If you want to move a friendship past surface level, figure out whether to commit to the person you’re dating, or reconnect with an estranged family member, here’s how to do it:
Ask deep questions!
Deep questions are the opposite of small talk. They help you genuinely get to know someone by understanding their passions, values, and worries.
Thought-provoking questions can also help you feel closer to someone and even increase intimacy in a romantic relationship.
So, what questions should you ask?
Here are my top 10 questions for breaking the ice and creating authentic and meaningful connections.
1) What was your childhood like?
Whether we like it or not, we are shaped by our pasts.
According to Dr. Lucy Maddox, author of “Blueprint: How Our Childhood Makes Us Who We Are,” our childhoods can determine how we show up in relationships and react to stress and challenges.
What’s more, research on childhood resilience has found that children who grew up without a stable child-parent relationship are less likely to develop coping skills. These include the ability to plan and regulate their behavior as adults.
In contrast, if someone grew up with a loving, stable relationship with one or both parents, they are more likely to do well in the face of hardship and diversity.
So, if you want to understand the behaviors and thought patterns of someone, learn about their past.
2) What is your definition of success?
The answer to this question reveals a lot about the person’s beliefs and values.
Answering something like “making lots of money” or “having financial freedom” shows that money is their main driver in life.
Alternatively, if someone answers “starting a business” or “working for myself,” this shows they strongly value freedom and independence.
Of course, the answer to this question can range significantly, as everyone has a different version of success.
For some people, success may be related to health, family, or travel rather than career or money, which is why the question can help you learn much about someone’s values.
Here’s another question that can help you understand what someone values the most…
3) If you knew tomorrow would be your last day on earth, how would you spend it?
Many people say they would spend quality time with all their loved ones. But you can also get some very interesting responses, such as:
- Do all the things I’ve been scared to do
- Let go of all grudges and build bridges with those I have difficulties with
- Say sorry to someone I hurt
What’s interesting about these responses is that they all involve letting go of something to find peace. Because, of course, we all want to rest in peace in the afterlife.
That’s why the answer to this question doesn’t just reveal someone’s values but also what pains and unresolved issues they are holding onto.
As a side note, I also love asking people this question as it gets them to reflect on their current situation and start living like tomorrow will be their last day!
4) What keeps you awake at night?
This is one of my personal favorite questions for getting to know someone on a deeper level.
It is more a metaphorical question than a literal one, as replaying the day’s events is the main thing that keeps people up at night.
What we are really asking someone is what is the one thing in the world they wish they could change the most.
I firmly believe that everyone has a cause they deeply care about, whether it’s world hunger, stray animals, or social injustice.
So, I find this an excellent question for learning what someone’s cause is.
5) What is your biggest fear?
If you want to get closer to someone, invite them to open up and be vulnerable with a question like this.
No matter how courageous or confident we like to appear to the world, we all have worries and fears deep down.
This doesn’t have to be a phobia like a fear of spiders or heights. It could be fear of something happening, like a loved one passing away or a business failing.
For example, my biggest fear is to die with unaccomplished dreams.
6) What past accomplishment are you most proud of?
This question can help you learn a lot about someone’s past, as the answer can open up an interesting conversation if they reveal something you had no idea about.
You ask your uncle this question, and he says, “Touring the world with this band.” From this, you learn he was in quite a successful band in his early twenties but never spoke about it because the band broke up over a big dispute.
Or you ask this question to a colleague who seems dull, and they tell you their biggest accomplishment was running an ultra marathon!
So you see, this question can make you see someone in a whole new light.
7) What makes you feel alive?
This is a fab question for learning about someone’s interests and passions and understanding if they will make a compatible partner or friend.
If the person you’re asking really thinks about their answer, it could open their eyes (and yours) to a passion they have suppressed or ignored.
Here’s an example:
Let’s say in your twenties, you loved to travel and spent several years backpacking in various parts of the world. But before you knew it, you got older, got a stable job, and settled down.
Now, if someone asks you this question, your mind might instantly take you back to your travel days, as this was when you felt most alive.
This may then make you realize that you’ve been so busy with life that you haven’t traveled anywhere in several years. And now you think about it; you haven’t felt very alive lately…
8) If you could do anything you wanted, with unlimited money, time, and resources, what would you do?
This is a deeper way to ask someone, “What is your biggest dream?”
I find this question more effective than if you simply ask someone what their biggest dream is. With that question, they may answer based on what they think is realistically possible.
However, if you frame the question around a hypothetical situation where money, time, and resources are no issue, they are more likely to dream bigger.
So you see, this is a great question for getting into the heart of someone.
It also helps you understand how ambitious someone is, along with this one…
9) What do you want to be remembered for when you die?
Ask someone this question, and you’ll learn what someone sees as their life purpose.
As we all have different purposes, the answer can vary greatly. It might be one specific achievement or a set of values, such as:
- Making a difference to a particular cause through their charitable work
- Starting multiple successful businesses
- Getting their family out of poverty by creating generational wealth
- Being helpful and compassionate to everyone they met
10) If you won the lottery tomorrow, what would you do with the money?
Asking someone this question will give you a good idea of someone’s money habits.
If they answer something like “buy a big house” or “travel the world,” it suggests they are more of a spender. It also shows they may be impulsive and lack money management skills.
However, if they say they would invest the money or put it into a high-interest savings account, it shows they are a saver and, thus, are probably pretty good with money management.
According to the Klontz-Money Script Inventory, everyone has one of four money mindsets:
- Money status – People who associate money with self-worth and are likely to spend too much as a way to show off to their peers.
- Money worship – People who associate money with happiness. These people try to solve their problems through spending money.
- Money vigilance – People who feel concerned about their financial health and associate money with safety. These people tend to avoid spending money unless absolutely necessary.
- Money avoidance – People who believe money is evil or that they don’t deserve it. Because of this, they may sabotage their financial success by giving away any money they get or making excessively large donations.
With this in mind, asking someone this question is a great indirect (and sneaky) way to figure out someone’s money mindset.
Speaking from personal experience, if you start to sprinkle these questions into your conversations with your loved ones, you will quickly feel a stronger connection with them.
And if you’re stuck in the small talk trap with colleagues and want to break free from the mundane “how was your day?” question, ask one of these instead.
People are often taken aback when you throw a thought-provoking question at them. But after a moment, they start to think about it, and it opens up a beautiful and deep discussion.
And isn’t that what we all want more of in life – authentic connections?