It’s exciting to meet new people and learn about how others are making their way in the world, but it can also be intimidating and downright scary for some people to start a conversation with a stranger with the intent of getting to know them.
We just don’t live in this kind of world anymore: you know, the world where strangers talk to one another. We should make more of an effort to get to know the people around us. You never know what you might learn.
If you are interested in meeting someone new, either for romance or friendship, here are 10 questions you can ask them to help get the ball rolling and get to know them on a deeper level than just asking, “how are you?”
1) If you could have dinner with anyone in the world, whom would it be and why
This is a great question because it opens up a whole other realm of conversation: you could talk about what the person did with their lives, the kind of work they did, the contributions they made, their families, and more.
2) Do you think you’d like to be famous? What would you be famous for?
Okay, this is a two-part question, but it’s a great one to ask people because it opens up the floor for dreaming. People love to dream but are not always comfortable sharing their dreams with other people. This lets them open up and have fun with their answer.
3) Before you call someone, do you take time to think about what you are going to say to them?
The answer to this question will provide interesting insight into the person on the other side of your conversation because it will let you know if they are a planner or fly by the seat of their pants. There’s no right answer here, but it’s fun to know how people roll.
4) What does a perfect day look like to you?
The range of answers you are going to get from this one question is going to be staggering.
You’ll find that people have a really varied opinion of what constitutes “perfect” and even then, they are happy to make lots of adjustments and concessions just to have some version of this day exist in their real lives.
5) What do you have in common with your family?
This is a fun question because it lets you peer into the life of this person and to see how they feel about those they are this life with: if they say good things that they all share in common, it’s likely they have a good relationship. If the focus is on all the bad things they have in common, they might not be as close as they are letting on.
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6) What is the one thing you are the most grateful for in your entire life?
Some people don’t know how to answer this question because it is hard to pick just one thing. Some people might say they are just grateful for life itself, but prompt them to pick something specific, however small it may seem. You’ll get a glimpse into what they think is important.
7) What’s your life story?
So few people ever ask this question that it might be met with confusion: “you mean, my entire life story?” But what a way to spend an afternoon, am I right?
We all have so much to share with one another, but we rarely sit down and get to know everything there is to know about someone in our lives. You can take the conversation on a walk in the park, for drinks, or just hanging out at home. Take your time.
8) If you could find out one thing about your future using a crystal ball, what would it be that you would want to know?
This is tricky, but insightful at the same time. People pretend to want to know what is going to happen, but really when it comes down to it, there are certain things we just don’t want to know about ourselves.
Would you want to know how you die? Probably not.
9) What’s the one thing you wish you had done at this point in your life? And why haven’t you done it yet?
You’ll need to probe them a little bit more with this question. People pretend they are happy with their lives but there is so much that goes undone because of “life.” If someone responds there is nothing they can think of, ask them a follow-up question about what they would like to do next.
10) Who is the person that means the most to you in your life?
A lot of people want to say their Mom in response to this question, but dig a little deeper and ask follow-up questions about who has helped shape them into the person they are today, or who has helped them figure out how they don’t want to act. We often focus on the good, but what about the bad?
Regardless of whether you’ve just met someone at a party or you’ve been married to them for forty years, there is always something left unsaid or unknown about the person standing in front of you. Be brave and ask some bold questions and your conversations will get a whole lot more interested in no time.
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