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18 Deep Conversation Starters Therapists Swear By

Because you probably don’t really care how someone’s work is going—do you? ByCarolyn Todd

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Want to know the secret ingredient for feeling less awkward and more outgoing at pretty much any social gathering? No, it’s not alcohol—it’s a running list of deep conversation starters that will get people talking, sharing, and connecting.   

“I recommend having a few stored in your back pocket that you can turn to when the conversation runs dry or broaches a topic that feels controversial,” says Miriam Kirmayer, PhD, a clinical psychologist and friendship expert. Ideally, you want prompts and questions that are “simultaneously a safe bet, and also interesting,” Dr. Kirmayer says. 

So, what are questions that can take you beyond the usual pleasantries when you’re seated next to somebody you don’t know that well? How can you redirect someone when they broach a hot-button political issue? And what are ways to start a conversation that actually creates a deeper connection, instead of just passing the time? 

For answers, we turned to some professionals who literally make a living getting people to open up: therapists. They shared their favorite deep questions and conversation starters (or conversation changers) that you can keep handy this small-talk season. 

And before we get to their suggestions, here’s one bonus pro tip that several of our experts offered: Be prepared to share answers to these deep conversation starters yourself—or even go first. People generally respond better when you lead with a little self-disclosure upfront, says psychiatrist Jessi Gold, MD, chief wellness officer of the University of Tennessee System, and author of How Do You Feel?

1. What were some of your favorite memories from the year?

“A great place to start, this question can spark meaningful exchanges that don’t feel overly personal. People love sharing highlights!” —Miriam Kirmayer, PhD, a clinical psychologist and friendship expert based in Montreal

2. Does your family have any fun or meaningful traditions? 

“Most everyone has a meaningful or quirky holiday tradition to share, and this lets them tell the story. They can reveal as much or as little as they’d like and then compare their experiences with others. Not everyone has good memories of past holidays, though, and if this comes up you can easily change the question to ‘What tradition would you like to start?’” —Ryan Howes, PhD, a clinical psychologist based in Pasadena, California

3. What's one thing you’ve overcome that you feel really proud of?

“One of my favorites for going deeper is giving people the opportunity to share a challenge they've overcome. Questions like this steer people away from the danger zones, like politics, and can really humanize people. It lets them share something real that they've grown from. You can follow up with, ‘Well, how did you do it? Did you overcome it the first time? Did you have to keep trying?’ We all have these stories because we’ve all had tough things in our lives—even the most brilliant, successful people on the planet." —Cheryl Chase, PhD, a clinical psychologist and speaker based in Independence, Ohio

4. What’s something you’ve recommended to friends recently—like a recipe, movie, book, or show?

“People enjoy sharing their favorite finds and this question can help you find common ground.” —Miriam Kirmayer, PhD, a clinical psychologist and friendship expert based in Montreal

5. What's the worst holiday present you've ever received? 

“Humor is a great way to bond, so asking about the worst presents can make for fun conversational exchanges. As long as your giver isn't in the room, sharing with others about unique or irreverent gifts can lend a lot of laughter to festive occasions.” —Deborah Serani, PsyD. a psychologist based in Smithtown, New York and professor at Adelphi University

6. What’s been bringing you joy lately? 

“This is the other side of the spectrum. Asking somebody what's bringing them joy recently is a way of having a shared experience with the person. Because when we dip into our joy reservoirs internally, it's something that you want to share with another person. More often than not, they're going to want to hear about the glimmers of joy that are happening in your life, too.” —Akua K. Boateng, PhD, an individual and couples therapist and therapeutic coach based in Philadelphia

7. What’s something you learned this year that surprised you?

“Us therapists love a deep chat, but I like this one because it allows the other person to pick if they want to answer in a funny light-hearted way or if they want an opportunity for vulnerability and self-reflection.” —Natalie Englander, a cognitive behavioral therapist and mindfulness teacher based in Hertfordshire, England

8. What movie never fails to make you cry? (And why?)  

“Many people have difficulty talking about emotions, especially crying, but this question provides just enough distance to let their guard down. Most people can relate to movie-inspired tears and say the great acting or powerful story was the real source. The follow-up question allows a person to be a bit more vulnerable if they’d like, sharing how they relate to the story.” —Ryan Howes, PhD, a clinical psychologist based in Pasadena, California

9. How have you been feeling?

“I don't love the standard ‘How are you?’ because people tend to just say ‘OK’ or ‘fine.’ And neither of those are actual emotions. So I like to ask how they feel. I mean, there’s a reason my book is called that! The question makes people actually pause, hear you, and respond with an actual emotion instead of kind of blowing the question off.”  —Jessi Gold, MD, psychiatrist, chief wellness officer of the University of Tennessee System, and author of How Do You Feel?

10. What is one thing you changed your mind about this year?

“This question encourages self-reflection and deeper conversations. It’s also great for shifting the focus from surface-level chatter to something more engaging, and people can choose the level of vulnerability with which they want to approach this question.” —Miriam Kirmayer, PhD, a clinical psychologist and friendship expert based in Montreal

11. What niche hobbies or interests are you really into these days? 

“​​This is a good one if the conversation is turning to politics, because most people do like to talk about themselves. I like to find something that the person is interested in or pretty good at and ask questions about it—like how they got into it or what keeps them going. If you turn the conversation to something they love and give them space to talk about it, they’ll often be happy to change the topic and go a little bit deeper.” —Cheryl Chase, PhD, a clinical psychologist and speaker based in Independence, Ohio

12. What’s something you’re really proud of that isn’t work-related?

“If you get bored to tears by the ‘What do you do?’ small talk, then this convo starter is great for you! Plus it invites the other person to share something personal and meaningful beyond professional success, which allows for a deeper understanding and connection.” —Natalie Englander, a cognitive behavioral therapist and mindfulness teacher based in Hertfordshire, England

13. What are you hopeful about next year?

“Hope and optimism can be powerful antidotes to stress or tension. This question can generate uplifting conversations and open the door to checking in and supporting each other throughout the year.” —Miriam Kirmayer, PhD, a clinical psychologist and friendship expert based in Montreal

14. If money and time were not a factor, what passion would you pursue?

“This question taps into a person’s deeper desires, and by removing time and money barriers they can really let their dreams go wild. Some people reveal an unfulfilled wish, others may talk about charitable work or time with friends and family. It’s a low-stakes question that allows someone to imagine their best life, and you can learn something about them along the way.” —Ryan Howes, PhD, a clinical psychologist based in Pasadena, California

15. What’s the last thing that made you laugh?

“Laughter is a quick connector, and this question can lead to lighthearted storytelling or even shared humor (a great litmus test for friendship compatibility!).” —Miriam Kirmayer, PhD, a clinical psychologist and friendship expert based in Montreal

16. Tell me about a meaningful or surreal experience that you’ll never forget.

“It moves people into reminiscing and savoring past experiences. Also, if you’re in conversation with people that you already know pretty well, there are always pockets of experience that you haven’t actually told each other about. You may not know how a close family member would answer this question.” —Akua K. Boateng, PhD, an individual and couples therapist and therapeutic coach based in Philadelphia

17. Tell me a high and low from your day/week.  

“I like this better than ‘How was your day?’ Because usually when we ask that, people think we want to hear about only one or the other, the positive or the negative. If it’s someone you’re close to, they might tell you only the bad things. Or if it's someone you don’t know as well, they might tell you only the good things. Asking it this way gives them an opportunity to share about both sides and kind of forces a balance.” —Jessi Gold, MD, psychiatrist, chief wellness officer of the University of Tennessee System, and author of How Do You Feel?

18. Which fictional character do you think you’d get along with in real life?

“This is a playful way to explore someone’s personality and interests. It often leads to surprising and fun insights—I rotate lighthearted small-talk questions on the contact page of my website and this is the one I’ve gone with most recently!” —Miriam Kirmayer, PhD, a clinical psychologist and friendship expert based in Montreal