Ask These 12 Questions to Learn About a Person

See someone from all angles, not just the public ones

This isn’t your boring game of 20 questions.

These are powerful, carefully selected, and field-tested questions that are guaranteed to help you gain insight.

Ask these to someone you want to know intimately — whether that’s your partner of 10 years or a month.

Getting Interesting Answers

Before we get into these questions, let me give you a quick tip, okay?

Sometimes people answer short by nature or because they’re not sure how much to elaborate. As someone who was a journalism major, I used to try to find “micro questions” to get people to expand. Wrong.

These three phrases will turn those quick responses into well-thought-out answers:

• “Tell me more”
• “Say more about that”
• *Silence* (people get uncomfortable and tend to fill the space)

We’re about to get deep and a little in the feels. This could bring up some negative emotions. If anyone is uncomfortable with a question, it’s their right to reject answering, so avoid prying.

Alright, you ready to learn a lot about your person?

#1 What’s The One Thing You’d Change About Yourself?

This is one of the oldest questions I’ve asked people. Some respond with something about their looks. Some respond with a personality characteristic. Others give a laundry list of both.

This question helps you learn what the person is self-conscious about. It could help you navigate their sensitivities.

For example, if you know a person isn’t proud of their height, you can avoid putting them in situations where that’s triggered. And if it is triggered, you’ll know and can respond appropriately rather than wondering why they’re upset all of the sudden.

#2 What’s your Biggest Fear In Life?

Similar to the question above, this one allows you to take a deep dive into their most personally held beliefs.

Why is this important? It can help us gain insight into what they’re sensitive to. This can inform how we act and what we say when these issues come up.

One of my exes was really sensitive about his age. (Granted, he did lie to me about it for about 7 months.) Still, this informed my decision not to make jokes about his age and to avoid any comments that would trigger his insecurity of not being where he thought he should be in life.

#3 What’s One of The Biggest Misconceptions About You?

I love this one so much. How often do people think wrong things about you? Probably all the time. Most of them, we’ll never know. But chances are, we’ve heard a few common ones over the years.

Maybe people assume you’re a mean person because you have a serious job. Or you talk about serious issues, so people think you’re humorless. There are so many judgments that are made each day. Which ones does your partner get?

This question can help reveal assumptions you’ve made about them. It might also help you understand the way they operate in the world.

For people who don’t know me, one of the misconceptions is that I’m rude because I don’t talk much. In reality, I’m super introverted, shy, and have social anxiety. This is helpful for a partner to know because they’ll understand it’s not that I hate the people at the party. It’s that I hate the party, and I’m probably fending off an anxiety attack.

Asking questions can help us know where someone is coming from when they’re put in front of people they don’t know.

#4 If You Could Teach Everyone in the World One Thing, What Would That One Thing Be?

This is a really hard question to answer. Your person might have several answers for this one, and all would be telling.

What someone wants to change about the world could speak deeply to who they are and what they’ve been through in life. On the less deep end, it also makes you aware of some really big pet peeves they have.

Not everyone is a secret philosopher. But if the one thing they’d change about the world is “how to use the passing lane for passing and the slow lane for taking your sweet ass time” — well, maybe they’re not so deep. (They sure are right though).

#5 What Are You Most Ashamed Of?

This is a question that should probably be reserved for when you know someone better. If you’re on a first date and ask this, it’s likely going to make the person uncomfortable and really, it’s not a therapy session.

Still, though, aren’t you interested to know?

The answer could reveal something that happened in the person’s past that helped shape who they are today. It could lead to new ways of understanding them.

This is another question that could show their ability for self-reflection too. If they’re ashamed of how they treated someone, you see they have the ability to identify and hopefully learn from their mistakes.

#6 What Are Your Biggest Pet Peeves?

It’s one of the more light-hearted questions on the list.

Learning about someone’s pet peeves lets you know the things you might consider avoiding.

I don’t like it when people talk non-stop. Knowing this is helpful because then I don’t have to have the awkward conversation of “hey, do you mind putting more space between your words and thoughts” (actually happened, I felt bad).

#7 What Do You Think About [Insert Issue Here]?

I’ll say it. The advice of “don’t bring politics up on a first date” is stupid.

I’m convinced the only people who give this advice are the ones who don’t want to be outed for their idiot opinions.

If you’re looking for someone long-term (or even short-term), you probably want them to agree on the main things you do. To put it plainly, why would you want to be stuck with a bigot?

I was with a Trump supporter, and it was horrible. All we did was argue about basic human rights. When I’d bring up logical fact, I was met with some crap about Bill Gates, pizzagate, or the gates to America’s biggest cult.

That’s not a relationship, that’s a 2-year debate.

The question could be about anything you think is important: Human rights, racism, feminism, politics, gender rights, animal rights, etc.

Don’t be afraid to ask the hard things upfront. It could prevent you from dating someone who makes you want to hire a bodyguard for your uterus or bash your head against Trump’s tiny wall.

#8 If You Became a Parent, What Would You Do Differently Than Yours?

Even if the person doesn’t want kids, they probably have an idea of a few things they’d do differently than their parents.

This question can be a less intimidating way to say, “tell me about your childhood traumas.”

The things your person would want to do differently could point to how their childhood was growing up.

According to the CDC, 61% of adults have had at least one adverse childhood experience (ACE). ACE could include exposure to:

• Family violence
• Divorce or separation
• Substance abuse, including alcohol problems
• Criminal behavior
• Abuse- physical, emotional, sexual
• Witnessing another’s abuse
• Poverty

This is something that can help you understand part of what made the person into who they are today. There’s been a lot of research into how ACEs change who we are as people. They’re associated with a higher risk for anxiety, depression, substance use issues, and physical health problems like asthma, cancer, and diabetes.

Learning about an ex’s heavily abusive father gave me a better appreciation for his battle with substance issues. Of course, nobody’s past is an excuse for how they treat you. But it can give you hints on why a situation is occurring or how a personality trait came to be.

#9 Out The Criticism You’ve Received, What Do You Disagree With? What Do You Agree With?

This is a good question to ask the person you’re seeing because it shows their awareness about how people perceive them.

For example, if someone constantly gets the criticism they’re rude and they just don’t see it, there’s a good chance they’re rude. This could be something to look out for.

But the question could reveal a high level of self-awareness too. Someone may reveal a characteristic about themselves that they’re working on.

For people who are honest, there’s a chance of increasing vulnerability and bonding. It’s hard to admit when people are right about something negative about you. Opening up about your downfalls could help you understand each other and bring you closer.

#10 What Was the Lowest Point in Your Life?

Although it’s another question you probably wouldn’t ask on a first date, it’s one that could lead to great conversation and insight.

You might learn about someone’s darkest moments. This can help humanize them and let you see them from all angles, not just the ones they present outwardly.

Of course, if someone rejects to share because it’s too personal, we should always respect that.

#11 When’s the Last Time You Cried?

Asking someone the last time they cried can open the doorway to some interesting, deep conversations.

It can let you know how emotional a person is in general. Are they one to cry at a Hallmark movie commercial? Or do they prefer keeping their feelings inside?

Ask follow-up questions about what they cried about. Learn about the things that tug on their heartstrings the most.

#12 Tell Me A Secret You’ve Never Told Anyone.

This one could go a lot of different ways. It could be serious, fun, dirty — whatever the mood is right for.

If the person asks, you can give them a category. But I think leaving it open-ended always leads to the most interesting result.

I wish I could tell you the secrets I’ve learned by asking this. But well, they’re secrets.

Get Asking

The same questions lead to the same conversations. To get deeper and learn more about someone, use the questions on this list.

Remember that some may be too personal and it’s everyone’s right to refuse to answer. If you notice answers are short, use silence or phrases like “say more” to coax more out.

Above all, keep curiosity at the forefront by asking things you’re genuinely interested to know.