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More Meaningful Phone Conversations with These 25 Questions

June 11, 2020 | by Aleeza Ben Shalom

How to get to know someone from a distance.

Do you have a special ringtone for the person you’re dating? What if you had special questions that could enrich your phone conversations and propel your relationship to the next level. These questions will help you and your date begin to see a future together in fun, thought-provoking ways.

Dive into Dreams

We all have dreams and ambitions. Are yours compatible? Will they allow you to complement and fuel each other or will you be pulling in opposite directions? Dating is the ideal time to understand what is really important to each other before the relationship progresses.

  • If you could move anywhere and still have a liveable wage, where would you like to move and why?
  • What does your ideal Sunday look like?
  • What is one thing on your bucket list?

Changing History

Sneak a peek at his or her priorities. Find out in fun, indirect ways what is deep inside your date’s mind.

  • If you could call yourself when you were fifteen years old for a twenty-minute conversation, what would you tell yourself?
  • If you could go back and hands-down win any argument you've had with anyone, what argument would you choose to win?
  • If you could instantly learn a talent or skill, what would you want to know how to do?

Day to Day

Being present means connecting with someone and letting them into your world, being curious about their life and starting to care about how they experience their daily grind. Take a closer look at your days together and share what you are experiencing.

  • What do you look forward to most in the day?
  • What weird thing stresses you out more than it should?
  • How does your current morning routine compare to your ideal morning?

The Creative Side

Find out how creative and witty each of you is. These questions set you up for lots of laughter.

  • If you could add a new word to the dictionary, what would it be and what would be the definition?
  • If you could change what people say after someone sneezes, what would be the funniest thing for people to say?
  • If you had a handful of modeling clay and whatever you made would become real until you willed it back into clay, what would you make and what would you use it for?

What If?

Let loose and have fun answering these which will showcase your (and your date’s) whimsical side.

  • If you could be the CEO of any company, what company would you choose?
  • If you found out the world was actually a simulation, how would you change how you acted?
  • If you could know the truth behind any one secret or mystery, what would it be?
  • If you could become invisible, but it would mean being permanently invisible, would you do it?


Our favorite places shed light on our unique personalities. It is okay to have opposite preferences here because it presents an opportunity to begin working on compromises to satisfy both of your preferences. For example, if you like crowded, busy places and he prefers quiet, you can take turns choosing venues.

  • Where is your most favorite place on earth?
  • Which do you prefer: a crowded mall or a quiet spot in nature?
  • The perfect dinner date would include __________________?
  • When/where do you feel like you are really in your element?

Quirks and Smirks

Let’s have some fun. Let’s see how daring each of you are.

  • Would you take a weekend job for $20k a year to be a human scarecrow and chase birds from fields?
  • Would you sign up to be a colonist on another planet if it meant you would never be able to return to Earth?
  • Would you want to live in a world where everyone's thoughts appeared as text messages above their heads?
  • Who would you most like to sit next to on a 10-hour flight and why?

From Ring, Ring, Ring to Wedding Ring

These questions might be fun to answer, but make sure you listen as least as much as you speak. When you really know and understand each other, you set a firm foundation from which to build. May you continue to build a relationship that grows over time and materializes into a desirable partnership.

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