One of the best ways to get to know someone (and perhaps even fall in love) is through interesting conversation.
While you can’t expect every conversation with someone you just met (or even someone you’ve known for awhile) to be deep or meaningful, having a variety of engaging questions at your disposal is always useful. After all, who doesn’t like talking about themselves?
Here are 10 random questions to ask your friends, family, partner, or date; but don’t just interview them–have real conversations 🙂
1. If you had the complete freedom to live your life any way you would like, how would you choose to spend your day?
By asking this question, you can learn what their true passions are, how they feel about their current life, and what their definition of joy is.
2. What’s your favorite memory from childhood?
This question will help you get a glimpse into their past, which often speaks volumes about who someone is in the present. It can give you insight into how they grew up, what they value, or things they missed out on.
3. If you could go back in time and change something that happened, what would it be and why?
This question could help you understand how easy or difficult it is for them to make peace with the past. Regret is something that weighs heavy on people, so it’s good to know which direction they lean.
4. What is your earliest memory?
This question can be a great way to learn more about their personality or how they view themselves. For some, their first impression of themselves was formed early on in life and tends to stay with them into adulthood. Memory can hint at a person’s fondest dreams or greatest fears. Be prepared for some interesting stories!
5. What is your biggest frustration right now?
This question can give you an insight into what they’re dealing with in the moment, their current state of mind, and how easy or difficult it is for them to talk about things that bother them. Keep in mind that everyone has different ways of coping with stress–some people like to vent, others simply want to forget about it.
6. How have you changed in the last 3 years?
Experience, knowledge, and life lessons all shape the people we become. This question can be a great way to get insight into what they value and how their priorities have shifted over time.
7. What is your greatest fear?
This is a great way to learn what keeps someone up at night, as well as how they process fear. This isn’t necessarily a negative question–it can help you understand their emotional makeup and coping skills.
8. What do you think you’re really bad at?
Everyone has different strengths and weaknesses, but we can all be better at something. This question gives the person an opportunity to help someone else improve their life or simply laugh about a shortcoming.
9. What are you the most grateful for?
There’s nothing more meaningful than gratitude. This question can be a great way to get an insight into how they view the world, what they value, and what they appreciate.
It can help the two of you understand what really matters to them at their core. Is it family? Love? Adventure? Freedom?
10. What do you wish someone had told you when you were younger?
This is a great question to ask your mom, dad, or favorite teacher–but any person can give interesting perspectives about lessons we don’t learn until we’re older. It’s also a good way to get insight into their wisdom and how they’ve grown over the years.
Who are you going to ask some of these questions to?
While these questions are random, they’re also insightful. It will help you get to know them on a deeper level, while also making them reflect inward.
By asking these questions, you may be surprised at what you learn!
