As someone fascinated by intimacy, I ask a lot of prying questions.

Sometimes this results in meaningful, relationship-building conversations. Other times, I catapult myself into awkward, uncomfortable encounters that bring me further from the person I was trying to know, rather than closer.

After reflecting on some of the best and worst conversations I’ve had with family, friends and strangers – I compiled a list of 50 questions to ask someone you really want to know.

Some are inspired by personal experience with friends and partners, others are stolen from articles I read long ago at 3AM on Facebook (apologies for the lack of sources). Some come from Archetypal Nature and similar personality type philosophies, others are based on academic research into human psychology and sexuality I conducted during my degree. All of them are (subjectively) proven to result in insightful, intimacy-building life chats.

Categorised into five core topics; these questions have sparked some of the best conversations, friendships and relationships I’ve ever had. They’re the perfect balance of disarmingly direct, yet not so revealing that they send people running. I’ve roughly organised the topics – identity, motivation, friends, family and relationships – from least to most intimate (re: risky).

I’d love to hear how they work for you in your encounters with partners, friends and random people on public transit. Without further ado…

Here are my 50 questions to ask if you really want to know someone.

Questions about Identity + Self

1. What do you love to do when no one else is around?
2. Do you prefer to spend time alone or with others? Why?
3. What was your favourite book or TV show growing up and why did you love it?
4. What’s one thing you’ve always wanted to do, but were too afraid to do it?
5. What are you most afraid of? Why?
6. What’s “your crazy”?
7. Given the choice between climbing a mountain and reading a book, which would you choose and why?
8. What’s your most prized possession? What does it mean to you?
9. How do you feel about inebriation? What’s your relationship to alcohol/drugs?
10. What’s the coolest thing you’ve ever done? Why did you like it so much?

Questions about Passion + Motivation

1. What career would you want to pursue if money was no object?
2. What activity leaves you feeling more energized whenever you do it?
3. What was your degree? Did you choose it? What lesson resonated most with you?
4. What are you loving most about life right now?
5. Is your current job your dream job? Why do you do it?
6. Do you actively set goals? How often do you feel you achieve them?
7. What is the number one priority in your life right now?
8. How important is wealth to you? Is money something you think about often?
9. Are you motivated by service? Do you genuinely enjoy helping others?
10. Why did you choose the industry you’re in? Was it what you thought?

Questions about Friends

1. Who is your best friend? What do you love most about them?
2. Do you prefer to have a few great friends or many good friends? Why?
3. Who is your oldest standing friend? What do they provide in your life?
4. What’s your favourite thing to do with your friends?
5. Are you actively seeking new friendships? Why / why not?
6. Are you more interested in doing things FOR other people, or WITH other people?
7. Should friends ever lend other friends money? Why / why not?
8. Who was your childhood friend? Are you still in touch? Why / why not?
9. Do you hate/dislike any of your friends? Why do you keep them around?
10. What trait does your best friend have that you wish you could have (but don’t)?

Questions about Family

1. How do you feel your parents’ relationship affected your views on relationships?
2. How close are you with your sibling(s)? Why do you think that is?
3. How do you feel being an only child affected your outlook on relationships?
4. Did you move much growing up or stay in one place? How do you think that affected you?
5. Do you think you’ll ever have children? How important is that to you?
6. What do you think about marriage? What does “married” mean to you?
7. Were you closer to your mother or father? Why?
8. Was religion a big part of your upbringing? How do you feel about it now?
9. Do you spend much time with your extended family? What do you do together?
10. What’s your opinion of holiday seasons? Do you look forward to them or dread them?

Questions about Relationships + Sexuality

1. What made you fall in love with your last partner?
2. Are you more of a serial monogamist or a lone wolf?
3. What’s your number one deal-breaker for a relationship?
4. How do you feel about monogamy? Do you think it’s natural? Do you value it?
5. Have you ever cheated? Why did you do it? Do you feel bad about it?
6. Did you speak about sex with your parents much growing up?
7. How do you feel about nude beaches?
8. Do you prefer to be in control or surrender control in bed? Why?
9. What’s your favourite thing about having sex?
10. What’s your kink? Why do you think you’re drawn to it?

Over to You…

Which ones inspired you to respond? Which ones made you squirm?

What questions would you add to the list?

I’d love to hear your thoughts in the comments below or via email.