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.

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

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?

travel hopes and dreams Matthew Micah Wright / Getty Images


What’s your best quality?

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.

happy people on date Tim Robberts / Getty Images


Where is your happy place?

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!

happy place Arman Zhenikeyev / Getty Images


Who is your biggest influence, and why?

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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Do you believe in Karma?

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.


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

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.


What is your biggest fear?

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.


What are you most proud of?

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.

proud business owner Richard Drury / Getty Images


Are you friends with your exes?

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.

friendly exes AntonioGuillem / Getty Images


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

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.

scared woman Peter Dazeley / Getty Images


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