Below you’ll find icebreakers and deeper questions to help you have a great conversation and deepen your relationship for a range of scenarios.

These questions have been pulled from the Holstee Reflection Cards. Learn more at: holstee.com/cards


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Questions to ask on a date.

Questions to ask on a date

Sometimes it can be hard to find just the right question. On a first date it can be hard to know where to start, and on your 100th date it can be hard to ask something you haven't yet. Here are a few questions to help jumpstart a meaningful conversation.

Icebreakers to ask on a date.

  • What is the kindest thing a stranger has ever done for you?
  • What is one dish you parents or grandparents make that you wish you could make?
  • Do you make decisions more with your head or heart?

Deep questions to ask on a date.

  • If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?
  • What message would you put on a billboard that thousands of people would see every day?
  • How do you want to be remembered?

Questions to ask on a road trip.

Good conversation on a road trip.

Road trips are the quintessential moment to learn about your co-pilot. Use these questions to pull out some really fun stories and get a better sense of appreciation and understanding of your companion.

Icebreakers to ask on a road trip

  • Has anything ever happened to you that you could not, and cannot, explain?
  • If you could have front row seats to any concert, ever, which would you choose?
  • What is the worst place you have ever tried to sleep?

Deep questions to ask on a road trip

  • How will / did you know you are in love?
  • If you could change anything about the way you were raised, what would it be?
  • What is the closest you have ever come to dying?

Questions to ask at a group dinner.

Good dinner table conversation

Dinner tables are the perfect place to have a meaningful conversations. Connecting over food has a long rich history and is a part of many traditions and cultures. Sometimes all you need to take the dinner conversation to the next level is the right question. Here are a few to get you started.

Icebreakers to ask at a group dinner.

  • Your house and everything you own, catches fire. All pets and people are safe, but you can save one single item. What do you choose?
  • What is one thing that doesn’t cost anything, occurs naturally, and always make you smile?
  • If you could spend a day as any animal, which would you choose?

Deep questions to ask at a group dinner.

  • What makes you weird?
  • If there is an afterlife or reincarnation, what one memory from this life would you bring with you?
  • What is the biggest risk you've taken? If you had another chance, what would you do differently

Questions to ask at the campfire.

Good questions and conversation to have at a campfire.

The fire is crackling, the the air is cool, you are with some incredible people, a perfect moment to deepen your relationship at a memorable moment. Here are a few questions to warm up:

Icebreakers to ask at the campfire.

  • Do you have any rituals or home remedies for feeling better when you get sick?
  • Are all emotions beautiful?
  • When you think about childhood adventures, what memory comes to mind?

Deep questions to ask at the campfire.

  • Do you believe you have a soul? If so, where in your body does it live?
  • What are you holding onto that you need to let go of?
  • What is the biggest risk you've taken? If you had another chance, what would you do differently

These questions are selection from our research of thousands of questions to build the perfect deck of reflection question cards. We hope they were helpful in sparking memorable moments for you and your loved ones.

Want more questions? Pick up a deck of Holstee Reflection Question Cards here.

Holstee Reflection Question Cards

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