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Questions That Help You Get to Know Someone

By Staff Writer
Share to PinterestQuestions That Help You Get to Know Someone
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Meeting someone for the first time can be exciting yet daunting. How quickly you become comfortable in their presence depends on your initial communication, the surroundings, and whether or not you feel a connection. Asking smart, detailed questions from the get-go is key to understanding the other person and finding out if there is a friendship or romantic relationship in the cards.

01

If money wasn't a factor, what would you be doing with your life right now?

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Like it or not, money matters, and finances often have a big impact on what people can and cannot do, but everyone has dreams of their future if money wasn't an issue. Maybe they have a dream career that's on hold or want to travel the world. How do their imaginative plans lines up with your outlook on life?

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02

What’s your best quality?

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Everyone has strengths and weaknesses. Think about the qualities that matter most to you, whether it's honesty, positivity, loyalty, work ethic, or any of the dozens of other possibilities. Ask your new acquaintance to share their perspective on their best qualities. They don't need to perfectly align with yours, but this is a great question to gain more insight into how they see themselves.

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03

Where is your happy place?

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Light-hearted topics are great for early conversations when you're still getting to know someone. Their answer can give you an idea of what makes them happy and what they like to do in their spare time. Plus, you can see if you have a happy place in common. The answer also opens up tons of follow-up questions if you feel like the conversation is starting to lag!

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04

Who is your biggest influence, and why?

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Your potential friend's answer to this question can reveal more than just a favorite celebrity or family member. If their mother or father makes the cut, you can assume family is important. If the answer is someone famous, you can infer many values from what you know of their influencer. Be sure to ask follow-up questions, though, as the reasons for a connection to a specific person might surprise you.

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05

Do you believe in Karma?

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Regardless of whether or not you accept the idea that the good and bad things we do affect the good and bad things that happen to us, this is a great question to open up a conversation about responsibility and the universe. If kindness and compassion are important to you, and you want people in your life who feel the same way, introduce a discussion on the consequences of our actions. Whether they believe the universe, the law, or nothing at all governs their actions and rewards, it's bound to be an interesting chat.

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06

Which TV or movie character do you identify with, and why?

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It's nice to break the ice with a fun pop culture question. Getting to know someone involves asking about their favorite things, and everyone loves to dish on their favorite film or TV show. Whether this question turns into a discussion on the latest binge-worthy shows or something deeper, pop culture often opens up interesting doors into lengthy conversations.

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07

What is your biggest fear?

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It's normal to have semi-superficial conversations when you first meet someone, but eventually, you have to dive into some deeper topics. Talking about what you're both afraid of can shed light on similarities and vulnerabilities and might even open up into childhood experiences. Questions like this are also an opportunity to gauge how willing the person is to share their deepest thoughts. If they're hesitant, it could be a sign that it's too soon for such topics — or maybe sharing your own experience first can help.

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08

What are you most proud of?

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You can learn a lot about a person by asking about their proudest moments. Their answer will reveal what they value and how much self-confidence they have. If someone can openly share their accomplishments with pride but also humility, this can indicate some great personalit traits. If they use the opportunity to brag about how amazing they are for minutes on end, you may be dealing with an inflated ego.

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09

Are you friends with your exes?

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Some people have strong feelings about staying friendly after the end of a relationship. If your meeting is with a prospective partner, asking this question upfront will give you insight into their thoughts on the matter, and also clear the air about future messages from former significant others. Even if you have different outlooks on this matter, you can discuss your thoughts and respect each other's opinions.

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10

What was the scariest moment of your life, and how did you handle it?

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An insightful answer to this question can highlight a person's propensity for digging into their problems and dealing with them head on. It might also indicate someone who is open to self-improvement, which is often a positive thing. Of course, just because someone is not ready to talk about a terrifying moment in their life doesn't mean they aren't at a different point in their journey. The goal of this and the other questions is to learn more about a new person, not to form judgments based on a few conversations.

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11

What is your favorite way to spend a weekend?

Share to PinterestA dad helps his little girl go skateboarding, holding her waist for support.
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The way we spend our free time says a lot about us. You learn a lot about a person from whether they like windsurfing and skydiving or quietly reading a book by the fireplace. This is also a really good way to find out what the two of you can do together if you want to hook up outside of work or school.

A lot of people also enjoy talking about their pastimes, and you can watch them light up as they start telling you about their weekends hiking in the woods or the boat they've been building in the garage.

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12

What is the most important lesson you've learned in life so far?

Share to PinterestClose up of a college student sitting in a park and writing in her notebook.
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Life teaches a lot of lessons; some are easier than others, and some stand out more than others. A question like this is good for spotting red flags, such as when a person's main life lesson is "don't trust people," and for finding hidden personality gems, like when they tell you they've learned a sense of humor is more important than a full tank of gas.

You might also learn something by asking this question. "Find a good place for your car keys," "get a haircut before a job interview," and "take good care of your knees, your back, and your credit rating" are all excellent advice, and you can learn a lot from people who'll tell you how they learned it.

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13

What is the one thing you would change about yourself?

Share to PinterestYoung pretty woman checking herself in the mirror in modern bathroom.
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It's a very rare person who's 100% happy with every detail about themselves, and knowing what a person would change if they could tells you about their priorities. Someone who mentions a physical flaw, for example, could be fishing for a compliment, or they could genuinely be unhappy with something about their body.

If they mention a life regret, such as never having children or not sticking to their piano lessons, you might be talking to someone with a lot of self-awareness. If the person talks about something they'd like to change soon, like losing weight or finishing a degree, you have a decent entry point for further conversation about their life goals.

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14

What is your favorite way to relax and unwind after a long day?

Share to PinterestYoung man with hands behind head, relaxing on sofa and listening to music with headphones at home.
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This is similar to asking what your friend likes to do on weekends, but the shorter time constraint you get with an afternoon instead of a whole weekend might bring a person's private life into sharper focus. A person who just likes to unwind in front of the TV, for instance, probably has a different approach to leisure than a home cook or someone who rushes home from the office to get into the workshop and make something on the bench.

This line of talk can even give you some ideas for your own after-work free time. If the person you're talking with is over the moon about their Beatles tribute band, you've almost automatically got a follow-up question about where they play and whether you should catch a show sometime.

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15

What is a goal you are currently working towards?

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Knowing where somebody is going is a good way to know where they're at right now. Is the person you're chatting with on their way to a law degree? A trades apprenticeship? A gap year in Europe? Hearing how someone is working toward bigger and better things is not only interesting, it's as informative as learning from an older person how they're preparing for retirement and what they want to do when it gets to be that time.

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16

What is the best advice you've ever received?

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People tend to remember the important things, and learning what advice a person values enough to remember tells you what's important to them. This could be a big thing or a small thing, from "don't go to school til you know what you want to do" to "always call ahead."

You can also learn more about a person by asking who gave them the advice. They could cherish advice from their father, a teacher, a mentor, or a totally random stranger they met at a bus stop one day.

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17

What is your favorite thing about your job?

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What do you like best about your job, and what do you think that says about you? A lot of people are defined by their work, and what they like best about their job is a big window into their personality.

Don't be shy about asking follow-up questions. Do they like the shift they have? Their coworkers? Are they working toward a promotion? People will tell you a lot about themselves while they're telling you what they do for a living.

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18

What is the one thing you cannot live without?

Share to Pinterestwoman enjoying cappuccino in a cafe
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The most important thing in the world to you is, well, important. People will give you a wild range of answers here. Some serious people will tell you it's their parents or their kids they can't live without, while less serious folks might note the essentialness of vanilla lattes. Best of all, you can let your new friend have fun answering this question.

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19

What is something you have always wanted to try but haven't yet?

Share to PinterestYoung man bungee jumping over river.
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Ambition is more than just the job somebody wants or the places they've always dreamed of going. It's also revealing to find out what somebody has always wanted to try but hasn't gotten around to yet. Is it something adventurous, like skydiving or climbing a mountain, or is it something more humble, like trying sushi or swimming in the ocean?

Depending on what they say, you might even suggest trying it together—it's hard for a person to say no when they've already told you what they most want to try.

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20

Are you a morning person or a night owl?

Share to PinterestYoung woman is waking up and looking at her smart phone.
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The hours we keep are a real distinction among people. Some of us can hardly wait to spring out of bed in the morning and get a head start on the day. Others start slow and keep coal in the boiler all night long. This isn't just a way to get to know someone better; it can also be a helpful hint for when you should text or call and whether they're more likely to meet up with you for a morning jog or a late-night concert.

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21

Do you have any siblings? If so, tell me about them.

Share to PinterestAngry little kids fighting over a remote control while watching TV on sofa at home.
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Your family is arguably the first thing that defines you, and how you talk about family members says a great deal about what you've been up to since you were a kid. Ask about siblings, and  extended family members, too, to learn a lot about a person you've just met.

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22

Are you more of an optimist or a pessimist?

Share to PinterestClose up sparkling in the evening glow and the moon
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What's your basic outlook on life? That glass over there, is it half-empty or half-full? Whether a person is upbeat and looking on the bright side or downbeat and a bit cooler than that can tell you how well you're likely to get along with your new friend and whether they'll get along with you.

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