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Questions for great conversations and relationships

Questions are the greatest way to deepen your understanding not only when it comes to knowledge, but also to building up relationships.

Friendships are powerful because they are cultivated in time, and you have the chance in time to discover the person, learn about his pleasures or weaknesses.

But what about new colleagues or people you meet when you move to a new city?

Or a fling that becomes someone you want to date?

“It doesn’t matter where you are in the organization, you can ask interesting questions that inspire and incite others to think about things they wouldn’t have thought about.” Tim Brown IDEO CEO

Questions become a powerful tool that can trespass even time barriers. They might be hard to come up with on the spot because although you are social and great at subject diversifying, "reading the news kinda person" or a good gossiper, it doesn't mean that you also know how to ask smart questions.

I'll share a list of interesting ones that you can pop up even in a boring meeting, or sprinkle in your Tinder chats or on "date-walks".

And since Covid-19 is still keeping us indoors and less social, we might use that to deepen what we already have and during a dinner with friends there is another type of game, levelled up from Never have I ever... - 100 Questions from The School of Life.

Yes, they have a Love edition too, in case you have that someone over for some wine.

Esther Perel also launched something which keeps selling out and is only available in the states Where Should We Begin — A Game of Stories.

Questions that help you connect with anyone in a more meaningful way

Back in time - childhood

What were you like as a child?

How do you think you've changed over the past few years?

How did you deal with your feelings and emotions growing up?

What moments or events during your childhood shaped who you are now?

What was the first thing you bought with your own money?

Tell me about a day you had that you’ll never forget.

Powerful present

What do you do that causes time to feel different?

What do you enjoy doing regardless of the opinions of other people?

What do you think about most?

What are five things you’re thankful for right now?

What are some of your flaws that you accept and don't want to change?

Friends and foes

Who do you trust? What do you value in a friendship?

What's the nicest thing someone did for you and what did you do nice for someone?

Who or what has changed your life?

What is the one thing that people always misunderstand about you?

What do you personally think of your friend's relationships?

What’s some of the best advice you’ve ever gotten?


If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?

If you could wake up tomorrow having gained one quality or ability, what would it be?

If you could change something in the world, what would it be?

Future gazing

What makes you happy?

What do you want more of in your life?

In 10 years, how would you like to describe your life?

What are the five most important things on your bucket list?

What’s your ideal weekend?

If you could take a year-long paid sabbatical, what would you do?

Is there something you’ve dreamed of doing for a long time? Why haven’t you done it yet?

Fun memories

Describe in 3 words your first kiss/time

Describe in 3 words your worst date

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