There’s a reason deep, meaningful talks can have lasting effects on your relationships. We asked two experts how to go about starting those kinds of conversations.
You may think you know someone, but do you, really?
Whether you’ve known them a day or a decade, there’s something about a profound conversation that can help you see people in a whole new light and, hopefully, strengthen your bond.
If you feel intimidated about jumping into the deep end of dialogue, you’re not alone. So we rounded up 5 examples and 45 questions to help you get started.
Deep connections are based on curiosity and vulnerability, and an imperfect, real exploration, says Jackie Tassiello, a therapist in the greater New York City area.
“The safety of deep relationships is the foundation for so many healing benefits,” she adds. “Some 
What types of questions are best to get to know someone deeply?
You may have seen the viral “36 questions to fall in love” experiment on YouTube.
The original research behind this comes from a series of experiments by psychologist Arthur Aron in the 1990s. He was able to measure how intimacy forms between two strangers in just 45 minutes with a series of deeper and deeper questions.
It works for people in existing relationships, too.
In his book “Eight Dates: Essential Conversations for a Lifetime of Love,” Dr. John Gottman indicates that 4 decades of research shows that in healthy relationships, people make time to be curious and get to know one another.
Kimberly Panganiban, a licensed marriage and family therapist in San Diego, California says, “In order to do this, try to ask open-ended questions. These could be past-, present-, or future-oriented.”
“The goal is to strike a conversation in which you both learn new things about one another and, therefore, feel more connected. Questions that generate discussion about emotions can bring the deepest connection,” adds Panganiban.
Types of questions
Some helpful types of questions may include:
- Open-ended: What’s one movie that made you tear up and why?
- Past: What’s the most memorable dream you’ve ever had?
- Present: What’s the most important quality to you in a friend, right now?
- Future: What’s one quality you hope to change about yourself in the future?
- Needs-oriented: How can I best support your needs right now?
As humans, we are all wired for connection. It’s necessary for our survival and it supports our mental health in many ways, says Panganiban.
“Connection helps us to feel secure in life and about ourselves, which allows us to engage more with the world,” she explains.
“When our basic need of attachment is met, it leaves us open to pursuing other interests, goals, and adventures. We feel a sense of comfort and safety, knowing we have people that we can count on and that love us,” she adds.
A list of questions at the ready can help take some of the pressure off.
(In)frequently asked questions
- What’s a quality you still want to have at age 90?
- What book has influenced you the most?
- What’s your #1 goal right now?
- What’s your quirkiest habit?
- What do you like the most about being “you”?
- What’s one fear you want to master?
- Who’s your role model, dead or alive?
- What was your favorite novel as a kid?
- What’s a quote that inspires you?
- What’s your greatest achievement so far?
- What subject did you look forward to in school?
- Are your priorities different from what they were 10 years ago?
- Has your character been shaped by anyone?
- What’s your favorite memory of helping a stranger?
- What’s the earliest thing you remember as a child?
- Have you had any recurring nightmares?
- What’s a recent lesson your parents/caregivers taught you?
- If you had a time machine, what year would you travel to?
- If you had a free hour, how would you spend it?
- In all of history, who would you spend an afternoon with?
- If you could travel anywhere in the world for dinner, where would it be?
- What animal would you want to be for a day, and why?
- What would be the topic of your New York Times bestselling book?
- If you had paints right now, how would you fill a blank canvas?
- How do you define success?
- What is the cause of cruel behavior in the world?
- How can you tell when you have chemistry with someone?
- In all of human history, what’s the most important event?
- Why are we here on this planet?
- What’s one truth you’ve learned about being a human?
- When you think about the future, what makes you nervous?
- What would help you feel the most relaxed right now?
- What’s the biggest challenge you’ve overcome?
- What’s a time when you failed, and what did it teach you?
- When you feel self-doubt, how do you push through it?
- Can you recall the last time something made you cry?
- What’s the biggest trigger for your stress?
- What happened on the greatest day of your life?
- How do you think all of Earth’s different religions came to be?
- Do you believe in miracles?
- Do you believe in prayer and, if so, how do you do it?
- What makes you feel lonely?
- Do you believe that humans have a soul that lives on?
- What’s a secret about you that you haven’t told anyone?
- What makes you feel the most alive?
Being a skilled conversationalist takes practice. A good set of communication skills can help you show interest in what your someone is saying.
When you ask someone a question, for example, you may find it helpful to employ a few active listening techniques, such as:
- asking for more details
- maintaining eye contact
- repeating back what they said
- responding with encouragers, including “hmm” and “interesting”
- giving someone your full attention — that means not looking at your phone
There’s an art to ending a deep conversation. Without some finesse, things could feel awkward or incomplete.
The first step is picking the right moment. It’s a good idea to wrap things up when:
- there’s a natural lull
- you notice a sense of “completion”
- your conversation partner looks bored or uncomfortable
- a person, or device, interrupts the flow
- there are body language cues that show they’re ready to go
- you’d like to reflect
When the opportunity arrives, you can thank your conversation partner and suggest a lighter follow-up activity. For example, this could sound like:
“Thank you for opening up to me. I really enjoyed this conversation. I hope we can have more of these in the future. Would you like to split the bill and take a quick walk in the sun, before I have to head back to work?”
What if a conversation takes a downturn?
In the event of a downturn, try to use this as an opportunity to keep improving your connection by offering compassion, validation, or in some cases, an apology, says Tassiello.
“Downturns are a part of the deal when we’re in deep with someone,” she says. “Instead of fearing that aspect, bring yourself into the present moment and ask how you can be supportive around the topic next time, or what the person needs.”
Meaningful conversations can help deepen your interpersonal connections, which in turn, can help improve your overall health and well-being.
When you’re done with the 45 questions above, you can keep the conversation flowing with Gottman’s Card Decks, which are available in an app form on your device, says Panganiban.
You may also find it helpful to sift through “The Complete Book of Questions: 1001 Conversation Starters for Any Occasion” by Garry Poole.