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When you want to get to know someone better or improve an existing relationship, knowing the best
questions to ask—from simple getting-to-know-you questions to deep questions about life—can help
you take your conversation to a deeper level.
So whether you're looking for deep questions to ask a guy or girl or need good questions to get to
know someone new, these 275+ deep personal questions to ask will help you break past the surface
and strengthen your connection.
CONTENTS
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5/21/23, 5:27 PM 275+ Deep Questions To Ask To Get to Know Someone - Parade: Entertainment, Recipes, Health, Life, Holidays
3. What form of public transportation do you prefer? (air, boat, train, bus, car, etc.)
5. What two radio stations do you listen to in the car the most?
6. If you could hire someone to help you, would it be with cleaning, cooking, or yard work?
15. If you could choose to do anything for a day, what would it be?
18. If you could choose to do anything for a day, what would it be?
19. Would you rather win the lottery or work at the perfect job? And why?
23. Would you rather ride a bike, ride a horse, or drive a car?
24. In the evening, would you rather play a game, visit a relative, watch a movie, or read?
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5/21/23, 5:27 PM 275+ Deep Questions To Ask To Get to Know Someone - Parade: Entertainment, Recipes, Health, Life, Holidays
26. If you could only eat one meal for the rest of your life, what would it be?
30. Which would you rather do: wash dishes, mow the lawn, clean the bathroom, or vacuum the
house?
32. Would you rather win the lottery or work at the perfect job? And why?
36. If you could go back in time to change one thing, what would it be?
37. If you could share a meal with any 4 individuals, living or dead, who would they be?
39. What's the longest you've gone without sleep (and why)?
40. What's the tallest building you've been to the top in?
41. What was the last movie you went to? What did you think?
46. If you could go back in time, what year would you travel to?
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5/21/23, 5:27 PM 275+ Deep Questions To Ask To Get to Know Someone - Parade: Entertainment, Recipes, Health, Life, Holidays
48. Aside from necessities, what one thing could you not go a day without?
Related: 250 Newlywed Game Questions and 250 Deep Conversation Topics
9. How do you feel about sharing your password with your partner?
11. Would you still love your spouse if they were diagnosed with a terminal disease?
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5/21/23, 5:27 PM 275+ Deep Questions To Ask To Get to Know Someone - Parade: Entertainment, Recipes, Health, Life, Holidays
15. What is the craziest thing you’ve ever done and would you do it again?
16. If a genie granted you 3 wishes right now, what would you wish for?
18. What’s the one thing you would like to change about yourself?
23. Is what you’re doing now what you always wanted to do growing up?
25. If you are in a bad mood, do you prefer to be left alone or have someone to cheer you up?
26. What’s the one thing that people always misunderstand about you?
28. When was the last time you broke someone’s heart?
34. Who is that one person you can talk to about just anything?
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5/21/23, 5:27 PM 275+ Deep Questions To Ask To Get to Know Someone - Parade: Entertainment, Recipes, Health, Life, Holidays
37. Would you take on your significant other's religion if they had one?
39. What’s been your biggest mistake so far in life and what did you learn from it?
44. What would you do if your parents didn’t like your partner?
46. What’s your favorite book/movie of all time and why did it speak to you so much?
52. If you could be a woman for a day, what would you do?
3. What’s something you learned recently that you really should have already known?
4. What was something you ate regularly as a child but now cringe at the thought of eating?
5. If you were an action figure, what accessories would you be sold with?
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5/21/23, 5:27 PM 275+ Deep Questions To Ask To Get to Know Someone - Parade: Entertainment, Recipes, Health, Life, Holidays
7. Do you prefer being warmed when you’re too cold or being cooled when you’re too hot?
9. Is flirting cheating?
10. If you were given $15,000 to give the most amount of happiness to the most amount of people,
what would you do?
11. What piece of culture or trend has died out, but you would like to see it make a comeback?
13. What kinds of things are normal now but will be highly valued antiques a century later?
14. What’s the best practical joke you’ve pulled or seen pulled?
16. If you inherited a private jet from a stranger, what would you do with it?
18. What’s an innocent mistake you made that had dramatic consequences?
19. Have you ever trusted your boyfriend to buy clothes for you?
20. What’s something weird that you recommend everyone trying at least once?
21. What country can you name but besides the name you know almost nothing else about it?
25. What’s something horrible that we as humans have accepted, because that’s just how things are;
but actually things don’t have to be that way at all?
26. If you could hear every time someone said something good about you or something negative
about you, which would you choose?
27. What do you think people automatically assume about you when they look at you?
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5/21/23, 5:27 PM 275+ Deep Questions To Ask To Get to Know Someone - Parade: Entertainment, Recipes, Health, Life, Holidays
28. Looking back on your life, what have you done that has given you the most satisfaction?
29. What’s the best gag gift you’ve ever seen or gotten?
30. When was the last time you laughed so hard you cried?
31. What would you do if your parents didn’t like your partner?
32. If you were forced to create a new dance move, what would it be and what would you call it?
36. If everything was quantified, what life stats would like to see for yourself?
37. What do you really wish you knew when you were younger?
40. What songs can you sing that I’ll know after hearing two words from the song?
41. If you were given $20,000, but it could only be used to upgrade your shower or bathtub what
upgrades would you make?
42. When was the last time you had a gut feeling about something that turned out to be correct? How
about a time your gut feeling was wrong?
44. What’s the biggest lie that a guy has told you?
45. What would you do if one day you woke up and every person was just gone without a trace?
46. What body feature do you pay the most attention to?
49. If you could dedicate your life to solving one problem, what problem would you choose?
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5/21/23, 5:27 PM 275+ Deep Questions To Ask To Get to Know Someone - Parade: Entertainment, Recipes, Health, Life, Holidays
50. What was the worst phase you went through in life?
1. What’s the spiciest thing you’ve eaten? Would you ever eat it again?
3. Which fictional villain made you feel real hatred towards them?
4. What habit do you have that you think not many other people have?
8. What names were ruined for you because you knew someone terrible with that name?
9. What’s the best conspiracy theory you can make up on the spot?
11. What gross and unhygienic things do people do that bothers you?
12. What was the best thing about how your parents raised you?
14. If when you died, you got put into a room for eternity with people who died the same way, how
would you want to die?
15. What would an amusement park filled with your biggest fears be like? What rides would it have?
18. What are the two biggest lessons you’ve learned from previous relationships?
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5/21/23, 5:27 PM 275+ Deep Questions To Ask To Get to Know Someone - Parade: Entertainment, Recipes, Health, Life, Holidays
20. If you could switch genders for a length of time of your choosing, would you? And if so, how long?
23. If you could choose the next president of the United States, who would it be?
24. What’s the most stress relieving thing you can get/do for less than $20?
25. What’s something you wish you had never learned how it was made or how it works?
28. What crazy things will you do if you ever become rich?
29. If you were forced into a dance competition, what song would you choose to dance to?
30. You have unlimited wishes but every time you make a wish what you love most is erased from the
world. How many wishes do you make and what do you wish for? (No, you can’t wish not to have
things erased from the world.)
33. What scrambles your brain every time you think about it?
34. What’s the weirdest wrong number text or phone call you’ve gotten?
37. If you could change your first name, what would be the most epic name you could choose?
40. How often do you go into a room and forget why you went into the room?
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5/21/23, 5:27 PM 275+ Deep Questions To Ask To Get to Know Someone - Parade: Entertainment, Recipes, Health, Life, Holidays
41. What is the strongest animal you could win against with just your bare hands and feet?
42. What event from the past do you most want to see a recording of?
43. What would an amusement park designed specifically to make you happy, be like?
44. What is something you probably should do, but will never do?
45. What great idea would you like to try if you had enough money?
46. If you were in a high-speed chase, what song would you want blaring on the radio?
47. If you had to choose country music or rap, which would you choose?
48. If you could only eat pizza or tacos, which would you choose?
49. If you were given immortality, but there was one condition, what would stop you from accepting
immortality?
53. Are you still friends with anyone from high school?
55. If you could be someone else for a day, who would it be and why?
59. What's the craziest thing you've ever done for a friend?
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5/21/23, 5:27 PM 275+ Deep Questions To Ask To Get to Know Someone - Parade: Entertainment, Recipes, Health, Life, Holidays
4. How do you feel about sharing your password with your partner?
5. What is the craziest thing you’ve ever done and would you do it again?
6. If a genie granted you 3 wishes right now, what would you wish for?
12. What’s the one thing that people always misunderstand about you?
14. If you could change one thing about yourself what would it be?
16. When was the last time you broke someone’s heart?
https://parade.com/1043059/marynliles/deep-questions/ 12/14
5/21/23, 5:27 PM 275+ Deep Questions To Ask To Get to Know Someone - Parade: Entertainment, Recipes, Health, Life, Holidays
26. Is what you’re doing now what you always wanted to do growing up?
31. What are three things you value most about a person?
34. Who is that one person you can talk to about just anything?
36. If you are in a bad mood, do you prefer to be left alone or have someone to cheer you up?
37. What’s the most exciting thing that’s happened this past year?
40. What’s one thing that bothers you most about the world today?
45. What’s your favorite book/movie of all time and why did it speak to you so much?
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47. What’s the one thing you would like to change about yourself?
48. What would you do if you found out you were adopted?
49. What if you found out that you were the star of the Truman Show?
53. What do you think are the most important qualities in a friend?
Check out...
For more fun, deep questions to ask, check out these 250 conversation-starters and interesting
questions that'll keep your convo going.
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