Thought Catalog

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

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Knocked Up (Unrated Widescreen Edition)
Knocked Up (Unrated Widescreen Edition)

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 try to get every person I interact with to say, Wow. That’s a great 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 chatting with so I can artfully select a question that pushes them to lean into an area of their brain they don’t normally hang out in. To turn a flashlight on in the halls of their head and search for an answer to a question they never imagined they’d have to answer.

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

Why do I play this silly game?

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

I thought it would be fun (and hopefully valuable) to give you a sneak peak at some of my favorites to ask (especially on first dates or with partners). Typically I ask questions based off of the conversation at hand but if I’m needing a great one to start 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. Quit wasting it asking things you don’t really 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 try to guess which one is a lie.

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

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

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

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

6. What’s an accomplishment you are really 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 fun way).

10. When it comes to love and relationships, what is the first lesson you want to teach your children?

11. If you could change 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 giving up?

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

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

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

19. What do you want to be known for?

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

21. Complete 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 happy 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 experience teach you?

24. What’s something that comes easier 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 90 percent of the population?

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

28. What is a piece of advice you often give but find yourself struggling to follow?

29. Describe your perfect 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 happy are you? (Then sit silent and wait for their answer. The pause is important).

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 biggest impact on you and why?

39. What is a piece 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 impact on you or an ah-ha moment?

42. If you only had 30 seconds to share one if the most important 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 probably make again?

45. When was the last time life left you breathless? TC mark

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Read more books in 2018…

Cut yourself some slack. One of the biggest regrets most people have about their 20s is that they didn’t enjoy them more. And I’m not talking about “buy more expensive dinners, take another trip to Thailand” type of enjoyment. I mean having the ability to take a deep breath and sip coffee in the morning knowing that you have done, and are doing, your best.

“These essays are slowly changing my life, as the title promises. As my friends’ birthday come along, they will all be receiving a copy of this wonderful book.” – Janie

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