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Cheeky questions: An enjoyable way to get to know each other better

Try this "game" sometime. You find a partner and ask that person any question you like. The deal is that the other person either answers honestly or declines to answer. If she or he answers, then that person can ask you a question, as before. If she or he declines to answer, you get the chance to ask that person another question, and so on.

It is surprisingly effective and very interesting. You both learn a lot. Most people seem to find asking questions much more difficult than answering them.

This will work best with someone you already have a good relationship with. It does have the power to make good relationships better!

This is not an original idea, but I do not know it's source.

Safety first

Some people have raised legitimate concerns about the safety of the "game". Here are some things you can do to create safety.

The most important thing is to play "cheeky questions" with positive and caring intent. If you do this you will: -

Not use it flippantly or while drunk or drinking.
Ask easy and not too searching questions first.
Listen hard to the answers
Remember the purpose of the game is to get to know each other better
Have an agreement about confidentiality and not gossiping before you start
Ask constructive questions that invite new thinking
Remind each other that it is Ok and perfectly acceptable not to answer a question.
And most importantly, you will be honest. When you are honest this builds mutual trust.

Here are some possible questions.

What good things have happened lately?
What is your happiest memory?
Which subject did you like best at school and why?
What do you like most about your life?
What do you like most about yourself?
What are your greatest strengths?
If you had three wishes for your world, what would you do with them?
What is your highest dream for you?
What do you believe?
Why do people love you?

My wife and I shared a long car journey a few years ago and whiled it away by playing the game. Time flew, it was most enjoyable, we learned new things about ourselves and each other. We had then been married 39 years.


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Phone +44 (0)1707886553, or +44(0)7879861525 email or Skype nickheap

Using these materials
I am entirely happy for you to use or draw on any these materials in any way you think will be helpful. I am keen to have my work, and the work of the people I have learned from, used.  


The language on this site is correct UK English throughout. There are differences in spelling and meaning between UK and US English. The context should make the material understandable in the US.

Further Information

There are free articles, exercises, designs, book references and links to other sources about many aspects of personal, team, management and organisation development on this website. I will add other resources as I learn what you want.

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