45 Questions To Ensure You’ll Never Have A Boring Date Again, Thought Catalog

45 Questions To Assure You’ll Never Have A Boring Date Again

I have a secret game that I play in every conversation I have. Until now, no one knew about it… but I’m about to dish the deets. 😉

I attempt to get every person I interact with to say, Wow. That’s a fine question… at least once in our conversation.

To win at this game, I have to stay super present and plugged in to who I’m talking with so I can artfully select a question that shoves them to lean into an area of their brain they don’t normally suspend out in. To turn a flashlight on in the halls of their head and search for an response to a question they never imagined they’d have to response.

It’s fascinating watching them dig deeper into who they are. To practice them introspectively retreat for a few moments and rummage through their noggin’ for the reaction.

Why do I play this ditzy game?

Because I believe it’s our responsibility to detect something awesome every person we meet. If we don’t, it cheats both parties out of a cool practice.

I thought it would be joy (and hopefully valuable) to give you a sneak peak at some of my favorites to ask (especially on very first dates or with fucking partners). Typically I ask questions based off of the conversation at mitt but if I’m needing a good one to commence with, I always have some top notch options stashed in my skull in a must-break-glass emergency 😉

My hope is that you too can tuck this list in your back pocket and together we can rid this planet of all the effortless and boring questions people ask each other these days. Seriously… palm, meet face.

Every breath you take is killing you. Abandon wasting it asking things you don’t indeed care about any way. 😉

Here’s some of the favs on my hit list:

1. Ask them to give you two “truths” and a lie. Then attempt to guess which one is a lie.

Two. If you could write a note to your junior self, what would you say in only two words?

Three. If you had to name one thing that truly makes your day, what would it be?

Four. What is a misconception others often have about you?

Five. Whats the most valuable life lesson you have learned because of a mistake?

6. What’s an accomplishment you are truly proud of?

7. Read anything interesting lately?

8. What’s one thing you wish you had known as a freshman in college?

9. What is one day you would love to relive? (This will tell you something near and dear to your their heart in a joy way).

Ten. When it comes to love and relationships, what is the very first lesson you want to train your children?

11. If you could switch one physical & non physical thing about yourself, what would it be?

12. What should I know about you that I’d never think to ask about?

13. What do you hate most about the dating process? (You want them to tell you so you can avoid it) 😉

14. What is #1 thing in your life that you are not doing that you wish you were?

15. What do you do when you feel like providing up?

16. If you could only keep one book you presently own, what would it be?

17. What are you most excited about in your life right now?

Legitimate. Describe one extravagance you have for which you will never apologize.

Nineteen. What do you want to be known for?

20. In one sentence what is your thickest concern right now?

21. Finish the following: There would be fewer divorces in this country if only people ________.

22. What’s something that you sometimes outwardly wish more people realized about you, but you’re glad is internalized because to be able to sit on this information makes you stronger?

23. How many times have you been in love & what did each practice train you?

24. What’s something that comes lighter to you than it does for most?

25. What do you feel people take for granted the most?

26. What are you better at than ninety percent of the population?

27.What is something about you that would surprise me?

28. What is a chunk of advice you often give but find yourself fighting to go after?

29. Describe your ideal mate in one sentence.

30. When is the last time you did something courageous for yourself?

31. On a scale of one to ten, how blessed are you? (Then sit silent and wait for their response. The pause is significant).

32. Whats the stupidest thing you’ve ever done for love?

33. What’s something many people fear that doesn’t scare you at all?

34. What’s something that instantly makes someone less attractive?

35. Would you describe yourself as more of an optimist, a pessimist, or a realist?

36. What would be a question you’d be afraid to tell the truth on?

37. What is something you wish you did more of in your life and something you wish you did less of?

38. Which significant other in your life has had the thickest influence on you and why?

39. What is a lump of advice that you were given that if you listened to it, you would not be where you are today?

40. If you had to spend a year alone with one other person who would it be and why?

41. What was the last thing you learned that made a big influence on you or an ah-ha moment?

42. If you only had thirty seconds to share one if the most significant things you’ve learned with the world, what would it be?

43. What’s one fear you know is holding you back?

44. What was the last mistake you made that you’re sure you’ll very likely make again?

45. When was the last time life left you panting?

45 Questions To Ensure You’ll Never Have A Boring Date Again, Thought Catalog

45 Questions To Assure You’ll Never Have A Boring Date Again

I have a secret game that I play in every conversation I have. Until now, no one knew about it… but I’m about to dish the deets. 😉

I attempt to get every person I interact with to say, Wow. That’s a good question… at least once in our conversation.

To win at this game, I have to stay super present and plugged in to who I’m talking with so I can artfully select a question that thrusts them to lean into an area of their brain they don’t normally dangle out in. To turn a flashlight on in the halls of their head and search for an reaction to a question they never imagined they’d have to response.

It’s fascinating watching them dig deeper into who they are. To practice them introspectively retreat for a few moments and rummage through their noggin’ for the reaction.

Why do I play this foolish game?

Because I believe it’s our responsibility to detect something awesome every person we meet. If we don’t, it cheats both parties out of a cool practice.

I thought it would be joy (and hopefully valuable) to give you a sneak peak at some of my favorites to ask (especially on very first dates or with fucking partners). Typically I ask questions based off of the conversation at forearm but if I’m needing a good one to commence with, I always have some top notch options stashed in my skull in a must-break-glass emergency 😉

Every breath you take is killing you. Abandon wasting it asking things you don’t indeed care about any way. 😉

Here’s some of the favs on my hit list:

1. Ask them to give you two “truths” and a lie. Then attempt to guess which one is a lie.

Two. If you could write a note to your junior self, what would you say in only two words?

Three. If you had to name one thing that indeed makes your day, what would it be?

Four. What is a misconception others often have about you?

Five. Whats the most valuable life lesson you have learned because of a mistake?

6. What’s an accomplishment you are truly proud of?

7. Read anything interesting lately?

8. What’s one thing you wish you had known as a freshman in college?

9. What is one day you would love to relive? (This will tell you something near and dear to your their heart in a joy way).

Ten. When it comes to love and relationships, what is the very first lesson you want to train your children?

11. If you could switch one physical & non physical thing about yourself, what would it be?

12. What should I know about you that I’d never think to ask about?

13. What do you hate most about the dating process? (You want them to tell you so you can avoid it) 😉

14. What is #1 thing in your life that you are not doing that you wish you were?

15. What do you do when you feel like providing up?

16. If you could only keep one book you presently own, what would it be?

17. What are you most excited about in your life right now?

Legal. Describe one extravagance you have for which you will never apologize.

Nineteen. What do you want to be known for?

20. In one sentence what is your thickest concern right now?

21. Finish the following: There would be fewer divorces in this country if only people ________.

22. What’s something that you sometimes outwardly wish more people realized about you, but you’re glad is internalized because to be able to sit on this information makes you stronger?

23. How many times have you been in love & what did each practice instruct you?

24. What’s something that comes lighter to you than it does for most?

25. What do you feel people take for granted the most?

26. What are you better at than ninety percent of the population?

27.What is something about you that would surprise me?

28. What is a lump of advice you often give but find yourself fighting to go after?

29. Describe your ideal mate in one sentence.

30. When is the last time you did something courageous for yourself?

31. On a scale of one to ten, how glad are you? (Then sit silent and wait for their response. The pause is significant).

32. Whats the stupidest thing you’ve ever done for love?

33. What’s something many people fear that doesn’t scare you at all?

34. What’s something that instantly makes someone less attractive?

35. Would you describe yourself as more of an optimist, a pessimist, or a realist?

36. What would be a question you’d be afraid to tell the truth on?

37. What is something you wish you did more of in your life and something you wish you did less of?

38. Which significant other in your life has had the largest influence on you and why?

39. What is a chunk of advice that you were given that if you listened to it, you would not be where you are today?

40. If you had to spend a year alone with one other person who would it be and why?

41. What was the last thing you learned that made a big influence on you or an ah-ha moment?

42. If you only had thirty seconds to share one if the most significant things you’ve learned with the world, what would it be?

43. What’s one fear you know is holding you back?

44. What was the last mistake you made that you’re sure you’ll very likely make again?

45. When was the last time life left you choky?

45 Questions To Ensure You’ll Never Have A Boring Date Again, Thought Catalog

45 Questions To Assure You’ll Never Have A Boring Date Again

I have a secret game that I play in every conversation I have. Until now, no one knew about it… but I’m about to dish the deets. 😉

I attempt to get every person I interact with to say, Wow. That’s a superb question… at least once in our conversation.

To win at this game, I have to stay super present and plugged in to who I’m talking with so I can artfully select a question that shoves them to lean into an area of their brain they don’t normally drape out in. To turn a flashlight on in the halls of their head and search for an response to a question they never imagined they’d have to response.

It’s fascinating watching them dig deeper into who they are. To practice them introspectively retreat for a few moments and rummage through their noggin’ for the reaction.

Why do I play this stupid game?

Because I believe it’s our responsibility to detect something awesome every person we meet. If we don’t, it cheats both parties out of a cool practice.

I thought it would be joy (and hopefully valuable) to give you a sneak peak at some of my favorites to ask (especially on very first dates or with playmates). Typically I ask questions based off of the conversation at arm but if I’m needing a fine one to commence with, I always have some top notch options stashed in my skull in a must-break-glass emergency 😉

Every breath you take is killing you. Abandon wasting it asking things you don’t indeed care about any way. 😉

Here’s some of the favs on my hit list:

1. Ask them to give you two “truths” and a lie. Then attempt to guess which one is a lie.

Two. If you could write a note to your junior self, what would you say in only two words?

Trio. If you had to name one thing that truly makes your day, what would it be?

Four. What is a misconception others often have about you?

Five. Whats the most valuable life lesson you have learned because of a mistake?

6. What’s an accomplishment you are truly proud of?

7. Read anything interesting lately?

8. What’s one thing you wish you had known as a freshman in college?

9. What is one day you would love to relive? (This will tell you something near and dear to your their heart in a joy way).

Ten. When it comes to love and relationships, what is the very first lesson you want to train your children?

11. If you could switch one physical & non physical thing about yourself, what would it be?

12. What should I know about you that I’d never think to ask about?

13. What do you hate most about the dating process? (You want them to tell you so you can avoid it) 😉

14. What is #1 thing in your life that you are not doing that you wish you were?

15. What do you do when you feel like providing up?

16. If you could only keep one book you presently own, what would it be?

17. What are you most excited about in your life right now?

Legal. Describe one extravagance you have for which you will never apologize.

Nineteen. What do you want to be known for?

20. In one sentence what is your largest concern right now?

21. Accomplish the following: There would be fewer divorces in this country if only people ________.

22. What’s something that you sometimes outwardly wish more people realized about you, but you’re blessed is internalized because to be able to sit on this information makes you stronger?

23. How many times have you been in love & what did each practice train you?

24. What’s something that comes lighter to you than it does for most?

25. What do you feel people take for granted the most?

26. What are you better at than ninety percent of the population?

27.What is something about you that would surprise me?

28. What is a lump of advice you often give but find yourself fighting to go after?

29. Describe your flawless mate in one sentence.

30. When is the last time you did something courageous for yourself?

31. On a scale of one to ten, how blessed are you? (Then sit silent and wait for their response. The pause is significant).

32. Whats the stupidest thing you’ve ever done for love?

33. What’s something many people fear that doesn’t scare you at all?

34. What’s something that instantly makes someone less attractive?

35. Would you describe yourself as more of an optimist, a pessimist, or a realist?

36. What would be a question you’d be afraid to tell the truth on?

37. What is something you wish you did more of in your life and something you wish you did less of?

38. Which significant other in your life has had the fattest influence on you and why?

39. What is a chunk of advice that you were given that if you listened to it, you would not be where you are today?

40. If you had to spend a year alone with one other person who would it be and why?

41. What was the last thing you learned that made a big influence on you or an ah-ha moment?

42. If you only had thirty seconds to share one if the most significant things you’ve learned with the world, what would it be?

43. What’s one fear you know is holding you back?

44. What was the last mistake you made that you’re sure you’ll very likely make again?

45. When was the last time life left you panting?

45 Questions To Ensure You’ll Never Have A Boring Date Again, Thought Catalog

45 Questions To Ensure You’ll Never Have A Boring Date Again

I have a secret game that I play in every conversation I have. Until now, no one knew about it… but I’m about to dish the deets. 😉

I attempt to get every person I interact with to say, Wow. That’s a superb question… at least once in our conversation.

It’s fascinating watching them dig deeper into who they are. To practice them introspectively retreat for a few moments and rummage through their noggin’ for the response.

Why do I play this foolish game?

Because I believe it’s our responsibility to detect something awesome every person we meet. If we don’t, it cheats both parties out of a cool practice.

I thought it would be joy (and hopefully valuable) to give you a sneak peak at some of my favorites to ask (especially on very first dates or with fucking partners). Typically I ask questions based off of the conversation at forearm but if I’m needing a fine one to embark with, I always have some top notch options stashed in my skull in a must-break-glass emergency 😉

Every breath you take is killing you. Abandon wasting it asking things you don’t indeed care about any way. 😉

Here’s some of the favs on my hit list:

1. Ask them to give you two “truths” and a lie. Then attempt to guess which one is a lie.

Two. If you could write a note to your junior self, what would you say in only two words?

Three. If you had to name one thing that truly makes your day, what would it be?

Four. What is a misconception others often have about you?

Five. Whats the most valuable life lesson you have learned because of a mistake?

6. What’s an accomplishment you are truly proud of?

7. Read anything interesting lately?

8. What’s one thing you wish you had known as a freshman in college?

9. What is one day you would love to relive? (This will tell you something near and dear to your their heart in a joy way).

Ten. When it comes to love and relationships, what is the very first lesson you want to instruct your children?

11. If you could switch one physical & non physical thing about yourself, what would it be?

12. What should I know about you that I’d never think to ask about?

13. What do you hate most about the dating process? (You want them to tell you so you can avoid it) 😉

14. What is #1 thing in your life that you are not doing that you wish you were?

15. What do you do when you feel like providing up?

16. If you could only keep one book you presently own, what would it be?

17. What are you most excited about in your life right now?

Legal. Describe one extravagance you have for which you will never apologize.

Nineteen. What do you want to be known for?

20. In one sentence what is your fattest concern right now?

21. Accomplish the following: There would be fewer divorces in this country if only people ________.

22. What’s something that you sometimes outwardly wish more people realized about you, but you’re blessed is internalized because to be able to sit on this information makes you stronger?

23. How many times have you been in love & what did each practice instruct you?

24. What’s something that comes lighter to you than it does for most?

25. What do you feel people take for granted the most?

26. What are you better at than ninety percent of the population?

27.What is something about you that would surprise me?

28. What is a chunk of advice you often give but find yourself fighting to go after?

29. Describe your ideal mate in one sentence.

30. When is the last time you did something courageous for yourself?

31. On a scale of one to ten, how glad are you? (Then sit silent and wait for their reaction. The pause is significant).