270+ Fun & Interesting Questions to Ask a Girl You Like

Experts share how you can get to know a girl with fun icebreakers

Co-authored by Hayley Quinn and Dev Murphy, MA

Last Updated: December 11, 2025 Fact Checked

• Get-to-Know-You Questions
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• Flirty
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• Funny
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• Juicy
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• Fun & Interesting
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• Deep
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• About Family
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• About Relationships
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• About the Future
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• How to Ask Questions to Get to Know Her

|Show more |Show less

Asking a girl questions about her life, goals, interests, and values is one of the best ways to get to know her better, especially if you've just started going out (or are hoping to become an item). We've compiled a list of the best icebreakers to ask on a date, while chatting over text or on a dating app, or when you're just hanging out as friends. We also got advice from dating experts and life coaches on how asking questions can help you get to know a girl better, and how to tell which questions you should ask.

Best Questions to Ask a Girl to Get to Know Her Better

Dating coach Cristina Morara recommends asking get-to-know-you questions like "What were you like in high school?" "What's something that someone would be really surprised to learn about you?" or "What's your pet peeve?" Here are some more great questions to ask a girl to get to know her:

• Do you collect anything?
• Which TV family reminds you the most of your own?
• What’s something that makes you feel the most like yourself?
• What qualities do you look for in a partner?
• What is a question you wish you were asked more often?

Steps

Section 1 of 10:

Get-to-Know-You Questions to Ask a Girl

1. 
   These icebreakers will help get the ball rolling. It helps to start with some small talk to warm things up and get to know each other on a basic level before diving into more serious questions, like "How many kids do you want?" "One of the questions I like people to ask is…'What were you like in high school?'" says Morara. "[It's] so revealing." She also recommends icebreakers like "What's something that someone would be really surprised to learn about you?" or "the simple 'What’s [your] pet peeve?'"

   • What were you like in high school?
   • What's a book that changed how you see the world?
   • What do you do for work?
   • Who’s the one person who can make you laugh when you’re not in a great mood?
   • What's something that someone would be really surprised to learn about you?
   • What’s something that makes you feel the most like yourself?
   • Is there a skill you’ve always wanted to pick up but haven’t gotten around to yet?
   • What would your dream long weekend look like from start to finish?
   • What life experience taught you a lesson you still use today?
   • What’s your dream job?
   • Do you have a dream you haven’t pursued yet that you hope to start working towards this year?
   • Where do you usually find inspiration when you need it most?
   • What kind of people energize you the most?
   • What’s a little tradition or ritual you have that others might find odd?
   • What is your favorite holiday?
   • What’s the scariest thing you’ve done that you’re glad you did?
   • What’s your ideal morning look like if you’re not in a hurry?
   • If money and time weren’t an issue, what band would you follow on tour?
   • Is there something you’ve always wanted to try but haven’t yet?
   • What’s a movie you can watch again and again without getting bored?
   • What rituals do you enjoy doing most in your life?
   • Has a movie ever shifted your perspective about how you view the world?
   • What’s the most memorable trip you’ve taken to date?
   • If you could instantly learn one skill, which would you choose?
   • What’s something that always cheers you up when you’re not having a great day?
   • What’s a fear that you’ve overcome in recent years?
   • What accomplishment makes you proud that you don’t talk about much?
   • What do you hope your life will look like five years from now?
   • What’s the most embarrassing story from your childhood?
   • What gets you most excited to get out of bed each morning?
   • Who inspires you the most in your personal life?
   • What’s a side of yourself people might be surprised to see?
   • If you could be an Olympic athlete in any sport, which would you choose?
   • What’s your favorite memory from your teenage years?
   • If you could wear any color every day of the week, what would it be?
   • How would your friends describe you?
   • What’s the perfect late-night snack?
   • What has been the happiest moment in your week so far?
   • What time of day are you most energized?
   • What's your pet peeve?

   Meet the wikiHow Experts

   Cristina Morara is a Professional Matchmaker, Dating Coach, Relationship Expert, and the Founder of a luxury matchmaking service that serves clients around the world.

   Lauren Sanders is a Professional Matchmaker and Dating Coach with over four years of experience in helping singles find love.

   Christina Stathopoulos, PCC, ACCC, is a Certified Leadership and Life Coach who specializes in leadership development, relationships, and empowerment.

   Wendy Lynne is a life and relationship coach who helps individuals break free from fear and limiting beliefs to live a fulfilling and happy life.

   April Davis is a Matchmaker and the Founder of LUMA, a high-end executive matchmaking service designed for singles seeking a long-term committed relationship.
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Section 2 of 10:

Flirty & Romantic Questions to Ask a Girl to Get to Know Her

1. 
   Make her blush by asking these flirty questions. If you're on a date, rizz her up a little with a flirtatious or romantic icebreaker. We're talking two-dogs-sharing-a-strand-of-spaghetti-until-they-accidentally-smooch romance.

   • When did you know there was something more between us?
   • What do you think makes us click so well?
   • Can you tell that you make me happy?
   • Do you think of me as a friend, or something more?
   • What’s your favorite memory of us?
   • What’s the most thoughtful gift you’ve ever received?
   • What’s the most heartwarming gesture you can imagine someone doing?
   • What fictional characters do you and I remind you of the most?
   • What’s your favorite activity to do on a date?
   • Do I make you feel special?
   • Do I remind you of any celebrities, and if so who?
   • Do you wish we spent more time together, or is it just me?
   • What does “romance” mean to you personally?
   • How do you always look so beautiful?
   • Can I do anything to make your day better?
   • What’s the most romantic moment you’ve ever had (or wish to have)?
   • What’s your favorite thing about me?
   • What do you think my favorite thing about you is?
   • If we could do anything for a date night, what would you want to do?
   • What kind of partner makes you feel safe to be your full self?
   • Do you believe in soulmates?
   • Do you sense the same chemistry between us as I do?
   • What’s your favorite thing to wear when you want to feel confident?
   • What’s your favorite kind of flirty text to receive?
   • Do you like making the first move?
   • What should I cook us for dinner?
   • What’s the nicest compliment you’ve ever received?
   • What small gestures make you feel most loved?
   • What’s something romantic you’ve always wanted to experience but haven’t yet?
   • How would you describe the way I look at you?
   • When do you feel most connected to someone emotionally?
   • When did you know you had a crush on me?
   • What’s the cheesiest pick-up line you’ve ever heard?
   • Looking for more flirty questions? Check out our forum on fun and spicy questions to ask a girl to chat with other wikiHow users!

Section 3 of 10:

Funny Questions to Ask a Girl to Get to Know Her

1. 
   Get her to crack a smile with these silly icebreakers. Your whole conversation doesn't need to be serious and deep—lighten things up a bit with a weird and goofy question like, "What's the most creative insult you've ever heard?" or "What's your favorite smell?" You might be surprised by what you can learn even by asking a funny question!

   • What is your favorite smell?
   • Have you ever gone a day without wearing underwear?
   • What is the best Wi-Fi name you have seen in your entire life?
   • Which animated fictional character do you most identify with?
   • Would you rather have feet for hands or hands for feet?
   • Have you ever fallen asleep in public?
   • What’s the sexiest name you’ve ever heard?
   • What secret conspiracy would you like to actually start letting other people know?
   • Where was the most embarrassing place you have ever farted?
   • What's the most creative insult you've ever heard?
   • Escalators or stairs?
   • Do you remember your dreams often?
   • If you had to remove one color from the color wheel, which one would it be and why?
   • If you can still remember, what are your funniest childhood memories?
   • Pancakes or waffles?
   • What’s in your favorite smoothie?
   • Silver or gold?
   • Coffee or tea?
   • Pizza or Mexican?
   • What’s an unpopular opinion that you hold about a TV show or movie that everyone else seems to love?
   • Who is your all-time favorite artist?
   • What’s a favorite food combination that other people might find odd?
   • What's the funniest thing that's ever happened to you?
   • What do you think your last words will be?
   • Who's your favorite president?
   • What has been the funniest or strangest thing that has happened to you on a first date?
   • Have you ever made a prank call?
   • What is the funniest fact you know?
   • What is it that you keep wanting to smell despite the fact that it doesn’t smell particularly good?
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Section 4 of 10:

Juicy Questions to Ask a Girl to Get to Know Her

1. 
   Get down to the nitty-gritty with some juicy and provocative questions. Questions like "What was your most embarrassing moment?" or "If your house was burning down and you could only save one item, what would it be?" will give you surprising insight into your girl's values and history and how she sees the world—plus, they're a total blast!

   • Do you keep a diary?
   • Have you ever had a crush on someone you shouldn’t have?
   • What agitates you more when you’re in a bad mood?
   • What’s the weirdest thing you’ve done in public?
   • What charitable cause are you most passionate about?
   • If your house was burning down and you could only save one item, what would it be?
   • What role would you play in defending humanity during a zombie apocalypse?
   • Have you ever been on a dating app?
   • If you won the lottery, what would you do with the money?
   • Have you ever had a crush on one of your best friends?
   • You have to date one of your friends. Who are you choosing?
   • Have you ever had a fake social media account?
   • Have you ever had a secret admirer?
   • What is your most disturbing fantasy?
   • Would you ever secretly judge someone for the amount of partners they’d had?
   • Have you ever been flat-out rejected?
   • Who is the hottest person you know?
   • What is the weirdest injury you've ever gotten?
   • What is a question you wish you were asked more often?
   • How much does your personality change when you’re around different people?
   • What’s an embarrassing thing you’ve done and never told anyone about?
   • What’s the cringiest thing you’ve ever posted on social media?
   • What’s the strangest text you’ve ever received?
   • Who was your first celebrity crush? Why?
   • Who's your current celebrity crush? Why?
   • What’s the most daring thing you’ve ever done to get someone’s attention?
   • Have you ever said something totally awkward while trying to flirt?
   • If you could change any part of your body, would you? If yes, which part and why?

Section 5 of 10:

Fun & Interesting Questions to Ask a Girl to Get to Know Her

1. 
   Try one of these out-of-the-ordinary icebreakers. Shake things up a bit by asking your girl if she believes in aliens or what the most bizarre dream she's ever had was. It'll not only tell you more about her, but it'll make the whole conversation more memorable and fun!

   • Is there a line in a movie that always gets you?
   • Do you believe in aliens?
   • What’s your favorite childhood stuffed animal’s name?
   • What’s your go-to fun fact?
   • If you could spend the night in any museum you’ve ever visited, which would it be?
   • What website can’t you live without? (She's a keeper if she says "wikiHow.")
   • Have you had any weird or unusual jobs?
   • What’s something you’ve discovered about yourself recently?
   • What’s the first thing you like doing as soon as you come home from vacation?
   • Do you collect anything?
   • If you could be any place in the world right now, where would you choose?
   • If you could go on a road trip with any celebrity, who would it be?
   • What’s something totally random that makes you irrationally happy?
   • Have you ever seen a ghost?
   • What’s always in your shopping cart at the grocery store?
   • If you could donate a million dollars to any charity, which would you pick?
   • Which fictional character do you wish you could meet in real life?
   • What’s the most random thing you know way too much about?
   • If you could only eat one meal for breakfast every day, what would it be?
   • What’s one movie that you practically have memorized?
   • If you could be born in any era, what would you choose?
   • What three things would you bring to a remote island?
   • What’s the weirdest compliment you’ve ever received?
   • What’s your biggest pet peeve?
   • If your life had a theme song right now, what would it be?
   • What’s your go-to karaoke song?
   • Which fictional universe would you love to live in?
   • What’s the most spontaneous thing you’ve ever done?
   • If you could have any superpower, what would you choose?
   • Do you have a hidden talent no one knows about?
   • What’s the best thing you’ve gotten in your mailbox recently?
   • What’s something you’ve learned on a podcast in the past few weeks?
   • Want more unique and interesting questions? Check out our forum on interesting questions to ask a girl to see what other wikiHow users have to say.
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Section 6 of 10:

Deep & Serious Questions to Ask a Girl to Get to Know Her

1. 
   These thought-provoking questions will tell you a lot about who she is. Small talk has its place, but big talk will really tell you what your crush or date values and what beliefs she holds deep down.

   • Do you have a place you’ve visited that you’d love to return to again?
   • If you could relive one day of your life, which would you choose?
   • If I gave you a beautiful picture frame right now, what would you choose to frame?
   • Is there a cause you’re passionate about?
   • Have you ever had a near-death experience?
   • Do you ever feel lonely?
   • Is there anything you’re afraid you won’t accomplish?
   • What’s your biggest fear?
   • Do you have any regrets in life?
   • What’s one thing you wish you could change about your past?
   • Do you forgive easily or tend to hold grudges?
   • What are you most grateful for right now in your life?
   • What’s the most meaningful relationship you’ve ever had?
   • Do you ever think about your beliefs and how they’ve changed over time?
   • What’s a personal motto or life motto that you live by?
   • What’s one thing you’re deeply passionate about?
   • Do you ever think about your beliefs and how they’ve changed over time?
   • What’s number one on your bucket list?
   • If you could go back and talk to your younger self, what’s one thing you’d say?
   • What’s one thing you’re most proud of accomplishing?
   • Do you have any toxic traits you’re not proud of?
   • What’s your favorite memory?
   • What would you like people to remember you for?
   • What are some difficult lessons you’ve learned from past relationships?
   • If you could describe your ideal day, what would it look like?
   • What’s something you used to believe strongly but no longer do?
   • What good has come out of a time you initially failed at something?
   • What quality do you value most in friendships?
   • Want more deep questions? Check out our forum on deep and thought-provoking questions to ask to see what other wikiHow users have to say.

Section 7 of 10:

Questions to Ask a Girl about Family

1. 
   Learn about her family of origin with these questions. A person's childhood and their relationship with their family can tell you a lot about who they are. Ask a girl these questions to understand where she came from and what role her parents and siblings (if any) play in her life.

   • What is your favorite thing about your family?
   • Are you close to your family?
   • What was your favorite childhood meal?
   • Which parent, family member or close loved one are you most similar to in terms of personality?
   • When you think of “home,” what’s the first thing that comes to mind?
   • Which TV family reminds you the most of your own?
   • If you had to cut off all communication with one of your close family members for five years, who would it be and why?
   • What’s the most immature thing your parents do?
   • What’s the weirdest tradition your family has?
   • Do you always take your parents’ advice?
   • How do you think your parents would describe you as a child?
   • Would you be willing to break the law to rescue your family member?
   • Are you close with your cousins?
   • How many cousins do you have?
   • Do you have any siblings?
   • Which three words would your family use to describe you?
   • What are the most encouraging words your parents have ever spoken to you?
   • What was the weirdest punishment your parents gave you when you were growing up?
   • How close is too close when it comes to living near your parents?
   • How many family homes have you had?
   • Who’s the quirkiest person in your family?
   • What do you love the most about your family and why?
   • What does your dad do for a living?
   • Does your family usually eat dinner together?
   • Who do you think you take most after? Your mom or your dad?
   • Can you share some of your best childhood memories with me?
   • What’s your most memorable family vacation?
   • Who are you closest to in your family? Why?
   • Does your family have any nicknames for you?
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Section 8 of 10:

Relationship Questions to Ask a Girl to Get to Know Her

1. 
   Learn more about her relationship history and expectations. It's important to ask questions that will help you understand if you're looking for the same things in a relationship and would be compatible as a couple. "Ask them what they're searching for in a relationship," advises matchmaker and dating coach Lauren Sanders. "From there, there's so many questions you could ask, it's always important to ask how they feel about children…. But [also] ask about family goals…, [and] if they want to get married, or if they just want a life partner."

   • How do you define romance?
   • What’s the most meaningful relationship you’ve had romantically?
   • Tell me about the first time you fell in love.
   • What’s a personality trait you’re working to improve?
   • Are you a jealous person?
   • What did you learn from past relationships?
   • What qualities do you look for in a partner?
   • What’s something you struggled with in a previous romantic relationship?
   • What’s your love language?
   • Is there something you don’t know about me that you want to ask?
   • What’s a deal-breaker in a relationship?
   • What constitutes a healthy relationship in your mind?
   • Do you think honesty makes a relationship stronger?
   • How will we know that our relationship is working?
   • Do you want kids?
   • Would you say you need a lot of time to yourself?
   • How long do you think people should date before getting married?
   • What are some boundaries you want to establish or maintain in our relationship?
   • What’s your biggest “green flag” in a relationship?
   • Do you ever picture yourself getting married?
   • Do you think it’s necessary that we know everything about one another’s past relationships?
   • Are you looking for a serious relationship right now?
   • How do you feel about PDA?
   • What’s the most romantic thing you’ve ever done for someone?
   • What’s the most romantic thing someone has ever done for you?
   • What’s your apology language?
   • After a fight, what makes you feel better?
   • What’s the most surprising thing about you?
   • Has love changed you in any way?

Section 9 of 10:

Questions to Ask a Girl about Goals and the Future

1. 
   Make sure you're on the same page with these questions. If you're interested in pursuing a long-term relationship with her, it helps to know if your visions of the future are compatible. Where does she see herself in 5 years? 10? Want to live in the country or the city? These types of questions will help you see if you're really compatible.

   • What is your biggest goal in life?
   • What is your dream job?
   • Would you rather have a job or a career?
   • What’s the best advice you’ve ever gotten?
   • Where do you see yourself in 5 years?
   • Do you believe in the golden rule?
   • What’s on your bucket list this year?
   • Do you live life in the fast lane or do you tend to do things at a slower pace?
   • Would you rather live in the city or the country?
   • How do you want to be remembered?
   • What’s a defining moment in your life?
   • What’s your biggest goal right now?
   • How do you define success?
   • What motivates you?
   • How do you plan to achieve your dreams?
   • What values do you appreciate in others?
   • Where do you see yourself in 20 years?
   • What do you think you'll regret later in life if you don't do? What do you think you'll regret doing?
   • What are your core values?
   • How would you describe your relationship with money?
   • Would you rather buy your dream house or travel the world?
   • Who was your role model growing up?
   • What is your idea of happiness?
   • Would you rather be rich or happy?
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Section 10 of 10:

How to Ask Questions to Get to Know Her

1. 1
   Be genuinely curious. "Curiosity is sexy," Morara notes. Asking questions is one thing, but displaying genuine interest in how she responds will help her feel like her answers really matter—and like she really matters. As matchmaker April Davis says, "Be just genuinely curious about what it is that made [her] who [she is]."

   • Davis adds: "Women want to feel seen and heard and [like] somebody understands them. [Pay] attention to those things that she's saying and [reiterate] back to her what you've heard or what one might [infer from] what she said."
   • "Notice if, when you're listening to someone, you're already planning what you want to say next, versus really listening to what they're saying," advises certified leadership and life coach Christina Stathopoulos, PCC, ACCC.
   • "I would assert [that] if you're truly present and curious in a conversation with anyone,” continues Stathopoulos, “then the next question that you ask will no [doubt] be meaningful."
   EXPERT TIP

   

   Wendy Lynne

   Life and Relationship Coach

   Wendy Lynne is a life and relationship coach based in Redmond, WA. In 2009, Wendy founded Wendy Lynne Coaching to help individuals break free from fear and limiting beliefs to live a fulfilling and happy life. With experience in relationship, career, health, and life coaching, Wendy was named a top coach by coachfoundation.com. She was trained by Martha Beck as a Life Coach and by The Life Coach School as a Master Life Coach. She is an Internal Family Systems Therapist and received advanced training in relationship coaching from the Hendricks Institute. Wendy also graduated from UCLA with a BA in Sociology and has previous experience as a Managing Director at the Mental Toughness Academy.

   

   Wendy Lynne
   Life and Relationship Coach

   People love to feel like someone is interested in them. So, instead of trying to get attention, give attention.
2. 2
   Prep some questions ahead of time. While you could make a really fun game out of taking turns scrolling this article and asking each other questions, odds are, you're not going to ask a girl 200+ questions on a first date. It can help to come prepared with a few choice icebreakers in your back pocket.

   • If possible, "Work on having your questions be the kind of question that only [she] could answer," suggests Stathopoulos.
3. 3
   Avoid pressuring her to answer questions she's not comfortable with. Obviously, some of the questions on this list are a little personal. Vulnerable and juicy questions can tell you a lot about another person, and if you and she get to the point where you're comfortable enough answering personal questions, that's great! But try not to push her to answer questions she's not comfortable with. If she declines to answer a question, gracefully move on to a less personal one.
4. 4
   Be willing to answer questions back. While it's fun to ask juicy questions to learn more about someone else, if you can't take the heat, you'd better get out of the kitchen! You should never feel compelled to answer a question you aren't comfortable with, but as a rule, only ask questions that you're willing to answer as well.
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