Getting to know someone new—we mean really getting to know them—can be a thrill (for extroverts, under the right circumstances). But it can also feel like a downright daunting task. This is especially true for introverts, or anyone entering into a new situation—whether that’s a first date, a new job, a new city, or even a new identity (like first-time parenthood... or trying to emerge from two years of quarantine lifestyle).
To get the conversation going in the right direction, remember it’s not just about talking, but about listening, too. And that means asking the right questions, thought-starters primed to get at real substance rather than small talk.
“Whether a new colleague at work, a business mixer, or even in a social scene, getting to know someone isn’t the easiest task,” explains Dr. Wayne Pernell, who holds a doctorate in clinical psychology and specializes in helping people achieve greater success and satisfaction in life and work.
A good rule of thumb? “You never start with the weather,” he says. “It’s too easy. It doesn’t give you information, and ultimately it doesn’t mean anything. Instead, focus on something that's meaningful, but not a common topic.”
Beyond that, he says, stay focused and interested. “It’s not just the questions, it’s how you ask and how you stay engaged as they answer that matters.”
Here are 60 questions that can inspire real connection.
Questions About Likes/Dislikes
Asking someone about things they enjoy—or despise—is a way to ask something personal without being intrusive, Pernell says. For instance, even asking someone about their favorite sandwich asks for a memory recall and opens doors of conversation. “You may learn about their preferences, you may learn about various trips they’ve taken, and you may learn about their background,” he says.
What’s your favorite sandwich and where did you eat it?
What’s your favorite place on earth?
What’s one place you've visited that you never want to return?
What’s the best show on TV right now?
If you could only eat one food for the rest of your life, what would it be?
What’s the worst movie you ever saw?
What’s the best thing you've read in the last five years?
What’s the one item of clothing you couldn't live without?
If you could only bring three things with you on a deserted island, what would you pick?
If you could save one material thing from a fire, what would you save?
What’s your biggest pet peeve?
What is your favorite movie of all time?
What is the best concert you have ever been to?
What’s the worst date you've ever been on?
Would you rather be hot or cold?
What’s your favorite karaoke song?
Questions About Hopes, Dreams, and Fears
Simple questions can elicit truly profound responses when the questions get at the heart of someone’s biggest fears, regrets, hopes, or dreams. So go for it with these deeper questions, with a few caveats, says Dr. Alyson Nerenberg, licensed psychologist, specializing in relationships, and author of No Perfect Love: Shattering the Illusion of Flawless Relationships. “Keep your questions simple and open-ended—and don’t ask anything you wouldn’t want to answer yourself,” she says. “Make sure the questions are not boring. No one wants to be asked the same basic questions they’ve already answered a million times before.” Try these:
What is on your bucket list?
What are you most thankful for?
What is your biggest regret in life?
What are you most afraid of?
What do you feel most passionate about?
How do you like to spend your free time?
What would your perfect day be like?
What does your dream life look like?
Questions That Spark (Friendly) Debate
One way to keep a conversation flowing is to ask questions about a topic likely to inspire opinionated—controversial—answers. “Start a friendly debate that sparks fun and unusual conversation,” suggests Kate Maclean, resident dating expert for Plenty of Fish. You probably want to avoid fraught political debates right off the bat; rather, even silly hypotheticals can lead to “quirky and lighthearted conversation that can help relax any situation.”
To that end, try:
What is your favorite urban legend that you believe is true?
Would you rather live without the internet, or without bathing?
What was the best decade for music?
Is it ever OK to lie?
Who’s the most overrated celebrity?
What’s the worst seat on a plane?
What’s the most annoying thing people do in public?
Are avocados overrated?
Who’s your dream dinner party guest, living or dead?
What would you do tomorrow if you won a million dollars today?
Is a hot dog a sandwich?
Are you a dog person or a cat person and why?
Were Ross and Rachel really on a break?
Questions About Family and Community
For some, questions about family can be emotionally charged or otherwise heavy. But gently unpacking the ties that bind someone’s family, friendships, and other community relationships can be both revealing and lively. For instance:
Who is the most important person in your life and why?
Who in your life most makes you feel a sense of home?
Do you have a mentor?
Have you ever broken up with a friend, and why?
How many close friends is ideal?
Do you believe in soulmates?
Questions About Personal History and Personality Essence
Sometimes, a straightforward question can get at people’s own perceptions of themselves—and how they wish to be perceived by others they meet. Plus, the answers to these fundamental questions are unlikely to come up on their own through the course of superficial conversation. Consider these questions that probe someone’s personality, personal history, and what they consider to be the most fundamental aspects of their being:
What is the best compliment that you’ve ever received?
What do you want people to say about you at your funeral?
What is something people would never guess just by looking at you?
What makes you laugh the most?
Have you ever made a decision that changed your life?
What was the happiest day of your life?
What’s your favorite thing about yourself?
What did teachers used to say about you on your report card—and is it still true?
What’s something you wish you could change about yourself?
Questions About Work
Depending on the setting you’re in, work-related questions can be both the most appropriate ice breakers and also ways to spark lively conversation. For the best results, go deeper than the standard interview/water cooler fare. “Do not simply go through a checklist of questions of what you are supposed to ask,” says Narenberg. “Truly listen to the person’s response. Everyone wants to feel like they are seen and listened to and that their answers matter.”
What’s the most exciting part of your job?
What would you want people to say about you at your retirement party?
What’s the most important thing you've ever done at work?
What’s your ideal work-life balance?
What’s the best piece of career advice you ever got?
What was something you thought was a career setback that actually turned out to be an opportunity?
What are the most important qualities in a leader?
What was your first job?
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