Maurice’s Blog

The best questions to ask to get to know someone (by category):

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 to?
• 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?
• What's your favorite quote?
• What was the best meal you ever ate?
• What's your least favorite genre of music?
• Do you like coffee or tea better?

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 Alyson Nerenberg, M.D., licensed psychologist specialized 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?
• What goal do you want to accomplish in the next few years?

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?
• What's the hardest challenge you overcame?
• Have you ever failed at something? What did you do after that?
• What word would friends of yours use to describe you? Do you agree or disagree?
• What was the most life-changing event in your life so far?

Questions About Work

Depending on the setting you're in, work-related questions can be both the most appropriate icebreakers 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?
• What is your relationship like with your co-workers?
• Where do you see yourself in five years?
• Is this the career you saw yourself doing as a child?

Questions About Values

If you're hoping to go a little deeper and strengthen an intimate relationship, try asking questions about their values. This can include questions about What's important to you, family life, spirituality, political beliefs, and more. Grant H. Brenner, M.D., D.F.A.P.A, board certified physician-psychiatrist, not-for-profit board member, and co-author of Making Your Crazy Work For You: From Trauma and Isolation to Self-Acceptance and Love, recommends asking questions about values if it's an important topic for you, but to leave room for the other person to politely decline. “It doesn't mean they aren't interested in getting into the subject, but they may need more time to warm up to that depth,” he says. “If you are someone who feels comfortable being open pretty fast, recognize that just because other people aren't there yet doesn't mean there isn't room for those conversations down the road.”

If you're wondering whether you should or shouldn't ask someone questions about values, consider the context of the relationship. “Before diving into an area deemed as personal values, think about who you are talking to, for What purpose, and the level of intimacy that is desired,” Mollie Eliasof, L.C.S.W., a licensed psychotherapist and relationship expert advises. “For something like a love relationship, this can be pivotal information, while in a work context in an interview, this may be inappropriate. Be intentional, and give the person the ability to bow out of answering.” Personal values are just that–personal. It can take some time for someone to be ready to discuss them with you, but if you are ready to ask questions about this topic, consider these questions:

• What do you think your purpose is?
• Have you ever made a promise that you didn't keep?
• Do you believe in second chances?
• What's your strictest boundary in relationships?
• What was the biggest favor you've ever done for someone else?
• What was the biggest favor you asked from someone else for yourself?
• Would you prefer a job you hate with a high salary, or a job you love with a low salary?
• If you had to make an emergency phone call, who would it be?
• If you could change one thing about the world, What would it be?
• Do you believe in any higher power? An afterlife?
• What is your love language?
• What are you most proud of yourself for?
• Do you read/watch the news? What topics do you pay most attention to in the news?
• How is your culture/background important to you?
• Have you ever cheated on anything/anyone?
• Do you prefer conversations in person or over text?
• If you had an excess of money, What charity would you donate to and why?
• Do you believe in soulmates?

Miscellaneous/Casual Questions

When it comes to new friends or co-workers, even simple questions can bring people closer. It provides the opportunity to discover mutual interests or shared experiences to bond over. “Asking more casual questions can also bring people closer, as a less emotionally-laden way of discovering shared pursuits, favorite books and media, travel preferences, sports and hobbies, and other areas which suggest compatibility via shared interest,” Dr. Brenner says. “In many cases, starting with less charged topics is a better place to start.”

• Would you rather drive or be the passenger in a car?
• What is your dream vacation destination?
• If you could be any animal, What would you be and why?
• What superpower would you want to have?
• Would you rather be able to travel into the future or into the past?
• If you had to live in a different city/state/country, where would you want to live?
• Would you rather be able to speak to animals or be fluent in every language?
• Are you a planner or do you go-with-the-flow?
• What is your astrological sign?
• What movie character do you think you are most similar to?