12.06.23
15 Questions That’ll Help You Get to Know Anyone Better
Because you’re not actually bad at socializing.
As much as ice-breakers suck in corporate settings (sorry, but I’m not telling HR about my “roses and thorns” this year), in other situations, they’re a hack for learning more about someone. After all, asking the right questions encourages people to share their experiences and perspectives, which is a cornerstone in building trust and understanding, says licensed psychologist Luke Allen, PhD. FWIW, that desire to connect with others in a meaningful way but not knowing how is a big reason that “the one Q I ask everyone” trend took off on TikTok, says therapist Kara Kays, LMFT.
But finding the right Q to kick things off can be tricky. You don’t want to scare someone, but you also don’t want to be basic or kill the convo with, “Soooo, what are your hobbies?” It turns out, though, that these prompts don’t need to be super intrusive, boring, or serious, says Kays. Imagine how something chill like, “What’s your favorite childhood memory?” can inspire a more lighthearted yet in-depth chat than, “Was your childhood a happy one?” While both options get into what life was like growing up, only one avoids the risk of re-traumatizing your new friend over coffee.
Lucky for you, these 15 conversation starter ideas from therapists and regular people will help build deeper, stronger connections with anyone worthy of your time.
1. What’s the most adventurous thing you’ve ever done?
“If I’m trying to get to know someone better, I want to find out if we share similar values. Since travel, spontaneity, and general zest of life are important to me, I use this to find out what adventure means to them. Whether it’s facing Costco on a Saturday morning or bungee jumping in Costa Rica, their answer will gauge how compatible we are.” —Amanda E., 25
2. If money weren’t a problem, what would you do on your average Tuesday?
“I love asking this because it gets to the core of who someone really is and what they would do if they didn’t have to worry about general survival things like taxes and making dinner. I have met so many people who surprised me because their response was something totally different from what they currently do. Like an engineer who would spend their time running a library or perusing an old bookstore! —Avery B., 23
3. If you could have a conversation with anyone in history, who would it be and what would you ask them?
“This gets to the heart of someone's interests. It's like opening a window into who they admire or find fascinating. Plus, the kind of questions they'd pose say a lot about what matters to them.” —Jacky Q., 34
4. What is the biggest compliment you could receive?
“Someone’s answer reveals how they would like to be perceived. It can give insight into how someone is trying to portray themselves, what personal qualities they respect the most, as well as what their goals might be.” —therapist Hannah Mayderry, LMHC
5. What’s one experience you believe everyone should have at least once?
“I love asking this to new people because it gets someone to talk about themselves and the things they have gone through in a way that isn’t traumatizing. And it gives me an opportunity to share some of my own experiences, potentially finding things in common along the way.” —Isabel C., 26
6. If you had three wishes, what would they be?
“What someone wishes for can signal their values. For example, if they say they wish to win the lottery, this could be a sign that they value financial stability and freedom. Wishing to spend more time with loved ones would indicate the importance they place on quality time. A wish for good health would show signs they prioritize health over material objects.” —therapist Kara Kays, LMFT
7. If you could wake up tomorrow having gained one ability or quality, what would it be?
“If you want to ask someone a deep question but are worried about scaring them off, I like to pick one that’s fun and thought-provoking without crossing personal boundaries. This helps me understand others a bit more while maintaining comfort.” —psychologist Luke Allen, PhD
8. What makes you get up in the morning?
“I like to ask this because it shows what motivates people. You can learn a lot about someone by how they start their day and what they’re passionate about. This helps you identify people you share the same values with. Like if their passion is getting up to run before the sun is up, we may not be a great match.” —Richard M., 30
9. What do you want me to know?
“This shows what someone’s innermost self wants to communicate. As a therapist, I usually ask people what layers, experiences, or thoughts are beneath their interactions, and this prompt helps get at the same idea.” —therapist Nicole Nina, LCSW
10. What are you most proud of?
“Asking someone what they are most proud of gives a glimpse into what experiences or achievements they cherish. It can also show what someone cares about and what they’d want to work toward in the future. Since I really appreciate passion and ambition, this question gets to the deep stuff quickly.” —Gaby S., 23
11. Do you have a favorite quote that inspires you?
“This topic lets you find out where someone gets their inspiration—whether it's from books, a great movie, famous people, or someone who means a lot to them. It's a good way to learn what keeps them going and what they find interesting.” —therapist Lana Lipe, LCSW
12. If you could pick one TV show to describe the relationship you have with your family, what would it be?
“Since family is really important to me, I want to know right away whether or not someone shares that belief. This is a fun way to have that conversation—as long as their answer isn’t Succession or something too intense.” —Carly S., 18
13. What's the most generous thing you've ever done for yourself?
"This question is inherently positive and focuses on self-kindness rather than personal shortcomings or negative experiences. It not only generates a more constructive conversation but also motivates and inspires others to be more compassionate with themselves.” —therapist Eden Katz, LMSW
14. You’ve had a rough day at work. What do you do to relax?
“I think how someone recharges and takes care of themself is a beautiful way to see how their mind works. Like, if they relax by scrolling on social media, that tells me something different than someone who says they meditate or read a book.” —Kayla O., 22
15. If there was a museum featuring artifacts from your life, what items would be must-see exhibits, and what stories would they tell?
“Unleashing creativity in conversation can lead to rich and revealing insights. This question not only encourages self-reflection but also allows individuals to share the narrative of their lives through the lens of personal belongings, opening the door to meaningful and unique connections." —therapist Dolly Ferraiuolo, LCSW
Quotes have been edited and condensed for length and clarity.
Wondermind does not provide medical advice, diagnosis, or treatment. Any information published on this website or by this brand is not intended as a replacement for medical advice. Always consult a qualified health or mental health professional with any questions or concerns about your mental health.
