Thought Catalog

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

  • 0
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

Powered by Revcontent

Poetry Lovers! 💖

Love a soft person. The ones who are positive, even in the worst of circumstances. Someone whose strength is not in bravado, but in their quiet. Someone who is strong for others because that is what is needed in that moment. Someone who is the moon that soothes instead of the sun that burns. Someone who sees the very best in people even when you think they aren’t worth it. The kind of person who always wants to do the best for those they love.”

“I bought this on a whim to read as I was resting for the night, and I do not regret it one bit! Everything about the poetry in this book is amazing, heart breaking, and soul searching. It will lift your spirits on your darkest days. I want to thank the author so much for writing this, as it’s something I will be rereading a lot! Always remember, everything about you is important. You matter.” —McKayla

Click to heal your heart

More From Thought Catalog

45 Questions To Guarantee You’ll Never Have A Boring Date Again is cataloged in , ,
  • https://thoughtcatalog.com/emma-golden/2014/09/6-power-moves-girls-need-to-pull-if-they-want-a-real-relationship/ 6 Power Moves Girls Need To Pull If They Want A Real Relationship | Thought Catalog

    […] What Your Drink Says About You Read this: 5 Things Every Girl Looking For Love Should Stop Doing Read this: 45 Questions To Guarantee You’ll Never Have A Boring Date Again Cataloged […]

  • http://flawedtwenties.wordpress.com Lyla Michaels

    Reblogged this on Conversations I Wish I Had.

  • http://marredconversationalists.wordpress.com/2014/11/03/45-questions-to-guarantee-youll-never-have-a-boring-date-again/ 45 Questions To Guarantee You’ll Never Have A Boring Date Again | Conversations I Wish I Had
  • https://thoughtcatalog.com/christopher-hudspeth/2014/04/18-ugly-truths-about-modern-dating-that-you-have-to-deal-with/ 18 Ugly Truths About Modern Dating That You Have To Deal With | Thought Catalog

    […] Read this: 45 Questions To Guarantee You’ll Never Have A Boring Date Again Read this: 6 Power Moves Girls Need To Pull If They Want A Real Relationship Read this: Ladies, Please Stop Doing This On Instagram Read this: 50 Women On “Does Dick Size Matter?” Read this: 60 Uncommon Things Men Find Attractive About Women […]

  • http://VSCPskylargarfield.wordpress.com vscpskylargarfield

    Reblogged this on Skylar Garfield.

  • http://heykendra.com/45-questions-guarantee-youll-never-boring-date/ 45 Questions To Guarantee You’ll Never Have A Boring Date Again - HEY KENDRA

    […] post was first released on Thought Catalog. Amazing bike photo via Jessica […]

  • http://arab258.wordpress.com arab258

    Reblogged this on emelizabethj.

  • http://sphtc.wordpress.com keiarabranch
  • http://coffeewithalex.wordpress.com alexrandya

    Reblogged this on Coffee with Alex.

  • http://roaringtwentysblog.wordpress.com/2015/01/12/one-day/ One Day. | Roaring Twentys

    […] was recently reading an article on the Thought Catalog (see here), and it got me thinking. The article had a list of questions to ask on a potential date. All were […]

  • http://silverstories.dk/2015/01/links-i-liked-in-january/ Links I liked in January silverstories blog

    […] ♥ 45 questions to guarantee you’ll never have a boring date again – 45 pretty interesting questions from ThoughtCatalog one could also ask oneself. […]

  • http://jstewart3blog.wordpress.com anonymous
  • Abhinav

    Reblogged this on Abhinav's Blog of Reblogs.

  • http://th3goodlife.com Lerozier

    Reblogged this on Th3 Good Life and commented:
    Meeting new people is all about making that person a new experience in your life and with these questions you are able to do that. This is awesome.

  • https://allthebestofmeasneverbefore.wordpress.com/2016/01/06/december-232015/ December 23,2015 | The Vibrant Red

    […] https://thoughtcatalog.com/kendra-wright/2014/11/45-questions-to-guarantee-youll-never-have-a-boring-… If you win a big amount of cash like a million dollars, what would you do first? […]

  • https://findingtheingridientinlife.wordpress.com/2016/01/10/what-my-subconscious-tells-me-about-myself/ What My Subconscious Tells Me About Myself | findingtheingridientinlife

    […] I read tons of random articles and I happened to stumble up on stumble upon ironically an article 45 Questions To Guarantee You’ll Never Have A Boring Date Again  and I thought to myself let me save that just in case I need it someday. Well. I used it.  He […]

  • http://lincolnfit1.com/escort-services-can-be-very-good-for-single-dudes/ Escort services can be very good for single dudes – Lincoln Fit

    […] lot of people simply want to be with a woman without putting up with boring dates. If you have a job that will require a lot of your time then this is especially true. The demands […]

  • https://sillymetamorphosis.wordpress.com/2016/07/14/interviewing-the-bored-author/ Interviewing the Bored Author – Silly Metamorphosis

    […] set of questions which I found on google were originally meant for two people who wants to break the ice when they’re out on a date or […]

  • http://www.abelabel.com/2017/07/45-questions-guarantee-youll-never-boring-date/ 45 Questions To Guarantee You’ll Never Have A Boring Date | Abel Abel

    […] (Source : Thought Catalog) […]

  • http://itsmilapeti.com/2017/08/20/45questionschallenge-part-1/ #45QuestionsChallenge – Part 1 – it's milapeti

    […] took this questions from a post Kendra Wright wrote. You are supposed to ask them to a date or whatever, but I’ll answer all […]

blog comments powered by Disqus