178 Questions to Ask Someone When You Actually Want to Get to Know Them

There’s a reason “So, tell me about yourself” is such a terrible conversation starter. It’s broad, vaguely terrifying, and somehow makes even the most interesting person forget everything they’ve ever done in their life. Whether you’re on a first date, getting to know a new friend, or realizing you’ve somehow been dating someone for six years without knowing their go-to karaoke song, asking the right questions can make learning about someone a whole lot easier.And no, that doesn’t mean showing up to drinks with a Notes app full of questions and working your way down the list (but do you). The point isn’t to interrogate someone; it’s to give the conversation somewhere interesting to go. “A unique question can snap someone out of autopilot and make them reflect and want to connect,” says Karen Vincent, LCSW, therapist and clinical director at Octave,The real magic, though, is in what happens after you ask. Rather than immediately moving on to your next question, Vincent recommends actually listening to the answer and following whatever seems to light the other person up. “The first question cracks open the door, but the follow-up questions are where you get the real connection,” she says. If they tell you their dream vacation is two weeks in Japan, ask why Japan! What would they want to do there? Have they always wanted to go? Congratulations, you’re having a conversation.Of course, not every question is right for every person or every stage of a relationship. Pay attention to how they respond, says Vincent. If they’re sharing details and seem excited to keep talking, you can probably dig a little deeper. If they give a short answer, change the subject, or seem uncomfortable, take the hint and move along. With that in mind, consider the questions ahead conversation starters, not a checklist—from general likes and dislikes to relationships, values, daily habits, and future goals, there are plenty of ways to get to know someone better.Jump to:Questions About General Likes/DislikesQuestions About Growing UpQuestions About Family and FriendshipsQuestions About Dating and RelationshipsQuestions About Values and BeliefsQuestions About Their CareerQuestions About Goals and the FutureQuestions About Their Daily Routine and HabitsQuestions About General Likes/DislikesConsider these questions great starting points and icebreakers to scratch the surface. They’re especially useful for first dates and conversations on dating apps. Vincent recommends starting with casual topics and letting the other person’s answers guide where the conversation goes from there. The questions near the top are lighter than the ones near the bottom, so start wherever feels natural and see where the convo takes you.What’s your favorite snack food?What’s the best dish you can cook?If you could have dinner with one person (living or dead), who would it be?Cats or dogs?If you could have any animal as a pet, what would you choose?Are you an introvert or an extrovert?What’s your strangest talent?What’s the last dream you remember?What’s something you could talk about for hours?What’s your favorite conspiracy theory?Describe yourself in three words.Oh, no! There’s a spider in the house. What’s the move?How do you feel about reality TV?Have you ever become intensely invested in the fate of a TV show character?Which TV or movie character do you identify with and why?Thoughts on scary movies?Do you like going to the movies or would you rather wait until it’s available on streaming services?If your life were a movie, what scene would you watch over and over again?Have you ever met any celebs? If so, what were they like?What show are you watching right now?Are you Team Spotify or Team Apple Music?What’s your go-to karaoke song?What type of music do you like the most?What music really affects your mood?What’s the best concert you’ve ever been to?Who would you drain your savings to see live?Have you ever been to a music festival?What song or artist do you love that people might not expect?Have you ever read a book that changed your life?Are you into any podcasts?What app do you use the most?What was the best trip you’ve ever been on?Would you prefer to go camping or chill at a resort?When you vacation, do you prefer a relaxed vibe or something adventurous and/or touristy?What’s your ideal way to spend your birthday?What age do you feel like?What’s your favorite season and why?Where is your happy place?Do you play board games?Where are you most likely to be at a party?What’s your biggest pet peeve?If you were an animal, what animal would you be?If you could instantly become an expert at one thing, what would it be?What do most people overestimate or underestimate about you?What’s a moment you’d love to be a fly on the wall for?What scrambles your brain every time you think about it?Are you a better talker or listener?What’s your “and then it got worse” story?What’s something you can never have too many of?When was the last time you felt really excited, and what were you excited about?What’s the funniest thing your inner child wants?What’s your go-to French fry dip?What movie always makes you sad? What movie makes you happy?What would be your last meal?What do you like about yourself today?Does social media make you feel better or worse about yourself?What’s the best decision you’ve made in your life?What’s the best decision you’ve made today?What are some of your biggest fears?What are some of your biggest irrational fears?What makes you feel most appreciated by other people?What do you love most in your life right now?What’s the last thing you remember wishing for?Who is your biggest influence and why?What’s something you love completely unapologetically?Do you have any vices?What’s your most prized possession?What’s the best gift you’ve ever received?What’s the worst gift you’ve ever received?What makes you cry and why?When was the last time you got really angry, and why?What is your best quality?Complete this sentence: “I most enjoy having someone to do _____ with.”What’s one question you wish more people asked you?Questions About Growing UpLearning about someone’s childhood can tell you a lot about the experiences, people, and places that helped shape them. Some of these questions are light, while others get pretty personal, so pay attention to how the other person responds as you go. Vincent notes that someone might happily open up about one area of their life but become noticeably quieter around another, and continuing to push can work against connection. In other words: Read the room, respect their boundaries, and don’t assume every childhood story is first-date material.Where did you grow up? Is it the same place you were born?How did you like growing up there?Did you have a childhood best friend?Did you have pets growing up?Did you collect anything, like cards or coins?What phase did you go through as a kid or teenager that makes you laugh now?What chores did you have growing up?Did you have a favorite toy growing up?What was your favorite birthday growing up?What embarrassing moment has stuck with you over the years?Did you ever study abroad?What was your favorite vacation growing up?Were you pretty well behaved in school, or were you a troublemaker?Did you have a favorite teacher?What was your favorite subject?What was your worst subject?Did you ever go to detention for anything?Did you play any sports or instruments as a kid? Do you still play them now?Did you ever go on any really exciting field trips?What trend or phase were you completely obsessed with growing up?Who was your first crush?What has surprised you the most about adulthood?What would you tell your childhood self?Who did you turn to as a child when you were going through something tough?What’s something difficult you went through growing up that taught you something about yourself?What’s something about the way you grew up that you appreciate more now than you did at the time?Questions About Family and FriendshipsThe people someone chooses to keep close can tell you a lot about what they value in their relationships. And if you’re dating, learning about their family and friendships can also help you understand what role those relationships might play in their life going forward. Just remember that family can be a sensitive subject, and “family” can mean something different to everyone, so let the other person decide how much they want to share.What is your relationship like with your family?What did spending time together as a family look like growing up?What’s your favorite family story?What traits from the people who raised you do you hope you never pick up?What traits from the people who raised you do you hope to carry with you?What five words would you use to describe the person or people who raised you?What are/were your grandparents like?Who in your family are you closest to?Do you have any siblings?Do you have any cousins you’re close to?Did you have a close bond with any of your grandparents?Who do you call first when something big happens?Does your family have any traditions you really love?If you ended up in jail, what would your friends and family think you did?Do you have a best friend?How did you meet your best friend?How did you meet the majority of your friends?How would your friends describe you?Do you and your friends have any annual traditions?What’s your favorite memory with your friends?Are you comfortable being friends with your coworkers or would you rather keep those relationships professional?What quality do you value most in a friend?What makes you feel close to someone?Questions About Dating and RelationshipsOkay, now we’re getting a little more personal. If you’re getting to know someone romantically, questions about their dating history and what they’re looking for can tell you a lot about whether you’re actually on the same page. That doesn’t mean you need their complete romantic résumé on date one, though. Start with the lighter stuff and save questions about exes and past breakups for whenever it feels natural.Tell me about the best date you’ve ever been on.What’s your ideal first date?Tell me about the worst date you’ve ever been on.How do you feel about dating apps?What's your best pickup line?What’s the best way someone could flirt with you?Would you prefer to meet people online or in person?Have you been in a serious relationship before?If you’re comfortable sharing, what did you learn from your last relationship?Are you friends with any of your exes?What do you look for and value most in a long-term partner?What qualities do you have that make you a good partner?What kind of relationship are you looking for now?Are there any couples whose relationship you really admire?Questions About Values and BeliefsTalking about politics, religion, and personal values can feel a little intimidating when you’re getting to know someone, but these topics can also tell you pretty quickly whether you’re fundamentally compatible. You don’t need to launch into a debate five minutes after meeting, obviously, but once the conversation feels comfortable, asking about the things that matter to someone can help you get to know them on a much deeper level. Just remember that these questions go both ways: If you’re going to ask someone to share their beliefs, be prepared to share yours too.Were you raised with any particular religious or spiritual beliefs?Do you currently have any religious or spiritual beliefs?Do you believe in life after death?Do you have a life motto?Do you believe in karma?Do you believe in astrology?Are politics important to you?Are there any social issues that you really care about? Why do they matter to you?Do you feel strongly about any specific charitable causes?Have you ever volunteered for an organization?Questions About Their CareerTalking about work can tell you a lot about someone’s day-to-day life, what motivates them, and how important their career is to them. The key is keeping it conversational rather than making them feel like they accidentally wandered into a job interview. You’re trying to learn what their life looks like, not where they see themselves in five years. (Unless you’re genuinely curious, in which case, go off.)How did you decide what to do for a living?Do you like your current job?What do you like most about it?Do you like your boss?Would you say you feel fulfilled at work?What’s the most fulfilling part of your job?What’s the most stressful part of your job?Are you friends with your coworkers?Do you want to stay in your current role for a while?What’s your favorite part of the workday?If money wasn’t a factor, would you still choose the career you did?What was your first job ever?Did you have any odd jobs growing up?Have you ever had a side hustle?What would make you feel like you’ve “made it” in your career?Have you ever dealt with imposter syndrome?Do you see yourself doing this kind of work long-term, or is there something else you’d eventually like to do?If you could start a business, what would it be?Questions About Goals and the FutureQuestions about goals—especially big dreams—can tell you a lot about what someone is working toward and what motivates them. And while career goals are part of that, these questions are more about the bigger picture: where they want to live, what they want to experience, and what they hope their life eventually looks like. Some get more personal than others, so, as always, you don’t need to ask about marriage and kids before you’ve finished your first drink.What makes you feel accomplished?What’s the next big purchase you want to make?What’s your dream car?What’s your dream vacation?What would you do if you won the lottery?What are you most determined to accomplish?Where would you be happiest living?Is there an area of your life where you feel like something is missing?What are your long-term goals?What’s something you hope is different about your life five years from now? What are you most proud of and why?If money wasn’t a factor, what would your dream life look like?Do you see yourself getting married someday?Do you see yourself having kids someday?What does your dream house look like?Would you ever want to live abroad for a while?Questions About Their Daily Routine and HabitsOkay, asking someone what time they wake up might not lead to the most thrilling conversation of your life, but learning about their everyday habits can tell you a surprising amount about what being part of their life might actually look like. Are they up at 5 a.m. while you consider anything before 9 an emergency? Do they spend every weekend out with friends while your ideal Saturday involves never leaving the couch? You certainly don’t need identical routines to be compatible, but it can be helpful to know how someone actually spends their time.Are you a morning person or a night owl?What time do you usually get up?What’s the best way to wake up in the morning?What does your morning routine look like?How do you take your coffee? Or are you more of a tea person?Do you work from home?What’s the first thing you do when you finish work?Do you have a nightly routine?How often do you see friends?Do you have a favorite neighborhood spot you go to all the time?Do you like to cook?What’s your go-to meal when you don’t feel like cooking?What meal is your favorite: breakfast, lunch, or dinner?Do you have a favorite restaurant in your neighborhood?Are you a neat person or a messy person?Are you usually on time, or fashionably late?What’s your favorite way to spend a day off?How do you usually spend your weekends?Are you a homebody or do you prefer to be out and about?How do you deal with finances? Do you try to stick to a budget?Do you live alone or with other people?What do you need during periods of stress? Do you call someone to vent? Do you spend time alone to think it through?How much downtime do you usually need to feel like yourself?