200 Important Questions for the Early Stages of Dating

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Celebrity dating coach Damona Hoffman offers questions & tips to skip the small talk

Co-authored by Damona Hoffman and Samantha Fulton, BA

Last Updated: August 13, 2026 Fact Checked

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• Funny & Random
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• Interests
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• Values
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• Communication & Connection
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• Deep
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• Intentions
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• FAQ

|Show more |Show less

If you’re struggling to drum up conversation in the talking stage, we’re here to help. We’ve partnered with dating coaches to put together this list of some of the best, most interesting questions to ask someone in the early stages of dating. Whether you’re looking for something upbeat and humorous, something more deep and serious, or something in between, we’ve got you covered. Keep reading for 200 questions to get your talking stage off to the right start!

Best Questions to Ask in the Talking Stage

Celebrity dating coach Damona Hoffman says the best questions in the early stages of dating are engaging and specific and help you identify connection points and common interests. Keep things light at first. As you talk for longer, ask questions about values and intentions. Here are some of the best questions to ask:

• What could you spend hours talking about?
• What are your dream travel destinations?
• What does success look like to you?
• What core values guide how you treat people?
• What gestures make you feel loved?
• What’s your biggest guilty pleasure?
• What does a healthy relationship look like to you?

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Section 1 of 6:

Funny & Random Talking Stage Questions

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1. 
   Start light with silly or humorous questions. It’s helpful to break the ice with some simple, fun getting-to-know-you questions in the early stages of dating. Hoffman adds that questions should be engaging and specific. If you’re on a first date and want to make the conversation more interesting, try out one of these funny questions:

   • What’s the weirdest thing you’ve done out of boredom?
   • Would you rather be a ninja, a pirate, or a cowboy?
   • What type of bug do you think you’d be?
   • What would your villain entrance song be?
   • Who do you think would win in a fight: a horse or a kangaroo?
   • Which historical figure do you think you could take in a fight?
   • If you got arrested, what would people assume you did?
   • If you could be invisible for a day, what would you do?
   • Which celebrity would you want to swap lives with?
   • Which fictional universe would you want to live in?
   • How long would you survive in a zombie apocalypse?
   • What is your favorite smell?
   • What do you think your last words will be?
   • What’s the weirdest conspiracy theory you actually buy into?
   • What would you do if you woke up in the middle of a giant maze?
   • Who was your first celebrity crush?
   • If you were banned from a public place, what would be the reason?
   • Is ice a food or a drink?
   • What would you do with only 24 hours to live?
   • Do you think aliens exist?
   • Do you believe in ghosts?
   • What’s the funniest joke you’ve ever heard?
   • Would you time travel to the past or the future, and what would you do?
   • If you could choose one body part to have two of, which would you choose?
   • Which animated character do you relate to the most?
   • Would you rather have feet for hands or hands for feet?
   • What’s the last thing you’ve gotten away with?
   • Is a hotdog a sandwich?
   • If you could pick a day of your life to relive over and over, which would it be?
   • What is the most normal thing about you?
   • Do you consider cereal soup?
   • If you could be an amphibian, which one would you be?
   • What’s the weirdest thing you’ve ever Googled?
   • If this date had a theme song, what would it be?
   • If your personality were a font, which font would it be?
   • What’s the most chaotic thing in your camera roll?
   • Which celebrity do you think you could successfully rizz up?

   Meet the wikiHow Experts

   Damona Hoffman is a dating coach and best-selling author with over 15 years of experience. She’s a regular contributor on the Drew Barrymore Show and NPR, and she’s consulted for dating apps like OKCupid and Bumble.

   Hayley Quinn is a dating coach with over 15 years of experience and is one of the most trusted dating coaches in the world. She has coached over 7,500 clients worldwide and has been reviewed by Cosmopolitan and The Independent.
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Section 2 of 6:

Talking Stage Questions about Interests

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1. Connect over interests and hobbies. “Look for connection points,” advises Hoffman. Try asking about their passions and what they’re interested in to see if you have things in common. This will help you assess compatibility, plus it’s a fun way to keep the conversation rolling. Here are some hobby- and interest-related questions you can ask in the talking stage:

   • What’s your favorite way to spend a weekend?
   • What hobbies have you been dying to try?
   • What do you want to learn to do this year?
   • What’s your most recent hyperfixation?
   • What could you spend hours talking about?
   • Who or what do you still fangirl/fanboy about?
   • If you had unlimited funds, would you spend it on travel, education, or something else?
   • What hobby has changed your life?
   • Which artform helps you escape reality the most?
   • What movie, book, or TV show do you quote the most?
   • What do you wish you had more time for?
   • What do you think your retirement hobby or passion project will be?
   • Which non-living item would you save from your house or apartment if there were a fire?
   • What’s the last Wikipedia rabbit hole you fell down?
   • Which controversial celebrity do you want to have a conversation with?
   • What book would you require everyone to read if you could?
   • Which movie do you think everyone needs to watch?
   • What’s your favorite playlist you’ve ever made?
   • Who are your top 5 most-listened to artists this year?
   • Which celebrities or historical figures would you invite to a dinner party?
   • What’s your favorite sport or physical activity?
   • Do you prefer beaches, mountains, or forests?
   • What’s the most beautiful place you’ve explored?
   • What are your dream travel destinations?
   • What do you want to be when you grow up?
   • Do you prefer cooking or baking?
   • Do you prefer solo travel or group trips, and why?
   • Do you play any musical instruments?
   • What’s your go-to karaoke song?
   • What’s the first thing you do when you go to a new city?
   • Do you listen to podcasts? Which ones?
   • What’s a fun fact you recently learned that you want everyone to know about?
   • When was the last time you lost track of time while doing something? What were you doing?
   • Are you a morning person or night owl?
   • Do you prefer books or podcasts?
   • Where can someone find you after work?
   • What excites you right now?

Section 3 of 6:

Talking Stage Questions about Values

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1. 
   Find out if you share the same values. Dating coach Hayley Quinn says it’s good to use values as a way to steer the conversation in the early stages of dating. Ask questions to discover how much common ground you share. Do they have the same views on family, finances, religion, and politics? These are important things to find out. Here are some values-based questions to help you get to the meat of things:

   • What are your biggest aspirations in life?
   • What does success look like to you?
   • Are you religious?
   • How do you lean politically?
   • What moral beliefs do you value most?
   • What does family mean for you?
   • What kind of person do you want to be?
   • Who is your favorite person?
   • What was the last thing you did that your childhood self would be proud of?
   • What are your career goals?
   • What’s your dream job?
   • Would you still work if you didn’t have to?
   • What would you do if you didn’t have to work?
   • Do you think you have to forgive to move forward?
   • When do you feel at peace?
   • What does spirituality mean for you?
   • What gives your life meaning?
   • What does truth mean to you?
   • What or who would you bend the rules for?
   • What personality trait do you have that sets you apart from the crowd?
   • If you could change one thing about yourself, what would it be?
   • How do you think others see you?
   • What does your perfect day look like?
   • What are your biggest pet peeves?
   • If you won the lottery, what would you spend it on?
   • What does personal growth look like for you?
   • What are your biggest dealbreakers?
   • What’s your favorite quality in a friend or partner?
   • What could you never go a day without?
   • When was the last time you broke the rules? What did you do?
   • When have you felt proudest of yourself?
   • When was the last time you got angry, and why?
   • What life experience has shaped you the most?
   • If you had a million dollars to give away, what would you donate it to?
   • What do you hope people say about you when you’re not around?
   • How would you describe your friend group in three words?
   • Who do you admire most in your life?
   • What core values guide how you treat people?
   • What qualities do you value in the people in your life?
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Section 4 of 6:

Talking Stage Questions about Communication & Connection

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1. Ask about their communication style to avoid future confusion. “If your communication skills are incompatible, it can be like speaking different languages,” notes Hoffman. The talking stage is a great time to find out whether your styles of communication align and whether you connect in the same ways. Try asking some of these questions to figure out if your approach to communication and connection aligns:

   • What’s your love language?
   • Do you prefer phone calls or texting?
   • How frequently do you like to communicate at the beginning of a relationship?
   • Are you more verbose or succinct?
   • How do you express love or affection for others?
   • How do you tend to approach conflict?
   • When are you most comfortable being yourself?
   • What topics do you avoid discussing?
   • How much space do you need after a long day?
   • How do you share big news or hard feelings?
   • What are your tells when something is bothering you?
   • What makes it easier for you to talk about hard things?
   • How do you react to criticism?
   • What does a good apology look like to you?
   • How do you show appreciation in a relationship?
   • What’s the easiest way to make you smile?
   • What emotion do you have the hardest time expressing?
   • What worries keep you up at night?
   • What gestures make you feel loved?
   • When you’re venting, do you prefer advice or a listening ear?
   • After an argument, do you need space or conversation?
   • What challenges your patience the most?
   • When in the day is it easiest for you to have a conversation?
   • Do you tend to express your feelings more through words or through actions?
   • What topics are easiest for you to talk about?

Section 5 of 6:

Deep Talking Stage Questions

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1. Dive deeper with more personal questions. Once you feel more comfortable with the person you’re talking to, test the waters with some questions that get to the heart of their personality and experiences. You don’t need to pull the trigger on any of these on the first date, but they can be a great way to learn more about each other when you first start seeing one another. There’s also plenty of opportunity to ask follow-up questions, which Hoffman says demonstrates good listening skills. Here are some deeper questions to ask in the talking stage:

   • What’s your deepest regret?
   • What’s the best decision you’ve made in your life?
   • What question are you struggling to find the answer to?
   • What’s the biggest “what if?” in your mind?
   • Who is someone you wish was still around?
   • What’s your worst vice?
   • What are you most afraid of?
   • What’s been the biggest challenge you’ve had to overcome?
   • What was growing up like for you?
   • What is your favorite memory?
   • How often do you talk to your family? Would you change that if you could?
   • What are you secretly insecure about?
   • What’s the last thing that made you cry?
   • What’s your biggest fear when you enter a romantic relationship?
   • Who was your first love?
   • Are you afraid of failure?
   • Do you consider yourself a jealous person?
   • What’s the most embarrassing thing about you?
   • What’s something most people don’t know about you?
   • What’s your biggest guilty pleasure?
   • How’s your relationship with your parents?
   • What are you currently trying to prove to yourself?
   • What motivates you?
   • Do you hold grudges?
   • Are you currently holding any grudges?
   • If you wrote a memoir, what would the title be?
   • What do you think is your fatal flaw?
   • What is something that overwhelms you?
   • When do you feel most anxious?
   • When do you feel most at peace?
   • What obstacles are you trying to overcome these days?
   • What was the last lie you told?
   • Do you feel like you’re living up to your potential?
   • Would you rather have a pause, rewind, or fast forward button on your life?
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Section 6 of 6:

Talking Stage Questions about Intentions

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1. 
   Figure out if you want the same things going forward. If things are looking promising, and you’re thinking it’s time to move out of the talking stage, ask some questions about the other person’s intentions and relationship goals. Quinn notes that it’s important to make your intentions clear when you’re navigating dating. These questions are a great way to open up the conversation and find out if you’re on the same page:

   • What are you looking for right now?
   • How would you describe your dating style?
   • What type of relationship are you currently open to?
   • What does a healthy relationship look like to you?
   • What are your non-negotiables in a partner?
   • What does emotional intimacy mean to you?
   • What do you like or dislike about dating?
   • Do you enjoy being single?
   • Have you ever ghosted someone?
   • How would your friends describe your dating life?
   • Where do you see yourself 5 years from now?
   • Are you dating other people?
   • How do you feel about long-term relationships?
   • How do you feel about hookups and casual relationships?
   • Are you looking for a serious commitment right now?
   • What’s your number one priority in life right now?
   • What does cheating mean to you?
   • Do you see yourself having kids?
   • Do you see yourself getting married?
   • Do you practice monogamy?
   • Where do you see this going in the future?
   • How long do you usually date someone before making it exclusive?
   • Do you tend to get to know one person at a time or multiple people?
   • How do you show someone you’re genuinely interested in them?
   • When you imagine your dating life over the next year, what does it look like?
   • What made you decide to start dating again?
   • What role do gender roles play in a relationship for you?
   • How do you define trust and loyalty?

Common Questions: Navigating the Talking Stage

How long should the talking stage last?

Dating coach Hayley Quinn says that the length of the talking stage depends on the context and the preferences of the people involved. She notes that it’s normal for people to talk virtually for a couple weeks before a date, or that a talking stage can be shorter if you’ve already met face-to-face. Plus, she adds, some people may enjoy staying in the talking/flirting stage because of the lower stakes—this makes it important to discuss your intentions early on and determine how long you’re comfortable being in limbo.

What red flags should you watch for in the talking stage?

During the talking stage, dating coach Hayley Quinn cautions to watch out for people who like to talk and flirt but aren’t open to meeting up or progressing the relationship. “You need to prioritize people who create consistent time to get to know you better,” she advises. Other obvious red flags include someone who is disrespectful or unkind, someone whose values don’t align with yours, or someone who can’t or won’t communicate effectively.

How do you ask someone about their relationship goals?

Be direct and straightforward. Dating coach Hayley Quinn recommends being especially clear in your intentions during the talking stage. “Some people will wait for a really clear sign you like them before they feel confident enough to act,” she adds. If you want to know where you stand, let them know what you want and ask them what they’re looking for and where they see things going.

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