Good conversation takes effort and planning. Friendships do too. So, in many failures and a few successes, I found that asking people thought-provoking questions really helps. It doesn’t matter if they answer wrong, encourage them to just open themselves to you so you can just see the basic thought-process they go through to get there. Tell them: Interpret widely, answer specifically.
I always change my mind about these questions. And I try not to plan my answers, so I can be in the same boat of figuring my thoughts out as the person I’m asking is.
In varying levels of intensity…
- What is your greatest fear?
- How do you overcome it?
- What is your greatest hope?
- What trait do you admire/value in other people?
- What do you notice first about a person you are getting to know?
- If you had a social resume, and were forced to brag about yourself, what would you say is your greatest personality/character trait? Or, what would you aspire to have it one day be?
- Where did you come from? (A sort of what-made-you-who-you-are-question). A couple big moments or a small quiet process?
- Who is someone who most affected your life or who you are?
- What is your perfect day? Ever.
- What is your life goal?
- What do you think about in your "”quiet”/”greatest” moments? Is there a general theme at least?
- What is your favorite form of art?
- What is something you’ve always wanted to do?
- What would you spend $1 million on? No saving or investing.
- What super power would you want?
- Are you a beach, country, or city person? Or other?
- If you knew you could try anything and not fail, what would you do?
- Favorite childhood memory?
- Life motto?
- What kind of people do you like? Describe your best friend in as much detail as you can.
- In 5 years, what kind of person will you be?
- What’s your major? Why did you choose it? What do you want to do with it?
- What is your language of love?
- words of affirmation
- quality time
- receiving gifts
- acts of service
- physical touch
- If you could have a wish granted, what would it be?
- What’s your favorite season? Why?
- If you could give the world one piece of advice, what would it be?
- What’s your idea of romance? Is it a feeling or an action?
- Have you been in love?
- Do you daydream a lot? About what?
- Favorite books, movies, songs, artists, etc.
- Six flags or camping?
- A week on a dream vacation with your 3 best friends or 10 minutes on the moon by yourself?
- You have 24 hours to live… What do you do? Famous last words?
- You have a month to live… What do you do?
- What makes you angry?
- What makes you happy?
- What makes you sad?
- What is your favorite/most beautiful doctrine?
- Are you a curious person? Do you ever have questions that leave you pondering for long periods of time? Do you have an example?
- Is there a driving question in your life?
- What is happiness to you? What brings it, but also what is it?
- If you were trapped on an island what one thing would you bring? (Not a tool to get you off.)
- If your house were burning down, what one item would you save?
- What is something you’ve always wanted to do?
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