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250 Best First Date Questions To Ask A Guy Or A Girl

I still remember my first real date. You know, the first one where we both knew it was a date.

I sat across from her nervously clutching a sweating glass of soda, heart racing as if I’d sprinted a mile. I wanted to come off cool, confident, interesting…but drawing a blank.

Then I asked her the first question that popped to mind that felt remotely human.

“What made you say yes to coming out with me?”

She laughed. Not nervously—too embarrassed to laugh. She laughed with warmth, surprise. That broke the seal. We talked. I asked her question after question.

The magic wasn’t in being clever. It was in being curious. Each question brought us closer. Made us smile more. Barely a single sentence answered before another question was asked.

Ever since that night, I realized something unforgettable:

first dates aren’t about impressing someone. They’re about opening them up.

First dates are thrilling…terrifying.

You’re sitting across someone new, trying desperately not to appear like a nervous mess on the inside. You know all those late night thoughts screaming in your mind:

What do I say? !

Talking to someone new is weird no matter who you are. We’ve all been there.

You don’t want the date to feel like an interview. You don’t want to share too much too soon. hell — you don’t even just want to sit there in silence staring into your drink.

You want conversation to flow.

To be natural. Easy.

Questions are the key.

Good first date questions aren’t about wowing someone. They’re about exploring & discovering. About learning personality, values, humor, and chemistry. About uncovering if the person across from you is actually someone you want to spend more time getting to know.

You don’t need to ask all (or even most) of them. Just feel into the ones that fit and enjoy being present.

Enjoy getting to know someone.

250 Best First Date Questions To Ask A Guy Or A Girl

Icebreakers 

• What made you say yes to this date?

• How’s your day been so far?

• Morning person or night owl?

• What’s your comfort food?

• What’s something that always makes you laugh?

• Coffee or dinner dates?

• What do you like to do on weekends?

• What’s the last show you watched?

• What’s your favorite season?

• Introvert or extrovert?

• What’s your favorite drink to order?

• Tell me a random fact about you.

• What’s your favorite spot in the city?

• Spontaneous or planner?

• What’s something small that makes your day?

• What’s your favorite dessert?

• What kind of music have you been listening to lately?

• What’s the best meal you’ve ever had?

• How do you like to relax?

• Beach or mountains?

• If you could celebrate any holiday every year, what would it be?

• Texter or caller?

• What’s your favorite smell?

• What’s something you’re excited about?

• What does your perfect day look like?

Related: 180 Truth Or Dare Questions For A Date

Fun & Lighthearted 

• If you could become amazing at something overnight, what would it be?

• What’s the weirdest food you’ve ever eaten?

• What’s your guilty pleasure show?

• Would you rather travel to the past or future?

• What was your favorite cartoon as a kid?

• What song do you hate to love sing karaoke?

• If you won a free vacation tomorrow, where would you go?

• What’s your favorite flavor of ice cream?

• Do you believe in astrology?

• What’s your spirit animal?

• What’s your favorite movie of all time?

• What’s the most random talent you have?

• Dogs or cats?

• What’s your favorite board game or card game?

• Tell me about the last impulsive decision you made that actually worked out.

• What’s your favorite memory from childhood?

• If you could eat one thing for the rest of your life, what would it be?

• Do you like getting surprises?

• What was the last thing that made you happy?

• How do you like to celebrate your birthday?

• What’s your favorite emoji and why?

• If you could live anywhere in the world, where would you live?

• What’s your favorite type of weather?

• What’s your favorite snack?

• Do you believe in love at first sight?

Related; 90 Truth Or Dare Questions For Kids

Personality & Values 

• What do you look for most in others?

• What do you feel proudest of?

• What inspires you when you’re feeling stuck?

• What does life look like when you’re living your best life?

• How do you cope with stress?

• Tell me about something you’re working on.

• What was a lesson life taught you too early?

• What activities make you lose track of time?

• How do you define success?

• What’s something you’ll never allow someone to take away from you?

• What types of people do you look up to?

• How do you recover after an emotional rollercoaster?

• What qualities are you looking for in a partner?

• How do you show others that you care?

• If you could tell the world one thing about you, what would it be?

• What do you feel is your biggest strength?

• What bad habit are you trying to break?

• How do you like to feel appreciated?

• If home were a feeling what would it be?

• What was the last thing that you felt grateful for?

• How do you resolve arguments with others?

• What’s something you’re afraid of?

• What do you feel you don’t have enough of?

• How do you relax?

• What book changed your perspective on life?

Related: 150 Truth Or Dare Questions For Teenagers

Dating & Relationships 

• How would you describe a healthy relationship?

• How do you like to receive affection?

• What’s one thing you learned from your last relationship?

• What do you look for in a partner?

• How do you give compliments?

• What’s a complete dealbreaker for you?

• How do you feel emotionally safe with someone?

• How do you show love to others?

• How important is communication to you in a relationship?

• If you could ask the universe one question about love what would it be?

• How do you deal with jealousy?

• What do you need from your partner?

• What was your best date ever?

• Tell me about your goals for future relationships.

• How do you know when you’ve connected with someone?

• What are you willing to commit to someone?

• If your partner did something that hurt your feelings how would you want them to approach the situation?

• What do you admire about your favorite couple?

• What’s your biggest turn on?

• Describe a type of person you lose interest in quickly.

• If you could tell your partner one thing about your future together what would it be?

• How do you give someone the butterflies?

• What does love mean to you?

• What are you looking for on your next relationship?

• How do you know when someone is unforgettable?

Related: 50 Questions to Improve Emotional Intimacy in Your Relationship

Life Goals & Dreams 

• Share with me a dream that no one knows.

• If you could wake up tomorrow and have everything you wanted in life what would it look like?

• What’s something you still want to check off your bucket list?

• What is your biggest goal in life?

• What’s something you’ve always wanted to learn?

• Tell me about a goal that you’re working towards.

• If you could wave a magic wand and life your best life what would it look like?

• What did you want to be when you grew up?

• How do you want to impact the world?

• Where want to travel to that you’ve never been before?

• What about the future excites you?

• Share with me one item on your bucket list.

• If you could achieve anything in life right now what would it be?

• What would you do if you knew you couldn’t fail?

• What’s something you hope to reach in the next few years?

• If you could bottle up life fulfillment, what would it smell like?

• What do you want to create?

• Tell me about a goal that you already reached that you’re proud of.

• If you could describe your life with one word or phrase what would it?

• What movies you watch on repeat that keep you motivated to live your best life?

• If you could live your best life tomorrow what would that look like to you?

• What drives you to be the best version of yourself?

• How would you describe true happiness?

• If you could wake up tomorrow feeling _____ every day, what would you want to feel?

• What would make life worth living for you?

• If you could live your perfect life what would you be doing?

Childhood & Background 

• Where are you originally from?

• How would you describe your childhood?

• What kind of kid were you?

• Who were your biggest influencers growing up?

• What’s something that happened to you as a kid that still makes you smile?

• What did you want to be when you grew up?

• What did your family teach you growing up?

• How would you describe the relationship you have with your family?

• What’s your favorite family tradition?

• What’s your favorite meal that your parents used to make you as a kid?

• What did you love to learn about in school?

• Sports team fan?

• Tell me about yourself as a kid.

• What’s something you miss about being young?

• Who was your idol growing up?

• What was the best lesson you learned as a kid?

• What did your weekends look like?

• What fear did you overcome from when you were little?

• What event from your childhood helped shape who you are today?

• What’s your favorite story your parents tell about you as a kid?

• What value did your parents raise you with that you still live by today?

• What’s your favorite memory from your childhood?

• What’s something that used to make you really happy as a kid?

• What scars do you have from childhood that you’ve learned from?

• What was something your family would always do?

• How did you feel growing up about the home you lived in?

Deep & Thoughtful 

• What is your purpose in life?

• If you could tell your younger self one thing what would it be?

• How would you describe inner peace?

• What do you think you’re here to heal?

• What’s something you wish someone told you when you were younger?

• What scares you about letting someone else get too close to you?

• What makes life meaningful?

• How would you define emotional intimacy?

• What’s something you struggle with internally?

• How do you define freedom?

• What lessons are you currently learning about yourself?

• What belief do you hold about yourself that you know is no longer true?

• What are you grateful for?

• What questions do you have for yourself right now?

• Who do you feel understands you the most?

• How would you define love?

• What are you wanting to improve on emotionally?

• How do you grow within yourself?

• What experience changed your life?

• If you could ask the universe one question about emotional intelligence what would it be?

• How would you define feeling seen?

• What hardships have you overcome that you’re proud of?

• What words do you live by?

• What regrets, if any, do you have in life?

• What are you willing to let go of to allow happiness into your life?

• How do you find meaning in life?

Travel & Adventure 

• Where’s your favorite place you’ve visited?

• If you could visit one place for the rest of your life what would it be?

• Road trips or flying?

• lone traveller or tour group?

• What’s the most beautiful place you’ve ever seen?

• What’s your favorite city?

• What’s the best trip you’ve taken?

• If you could go on the vacation of your dreams where would you go?

• What type of traveler are you?

• What country have you always wanted to visit?

• What’s your favorite travel memory?

• Would you rather travel with someone or by yourself?

• What types of adventures do you love?

• What new experience do you wanna try?

• What’s your favorite thing to eat on the road?

• If you could only drive to one spot for vacation where would you go?

• What’s the furthest place you’ve traveled?

• Where’s somewhere that gives you magical vibes?

• What’s one place on your travel bucket list?

• If you could go anywhere for your honeymoon where would you go?

• Would you rather be surrounded by cities or nature?

• If you could pick anywhere in the world to live that felt like home where would you live?

• Where’s the next place you’d like to visit?

• Are you more of a backpacker or luxury trip kind of person?

• If you were planning the perfect adventure with someone, where would you take them?

Flirty & Playful 

• What do people find attractive about you?

• What do other people love about you when it comes to relationships?

• What’s your biggest accessory?

• If your brain and body weren’t scared, what would you do?

• If you could tell your body one thing what would it be?

• What’s your ideal date?

• What touches your soul?

• What type of compliments do you enjoy?

• What’s your sensitive side like?

• How do you like to flirt?

• What are you good at that no one would expect?

• If you could describe the ideal chemistry, what would it be like?

• How would you describe someone that you’ll never forget?

• When you walk into a room what type of energy do you bring?

• What can I do to catch your attention?

• How do you like for someone to look at you?

• How do you like being touched?

• What type of attention are you into?

• What do you enjoy about dating?

• If a guy told you he enjoyed every moment with you what would you think?

• What does your type like to hear?

• If I smiled at you from across the room what would you think?

• What type of relationship are you looking for?

• What turns you on?

• How do you take compliments?

• What’s your kryptonite?

Wrap-Up & Connection 

• Tell me something about you that I should know.

• What was the highlight of your day?

• What did you not expect about me?

• What are you looking forward to right now?

• Tell me about the type of connection you want.

• If we ended up going on a second date what would you want to do?

• What would you want me to know about spending time with you?

• What gives you hope about dating right now?

• What are you willing to explore?

• Did you have any expectations entering this date? If so, what were they?

• What matters to you at this moment?

• What type of future do you want with someone?

• How do you know when you feel connected to someone?

• What do you appreciate about spending time with others?

• What adventures bring you back to life?

• Tell me about the partner you want to be for me.

• How does happiness with another person look like to you?

• If you could experience one thing with someone what would it be?

• If you could feel one way every day what would you want to feel?

• Why do you want to connect with me?

• What type of love do you believe in?

• What’s one thing you hope for in your life?

Final Thought

You don’t have to memorize these questions.

Let the conversation flow. Don’t force it.

The secret to the best dates isn’t trying to make sure you’re witty and smart. It’s showing up as yourself and being curious to learn more about someone else.

As always…

enjoy the conversation!

ONWE DAMIAN
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