21 Deep Questions to Ask to Get to Know Someone’s True Personality

How do you get to know someone’s true personality? It would seem weird to ask a relative stranger about their values and beliefs.

Luckily, the following questions are good conversation starters that reveal more than you might think. Read on to find some great deep questions to ask someone to get to know them better.

When thinking of deep questions to ask people to get a conversation started, it can be wise to pick ones that can’t be answered with a yes or no. Those types of questions lead to stilted conversations and awkward pauses.

Instead, pick an interesting subject that will help the other person open up a bit about themselves and their views.

Asking the right questions can stimulate more meaningful and interesting conversations. They can lead to the discovery of common interests and mutual understanding.

It is as well to be cautious about how you ask someone questions. You don’t want them to feel they are being grilled or that you are asking questions that are too revealing. Bear these points in mind and choose questions that gradually help you to get to know the other person.

The most important factor in getting to know someone is actually as much to do with how you listen than what questions you ask them. Give your attention fully to what they say so that you can respond appropriately and begin to develop a deeper bond.

Don’t forget to share something about yourself too. If you force the other person into doing all the talking, they can begin to feel pressured. This can make them feel vulnerable and as if the relationship is one-sided. Sharing something personal, but not too personal, about yourself can help to build trust.

The below list provides a mixture of light-hearted and deep questions to ask someone to get to know them better:

Light questions to ask someone when you first meet:

These questions are light-hearted and will not seem too weird to a potential new acquaintance. However, they can actually reveal a lot about what the other person enjoys, cares for and dreams of.

• Would you rather live in the city, by the sea or in the woods? Why?
• What was your dream job growing up?
• What characteristic do you most admire in others?
• How do you like to spend your free time?
• If you won the lottery, what would you do?
• If you could travel anywhere, where would you go and why?
• What is a skill you’d like to learn and why?

Deeper questions to ask to get to know a person better:

Once you know someone a bit better, you might like to ask some deeper questions. These questions reveal more about a person’s background and fundamental beliefs and values as well as their accomplishments and what drives them in life.

• Which historical figure would you most like to be?
• If you had to choose to live without one of your five senses, which one would you give up?
• If you could take only five items with you to a deserted island, what would they be?
• What is your best childhood memory?
• If you had a chance for a “do-over” in life, what would you do differently?
• If you could witness any event of the past, present, or future, what would it be?
• What do you feel most proud of?
• What teacher in school made the most impact on you and why?

Really deep questions to ask someone once you have started to get to know them:

The last questions are some of the deepest and should be saved for when you know someone reasonably well. Some of them ask the other person to reveal very personal details and become quite vulnerable.

So make sure they are comfortable with the questions and don’t push too hard if they don’t want to answer. If they seem uneasy, switch back to some more light-hearted questions for now.

• What was one of your most defining moments in life?
• What is your ultimate goal in life?
• Who is your biggest hero?
• Tell me about your fears, what are you most afraid of?
• What is the craziest, most outrageous thing you want to achieve?
• What was your most embarrassing moment?

Closing thoughts

These questions are all great conversation starters, but they often reveal more than you think about a person’s values in life. They seem quite casual but can tell us a lot about another person’s personality, desires and values.

Of course, you must consider the situation and the other person’s reaction. Some people do not like to give away too much information about themselves too quickly.

Allow the person to feel comfortable in what they reveal about themselves and dial it back if you suspect they are uneasy.

At the end of the day, there is no point in rushing into a relationship with someone. Asking these questions can help you get started, but remember that the best friendships and relationships take time and commitment to develop.