20 Unique Date Night Questions

In my previous life, I was moonlighting as a freelance writer for Modern Socialite, a Calgary-based lifestyle website. My gig included recruiting, interviewing and writing about bachelors in the city.

It was a tough job but someone had to do it 😉

There was the former NHL player, firefighter, successful entrepreneur, mysterious photographer, young philanthropist

Side Note: I was in a relationship at that time so sorry, no grandiose love story about how I ended up dating one of the bachelors. 

After each interview, it was an enjoyable and entertaining experience for both the bachelor and myself.

The conversation was light, fun and exciting …. that should be the objective of any date in the courtship phase.

But we get caught up with trying to dissect past relationships, discuss superficial topics and divulge relationship intentions … that we end up emotionally exhausted and turned off by an answer that would have been otherwise responded in a more authentic way under a less stressful situation.

Instead, try out some or all of these twenty questions the next time you’re on a date and see how the interaction, vibe and end result will differ from previous dates.

  1. What are your three non­-negotiable traits/attributes?
  2. Do you prefer to approach a woman/man or be approached?
  3. What can a woman/man say/do to make you run the other way?
  4. What is the most irresistible thing a woman/man can do?
  5. Who is your celebrity crush?
  6. Which couple inspires you the most?
  7. What is the best relationship advice you have received?
  8. Who is your best friend?
  9. What was your dream job as a kid?
  10. What was your favourite Saturday morning cartoon?
  11. How would your friends describe you?
  12. I am most passionate about ________________________.
  13. Who is your hero/mentor?
  14. What is something that most people would be surprised to learn about you?
  15. Describe your proudest personal/professional accomplishment.
  16. What do you hope to achieve in the next three years?
  17. If you could have any super power, what would it be?
  18. If you are stuck on an island, what are three things you must have?
  19. Name three people (dead, alive or fictional) whom you would invite to a dinner party.
  20. If tonight was your last night on earth, what would you eat for your last meal?

Forget about the shop talk, forget asking about their past girlfriends/boyfriends or if they want to get married within five minutes or five years.

After a few more dates when you’re both emotionally invested in a relationship, then that’s the time to dive into the deeper topics.

What is the one question that turns you on or off on a first date? Let me know by leaving a comment below!

And if you want to be kept in the loop with my dating articles, advice and tips, subscribe to my blog by clicking on the Follow button below. You know … the Follow button on the lower right hand corner staring at you *smirk*

Smooches xo

Featured image can be found at www.nathanwalker.ca


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