02.26.25
20 Conversation Starters for Anyone Struggling to Connect
Because you’re not actually bad at socializing. Additional reporting bySam Brodsky
In case you missed it, an important part of being human is connecting with other humans! It makes us feel good! But when you inevitably run out of things to say or don’t know where to begin, keeping some good conversation starters handy can be extra helpful.
That’s especially true if you’re trying to get to know someone. The right Qs can encourage people to share their thoughts and experiences, which helps build trust, says licensed psychologist Luke Allen, PhD.
That said, you don’t have to stress too much about asking the most perfect question ever. Any prompt that shows curiosity and openness can create a connection, says psychologist Kyler Shumway, PsyD. “Even a simple question, when asked sincerely, can lead to a meaningful and memorable exchange,” he adds.
Luckily, with the help of mental health pros and chatty people, we’ve come up with a list of smart conversation starters that do all that great stuff. Bookmark these for your next function and find out!
(Plus, if you’re looking for more conversation-starter inspo, check out these Would You Rather questions for adults, first date questions, and ice breakers for work. You’re welcome!)
1. What was the last song you sang out loud or danced to?
“This question is a little silly, which hopefully helps both people relax a bit. You can also learn more about the person—other than what songs they listen to. You might find out whether they like to sing and dance with others or prefer a solo session. Maybe they don’t sing or dance a lot. Maybe they prefer silence, stillness, or quiet spaces. The more you know!” —clinical psychologist Nina Polyné, PsyD
2. What’s something that surprised you about yourself in the last year?
“I love this conversation starter because it invites self-reflection and can lead to meaningful discussions about personal growth, unexpected challenges, or even moments of joy. It’s also open-ended enough to allow people to share at whatever depth they’re comfortable with. Be prepared with your own answer too. Nothing kills a conversation quite like asking someone to pour their heart out when you aren’t ready to do the same.” —speaker and licensed clinical psychologist Kyler Shumway, PsyD
3. If tomorrow morning all of your insecurities were gone, what would you do differently?
“This is inspired by solution-focused therapy. I love it because it gives them permission to open up in an unedited or uninhibited way. It allows them to be more vulnerable about their dreams and passions, letting us peek into their inner world.” —therapist Katie Miles, LMFT
4. What’s something you used to be embarrassed about but now think is cool?
“This question requires some vulnerability, allowing you to ditch perfection, celebrate growth, and relate to the other person. We all have that one thing we wished we could have changed about ourselves as kids, and, with shadow work, we see that our quirks are what make us unique and memorable.” —clinical psychologist Nina Polyné, PsyD
5. If you could relive any moment from your past, what would it be?
“This question can prompt deeper storytelling and reflection, allowing the other person to share the experiences that shaped them. Whether it’s a moment of personal triumph, connection, or pure joy, their answer can offer insight into what brings them fulfillment and what they hold dear. It also creates an opportunity for shared nostalgia, which can strengthen a bond.” —speaker and licensed clinical psychologist Kyler Shumway, PsyD
6. 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
7. 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
8. 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
9. 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
10. What’s an 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
11. 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
12. 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.” —licensed psychologist Luke Allen, PhD
13. 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
14. 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
15. 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
16. 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
17. 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
18. 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, LCSW
19. 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
20. 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.
