7 Questions To Ask Someone To Find Out More About Them

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Unless you're the type of person who's truly comfortable in your own skin, revealing your true personality to others can take some time. But according to experts, asking the right questions will help you get there faster. Whether you're on a first date or taking a new co-worker out for lunch, there are some questions you can ask to help bring out their personality.

"Many of us have learned very early on how we are supposed to or 'should' behave, which means we're scared to be fully our authentic self," licensed psychologist Sue Sexton, tells Bustle. "In order to prevent further rejection or judgment of who we are, we take on roles and role playing, in order to play it safe."

It's why some people have a hard time letting their personality shine when they meet new people. They don't want their true selves to be rejected. So instead, they go into their shell.

But you can help someone out of it by connecting with them. Think big talk over small talk, William Haynes, founder of Friendship Hacks tells Bustle. "Try to find unique talking points to create memorable conversations," he says. "This means thinking outside of the box and avoiding those 'boring' questions and topics. Asking questions they may not expect to hear, but that still help find similarities."

So here are some interesting questions you can ask someone to help bring out their personality, according to experts.


"What Is One Of The Coolest Experiences You've Had?"

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When you're trying to bring out someone's personality, it's important to ask questions that will allow them to do so. According to Sexton, asking open ended questions like what their coolest experience was will give them the opportunity to share a story. Are they dynamic? Do like to embellish? Or do they stick to the facts? You can see their personality shine through the type of storyteller they are.


"What's Your Relationship With Your Family Like?"

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"The way a person feels about and talks about their family will show you a great deal about their personality, and who they really are," relationship expert and author April Masini, tells Bustle. For instance, some people with poor relationships with their family may act with outrage when asked. Others may light up and happily share stories. "These expressions about family can help you figure out who it is you’re dealing with," she says.


"What Do You Think About Ghosts?"

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A little silly and fun, this question can reveal if the person you're talking to is spiritual or openminded. "You'll learn a lot about whether they have awakened to a larger reality and you might hear really cool stories, which will help you open up more," Sexton says.


"If You Had A Chance To Start All Over Again, Would You Do Things Differently?"

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Fun questions are great for breaking the ice. But as you keep talking, the more thought-provoking questions can help bring out another side of someone's personality. This may even be the side of them that you connect with. "This question will make the person you're talking to stop and think about whether they have any regrets about important life-changing decisions they made up to now," relationship expert and spiritual counselor Davida Rappaport, tells Bustle. It can even give both you and them insight into their decision-making process, and what their joy and regrets are.


"If Your Friends Were Here, What Would They Tell Me About You?"

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People tend to have one or two fun stories that involve their friends. According to Sexton, posing the question this way will give you insight into how the person sees themselves. Are they self-deprecating or do they have good self-esteem? If you're looking to help someone open up, getting them to talk about their friends can be your way in.


"What's Your Dirty Little Secret?"

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If you both feel comfortable in where the conversation is headed, try asking this question. "This will disclose to you whether they are able to talk about tough stuff or brush it off and play it cool," Sexton says. While the content of their answer can be interesting, pay more attention to how they answer the question. Do they shy away or close themselves off? If so, they may have a more serious personality. If they answer in a cheeky way, they don't take things too seriously and can roll with things easily.


"What Happened With Your Last Relationship?"

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If you're dating someone new, asking them about their last relationship can be awkward. But according to Sexton, it can reveal a lot about how they see themselves. For instance, do they see themselves as a victim or are they mature enough to take accountability for their actions? So pay attention to how they answer the question. Because as Sexton says, "They will repeat this pattern with you in time."

Not very many people can easily show their personality right off the bat. So it's not a bad idea to give people a chance to reveal themselves to you. If you ask the right open-ended questions, you will give them the opportunity to let their personality shine.