and how often do you do it?

28. What do you consider to be an immediate red flag when on a first date with someone?

29. What’s your favorite place where you go to unwind and simply forget about all your troubles and worries?

30. Which famous person do you think you’d be best friends with if you met them in person and got to know them?

happy female friends having fun in a photo booth

31. If you were offered your absolute dream job with great pay but it would mean having to move to another continent, would you accept it?

32. What kind of person were you in high school and how much have you changed/matured since graduating?

33. What’s your idea of a perfect day with someone you’re really into?

34. What’s your favorite prank you’ve ever pulled on someone from work and how did they react?

35. If you could become a member of any band in the world right now, which one would it be and what would your role in the band be?

boy rock band playing a song in the studio

36. If you had to become an animal for a day, which animal do you think you’d turn into?

37. Who’s the smartest person in your life?

38. When was the last time you called your grandparents (any one of them)?

39. Who knows you best out of all the close people around you?

42. Which language would you love to be fluent in other than those you already speak?

41. What’s the one thing you did and instantly regretted?


man leaving woman on the street after a fight

42. Be honest. How funny do you consider yourself to be?

43. What’s the funniest yet most embarrassing situation you’ve ever found yourself in with your best friend?

44. List three pet peeves and name one of those that you could get over the fastest?

45. What article of clothing do you wish would become trendy again?

46. Are you distantly related to some famous person?

47. Do you like to work out and how do you keep fit?

busy business man in a suit with a tie traveling in a car

48. If you were president, what’s the one law you’d immediately change and what would you do differently to the current president?

49. What are your greatest strengths and where are you lacking?

50. Did you have a favorite teacher in school and who was it?

See also: Sex With Friends? The 10 Biggest Secrets No One Will Tell You

51. If you had a warning label, what would it say?

52. If there was a soundtrack to your life, which five songs would it consist of?

53. Who was your longest crush in high school and did anything ever happen?

cute young highschool couple studying together

54. Which fast-food chain would you love to be the owner of?

55. When did you find out about Santa and how did you react to it?

56. Have you ever had a secret crush on any of your professors?

57. Would you rather be extremely good-looking but not overly intelligent or would you rather be borderline genius but with average looks?

58. You’ve just found out that you’re being shipped to a desert island for a whole month. Which three things are you taking with you?

59. If you could teleport to any place in the world right now, where would you go and who would you take?

handsome man in a white shirt walking in his condo

60. If you were able to change one historical thing (no matter how big or small, it can be literally anything) what would you go back and change?

61. If you had to live for a year in Alaska or Hawaii, which one would you choose and why?

62. How many pairs of shoes are too many?

63. If you could be a superhero for a day, which one would you choose to be and why?

64. What’s the longest you’ve ever been awake?

65. How would your closest friends describe you?

See also: 20 Amazing And Cute Late-Night Date Ideas For All Couples

Deeper Get To Know You Questions

silhouette of a couple talking in the sunset while sitting next to water

In this section, we’ll switch gears and get a little more personal.

For example, you can use these get to know you questions when hanging out with a close friend one on one and you’re trying to get to know them a little bit better!

You can allow yourself to get a little more personal here (depending on how close your friendship is, so choose wisely).

66. What is your most painful childhood memory and how have you been able to cope with it as you got older?

67. What is the most sincere thing you’ve ever done for somebody you loved and how was it received?

68. If your loved one told you they were moving out of the country for a job, would you go with them (if you were invited) or would you break it off?

69. What’s the one thing that bugged you for a really long time that ended up not being that big of a deal in the end?

70. What’s the one thing that you believe everyone is wrong about when it comes to you? Do you ever feel completely misunderstood or not seen?

business man with a phone in his hand driving in the back of a car

71. Have you ever been betrayed by your best friend but ended up forgiving them in the end? How did it change your relationship?

72. How do you deal with certain individuals who you really dislike but you have to remain polite around them?

73. Have you ever been in a dangerous (near-death even) situation and has it affected the way you live your life now?

74. How do you pick yourself up when all you want to do is be left alone and dwell on a really bad situation you’re in?

75. Who’s your strongest support system without whom you couldn’t imagine your life?

76. What is your most valuable possession that means the world to you?

77. Which person from your life has affected your life the most and how?

78. Who is the one person who can make you laugh when all you want to do is cry?

79. Which period of your life has been the most painful and why do you think that is? If you could change anything from that time, would you?

80. Do you find it easy saying goodbye to people who no longer serve you any good?

81. How many things from your bucket list would you actually be willing to do right now?

82. What’s the craziest thing you’ve ever been asked to do by your partner and have you done it?

83. What’s your favorite way of unwinding after a long, stressful day?

woman sitting on a couch and enjoying cup of fresh cofee

84. Have you ever experienced the ultimate horrible first date and who was to blame?

85. When was the last time you told someone exactly what you wanted to say even though it was really harsh (but truthful and necessary)?

86. Do you avoid conflict as much as possible or are you a straightforward type of person who’ll get into it with anyone if necessary?

87. What is your relationship with your parents like and how has it changed or evolved over the years? Are you close and do you like spending time with them?

88. What’s the deal with your siblings? Are you close and do you see each other a lot? If they live far away, do you keep in touch?

See also: The Ultimate List Of Fake Love Quotes And Sayings

89. How do you think you’re doing in life in general? How happy are you and what would you change about your life if you could right now?

90. If your friends could change one thing about you, what do you think that would be? (Be honest!)

91. What qualities do you think your friends value most about you?

92. What is the most embarrassing drunken mishap that you’ve ever gotten yourself into?

93. Have you ever lied to someone about something important in order to have your way and who was it (if you’re willing to divulge)?

94. Do you tend to judge a book by its cover and have you ever tried to change that?

95. Which bad quality do you hate about yourself but you don’t think you’ll ever be able to change?

sad, depressed man in a white shirt sitting in the dark

96. What’s your stance on marriage? Would you do it and do you think you’d be able to make it last?

97. What would your ex-partner say about your break-up? Are you on the same page about the reason you broke up or was it anything but amicable?

98. What is the most thoughtful present you’ve ever received and who was it from?

99. When your friends seek your advice, what is it usually in regards to?

100. Who’s your go-to person for literally anything?

101. Do you think your friends truly love you for who you are?

102. If you could switch places with one person from your life and be them for a week, who would it be?

103. What qualities do you appreciate the most about people?

104. What do you find most annoying about your best friend?

105. What’s your most prized family memory that immediately makes you feel nostalgic?

106. What’s the easiest way to get on your nerves and who’s the master of it?

angry and annoyed woman with orange scarf in the street

107. If your life story had a name, what would it be?

See also: Hiding From The World: 5 Ways You’re Doing It And How To Be Seen

108. Which three people would you take with you if you were moving out of the country permanently?

109. What piece of advice would you give your teenage self?

110. Which risk would you be willing to take if it was for someone you really loved?

111. What’s the worst thing you’ve done to another human being and why?

112. What is your biggest regret so far in life?

113. What would your family say are your best and worst qualities?

114. Have you ever been cheated on and did you forgive?

115. Would you rather be remembered for being a very kind and pleasant person or for some type of big accomplishment?

See also: 182 Hardest Questions To Answer And Ask Someone

Most Personal Get To Know You Questions

cute young couple having a conversation on the balcony

This section is reserved for those you’ve developed a very close and personal relationship with, like a boyfriend/girlfriend, really close friend and/or family members.

People you’ve been around for a long time and who wouldn’t be offended by these get to know you questions.

There are some really tricky and personal ones here so pick and choose when to use each one.

See also: How To Live In Peace And Harmony With The Help Of These 5 Steps

116. Were you ever a bully in high school? Were you ever the one bullied?

117. What has been your biggest mistake when it comes to your dating life that you fear will never allow you to find your one true love?

118. How do you think you’ve ever sabotaged your own life?

119. Do you fear death? Have you ever wondered about what it would feel like to hurt yourself?

120. What, in your opinion, do you believe to be the most shocking thing for people to discover about you?

black and white picture of a handsome shirtless man on the beach

121. Have you ever cheated on somebody and can you share the reasons which led to that?

122. What would it take for you to leave a person you love and never look back?

123. Have you ever dumped someone for really selfish reasons but lied that it was about something else?

124. Are you happy? Do you love yourself?

125. When is the last time you felt truly, deeply content without anything weighing you down?

126. Does anyone really know the real you? The person you are when no one’s looking?

127. Have you ever burned a bridge that you regretted later on?

128. Are you a genuine person?

129. What’s your worst fear that you’ve never told anyone?

130. What would it take for you to just up and leave without saying goodbye to anyone?

woman on the phone with suitcase in her room

131. Would you rather win a million dollars right now or find the love of your life?

132. Can people depend on you?

133. Have you been through a lot in life?

134. Do you truly, genuinely love your family?

135. Would you be someone else if you could?

136. Who is the person who gives your life meaning?

137. What has been the most heartbreaking yet most valuable life lesson you’ve learned in life?

138. Does anyone know your worst secrets?

139. Do you find it easy to lie?

140. How often do you resort to lying in order to get what you want?

woman comforting her sad friend on a couch

141. If you could have a complete do-over of your life, what would you change and why?

142. Which is your go-to song for when you’re feeling broken?

143. Is there anyone you hate?

144. Is there anyone in your life you wish you could get rid of but can’t for some reason?

145. What do you believe to be the meaning of life?

146. Have you ever hit rock-bottom and how did you get out of it?

147. Do you look up to your parents’ marriage?

148. What makes you feel alive?

149. Can you forgive easily?

150. What has been the most defining chapter of your life?

See also: 12 Sexy Body Language Signs That Make You Irresistible To Men

Final Words

serious couple sitting on a bench and talk in the park

Good luck with these get to know you questions and remember that each section serves a particular purpose.

The first section is the perfect icebreaker for when you’re trying to get to know someone but don’t want to pry.

The second section contains some deeper questions that you can ask someone you’re pretty close to already.

And lastly, the third section contains get to know you questions of the most intimate nature.

Reserve those for people you’ve become truly close to where there are zero constraints.

I’m sure you’ll be able to recognize which questions are best suited for your needs and hopefully they’ll serve their purpose.

Have fun and good luck bonding and exploring!

A Collection Of Getting To Know You Questions For A Deeper Insight