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Upon meeting a new person, it can be hard to determine their true personality when we go based on what they are telling us on their own behalf. Regardless of whether this person is a new potential friend, a possible romantic partner, or even a candidate for a job, understanding someone’s true intentions is important.

Not only that, but first encounters can be awkward. When you don’t know someone, it can be hard to gauge how to talk to them, or what interests them most. I don’t know about you, but I know that I personally have been in one of those situations where I have just met someone, and quietly sit there, wondering how to break the ice.

Thankfully, that’s where questions like these can really come in as beneficial. Not only do they help you to get to know someone on a much deeper level, quickly, they also help to ease the awkwardness that typically follows when meeting someone new.

1. What makes you happier than anything?

When people discuss what makes them happiest, they shine more than at any other time. By asking this, you are getting a sneak peek into many areas of their personality, and if the connection continues to grow, you will have this to go by in the future.

2. What is your biggest fear?

Fear is one of the strongest driving factors for people. Next to love, it’s likely only second. By asking someone new about their fears, you are understanding one of the deepest parts of themselves.

3. What motivates you?

Motivations vary by person. Some of us are motivated by sheer will, while others are motivated by the people we love most. Finding out what motivates you can truly tune you into the type of person they actually are.

4. If you could take one day to do anything in the world, what would it be?

If we are being real, the vast majority of adults are not living out our dreams. So, rather than just assuming what they do know is what they want to do most, ask them. You might be surprised by what they say in return.

5. Who are your biggest inspirations?

There’s an old saying that goes something along the lines of “the people you surround yourself with are what you will become.” And I believe the same could be said of the people we view as heroes or role models.

6. How would others describe you?

This is one of my favorites because when you ask someone to describe themselves from someone else’s point of view, you can see how truly self-aware they actually are. Additionally, you can view other aspects of their personality, such as humbleness and self-esteem. Above all, you can use it to later compare to how you eventually grow to view them.

7. What do you think your weaknesses are?

A long time ago, I was in a job interview, and the interviewer asked me this question and for a moment, I was bumfuzzled. Usually, in interviews, you are trying to “sell yourself” to them. I blurted out one of my biggest weaknesses without even thinking about it, and she laughed, said “me too,” and gave me the job. This is a great question because it catches people off guard, and it’s most likely that they will give you some real truth in response.

8. If you could travel anywhere, where would you go?

Everyone dreams of travel, even if it’s just a few states away. When you ask someone this question, it’s likely they will respond with a sparkle in their eye as they describe the travel destination of their dreams. When they tell you, ask them why for even more insight.

9. What is your favorite quote?

Everyone loves quotes. If they didn’t, Facebook wouldn’t be filled with meme after meme after meme. Most people will respond with a powerful quote that has pushed them through hard times, which makes this a great question to get to know someone.

10. What are your favorite hobbies?

Not only does this question allow you to get to know someone better, but it also provides a bonding opportunity. It’s likely that somewhere in the midst of their hobbies, the two of you will share at least one in common. If not, you can share talk of what the hobbies are like and learn something new.

11. What do you do to wind down?

Some people will respond with things like “having a few drinks with my close friends,” while others may say something like “golf,” or even “yoga.” Because the answers can vary so much, this is a really personal question and one that provides some deep insights.

12. Who is your favorite person?

Everyone has a favorite person, whether it’s our mom, our partner, our best friend, or our sister. And people’s personalities really shine through the brightest when they are discussing the people they love most.