241 Questions to Ask a Guy on a Date, In-Person, or Via Text

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Did you know that a failure to ask any questions on a date is a major red flag ? Dating experts suggest that while the behavior might not be malicious, it is indicative of someone who doesn’t often pay attention to other people’s feelings. Dragging that habit into a relationship spells even more bad news. An inability to ask your partner questions creates distance. It can also complicate a pair’s ability to problem-solve. Don’t worry, though. Even if you’ve dodged the duty in the past, there are easy ways to make up for it now. All you need to do is think up a few questions and, well, ask them. And if you don’t know where to start, keep reading—especially if you’re prepping for an encounter with someone of the male variety. We’ve put together a comprehensive list of questions to ask a guy during your next night out.

READ THIS NEXT: 228 Questions to Ask a Girl During Your Next Date .

Fun Questions to Ask a Guy When Flirting

Don’t fret, the questions are coming. And it’s a good thing too because dating isn’t easy. You have to be attentive, express interest, display charm, and so many other things that may not come naturally. The worst part? You also have to keep an eye out for lulls in the conversation. If one comes, you’ve got to squash it fast. That’s where we come in. Sort through the questions below to help keep the wheels turning.

Helpful Ice-Breakers

241 Questions to Ask a Guy on a Date, In - 2

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What’s something you refuse to spend money on?
What’s your biggest guilty pleasure?
What’s your favorite holiday?
What’s your favorite movie?
Do you consider yourself a foodie?
What’s one song that you never get sick of?
What’s one musical instrument you wish you knew how to play?
Do you have a favorite author?
Do you speak any other languages?
What’s your favorite video game?
What was the last movie you saw in theaters?
What network is your favorite show on?
What’s your favorite way to relax?
What do you think has better material, Hulu or Netflix?
What’s one thing you’ve never been good at?
What’s your favorite fast food restaurant?
What’s your favorite food of all time?
What’s your mother’s name?
Where are you from?
What’s one website that you visit every day (email doesn’t count)?
Do you prefer the mountains to the ocean? Or the other way around?
What’s your favorite song?
Did you play sports as a kid?
What do you think your best quality is?
…What about your worst?
Do you prefer going out or staying in on Saturday nights?
What subject did your favorite teacher from high school teach?
Do you prefer a good movie or a good book?
Do you have any useless skills?
What food grosses you out?
Do you like old films?
Would you ever vacation in the same place twice?

READ THIS NEXT: 271 Questions to Ask Your Boyfriend Before Getting Serious .

Silly Questions to Ask Over Text

silly questions to ask a guy - couple on a date - 3

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What’s the weirdest thing on your bucket list?
What’s something you really stressed over that wound up being no big deal?
What’s one food that you could eat every day for the rest of your life?
Do you have a favorite cartoon?
Do you know how to juggle?
What’s a scene from a movie that you wish you could recreate in real life?
How many plants do you have in your apartment?
What’s the weirdest thing you’ve ever done to impress a potential love interest?
What’s the weirdest dream you’ve ever had?
What’s the best flavor combination for ice cream?
If you were granted three wishes, what would you ask for?
If you were a superhero, what kind of secret identity would you have?
What’s the best prank you ever pulled on someone?
If you had a boat, what would you name it?
Do you sleep naked?
What’s the most scandalous photo you’ve ever sent a crush?
What’s the meanest thing you’ve ever said to your parents?
What’s something you’re glad you’ll never have to do again?
What’s something that always makes you smile?
Have you ever faked it in the bedroom?
If you had to get rid of one of your five senses, which would you give up?
Do you believe in aphrodisiacs?
What was your favorite toy as a kid?
What time do you usually wake up in the morning?
If you had a catchphrase, what would it be?
What’s the weirdest thing that’s happened to you this week?
If you inherited a billion dollars, what would you buy first?
What’s your favorite pet name for a girlfriend?
Which do you like better, dogs or cats?
If you had a time machine, which era would you choose to visit?
What game show would you go on to win money?
Who would you choose to play you in a movie?
Do you have a go-to karaoke song?
Were you a boy scout?
Do you like music festivals?
What’s your most expensive hobby?
Do you know how to pick a lock?

READ THIS NEXT: 21 Questions to Ask in a New Relationship .

Funny Questions to Ask a Guy

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Which fictional character would you date?
What’s your most embarrassing moment from high school?
Who’s your favorite family member?
What’s the worst lie you’ve ever told?
What’s your weirdest habit?
Does your car have a name?
How often are you on TikTok?
Who do you think is the most handsome male actor working today?
Do you prefer being the big spoon or the little spoon?
Have you ever worn a dress in public?
Can you do any good impressions?
If asked to describe you, what’s the worst thing that your friends might say?
What’s the most embarrassing thing you’ve ever done on a first date?
Do you ever double-text?
Are you awkward around kids?
So, do you work out?
Have you ever worn make-up?
Do you snore?
Do you know the lyrics to any Broadway tunes?
Would you ever grow your hair long?
Are you afraid of birds?
What do you think about pineapple on pizza?
How many times do you snooze your alarm in the morning?
What’s one thing you wish more women understood about men?
Do you like going to brunch?
Have you ever gotten a manicure?
What’s your biggest turn-off?
What do you like most about dating?
Do you know how to change a tire?
What’s the weirdest bet you’ve ever made?
What crimes would you commit if you knew you’d never get caught?

READ THIS NEXT: 50 Cute Things to Say to Your Boyfriend Every Day .

Interesting Questions to Get to Know Someone

couple smiling at restaurant - good questions to ask a guy - 5

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What’s your dream job?
Which historical figure do you admire most?
What’s more important: being attracted to someone or being able to have an interesting conversation with them?
How old were you when you had your first kiss?
Who’s your celebrity crush?
Do you believe in aliens?
At what age do you hope to retire?
Do you like to stick to a schedule or play things by ear?
Do you prefer watching movies alone or with other people?
Do you have any pets?
What’s the most significant physical challenge you’ve ever faced?
And what’s the most significant mental challenge you’ve gotten over?
What’s something that gets you angry fast?
Do you have a favorite quote?
What’s your favorite time of year?
Are you good with computers?
Would you rather be rich or famous?
Do you want to have kids one day?
What’s one behavior that would make even the most beautiful person seem unattractive?
Are you closer to your mother or your father?
What was the last serious conversation you had with a potential love interest?
If you could only bring three items to a desert island, what would you pack?
In three sentences or less, describe your dream girl.
What’s something you would like to do for a date night?
What was one story you loved as a little kid?
What would you choose for your last meal?
What’s your earliest memory?
Do you like where you grew up?
Do you believe in the sanctity of marriage?
Do you like surprises?
How do you handle rejection?
Do you like theme parties?
What do you call your grandparents?
What’s the nicest compliment you’ve ever received?
Are you friends with any of your exes?
Do you prefer exercising alone or with a group?
What do you like to do on a day off?
Do you prefer dive bars or dance clubs?
If you had the opportunity to go back to school, what would you study?

Deep Questions to Ask

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What’s your favorite childhood memory?
Why did your last relationship end?
What’s one piece of advice you would give to your younger self?
What’s your definition of a healthy relationship?
What’s your favorite family memory?
Where do you see yourself in five years?
Is there anything that you would change about your life?
Do you consider yourself a spiritual person?
Have you ever broken someone’s heart?
What’s your biggest regret?
Do you usually make decisions with your head or with your heart?
What cultural norms do you hope to see change over the next few years?
How important is physical appearance to you?
Who’s your favorite person in the world?
What’s your love language?
Have you ever been addicted to something?
What would you never allow someone to do to you?
What’s something you’re grateful for that’s happened over the past year?
How would your behavior change if tomorrow you woke up without any fear?
What activity makes you feel most like yourself?
What motivates you to get up in the morning?
Have you ever been in love?
How has your sense of right and wrong evolved over the years?
What’s one mistake that you’ll never do again?
Have you ever been heartbroken?
How can you tell when someone is lying?
Would you marry someone outside of your faith?
What’s the most meaningful gift you’ve ever been given?
What’s something people usually get wrong about you?
Have you ever cheated on a significant other?
Have you ever been cheated on?
When do you think it’s OK to tell a lie?
What was the longest relationship you’ve ever had?
…and the shortest?
Do you think any topics are too taboo to talk about on a first date?
What was the proudest moment of your life?
If you could organize the perfect date, where would you go?
Do you believe in soulmates?
What’s your biggest phobia?
Do you consider yourself a feminist?
What’s something you would do more often if you weren’t worried about being judged for it?

READ THIS NEXT: 236 Important Questions to Ask Your Girlfriend .

Fun Questions to Ask on the First Date

couple laughing over coffee - good questions to ask a guy - 7

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What’s your favorite ice cream flavor?
Do you believe in love at first sight?
How long you have known your best friend?
Are you a morning person or a night person?
What’s your most prized possession?
What’s the funniest movie you’ve ever seen?
What’s your ideal Saturday night?
Are you a night owl?
What’s something that absolutely terrified you as a kid?
Describe a time when you really stepped out of your comfort zone.
What’s your favorite Martin Scorsese movie?
What’s your biggest turn-on?
Describe your first crush .
Do you have a favorite joke?
Do you have a favorite podcast?
Do you have any recurring dreams?
If you had the chance to be on reality television, would you take it?
If you could move to any other country, where would you go?
If you could trade lives with anyone in the world, who would you choose?
Do you like to cuddle?
In your opinion, what’s the most fun way to travel?
Do you believe in astrology?
What’s your favorite time of day?
Do you believe in past lives?
Have you ever had a fling with someone from work?
What’s the next book you want to read?
What are your favorite pizza toppings?
What do you think your most feminine quality is?
If you could learn one language with the snap of your fingers, what would it be?
What’s the best piece of dating advice you’ve ever received from a friend?
Do you believe in any superstitions?

READ THIS NEXT: 75 Relationship Quotes to Reignite Your Love .

Flirty Questions About You

Shutterstock / Dmytro Zinkevych

What’s your favorite physical feature on me?
If I were an animal what would I be?
How old do you think I was when I had my first kiss?
What’s my favorite color?
What sets me apart from other people you’ve dated?
Do you like what I’m wearing?
What’s my natural hair color?
Where are you going to take me for our second date?
Would you say that I’m your usual type?
How do you think I like my coffee?
What do you think my superpower is?
What was your first impression of me?
Do you think I’m the oldest kid in my family or the youngest?
Do I seem shy or outgoing?
Do I seem like a good driver?
What do you think my nickname was growing up?
Can you guess my middle name?
What do you think my first job was?
What do you think is my best quality?
How often do you think I date?
What do you think my bedroom looks like?
How many books do you think I’ve read over the past year?
What social media app do you think I spend the most time on?
What do you think I do for work?
How old do you think I was when I got my first job?
Do you think I’ve had a lot of boyfriends in the past?
What do you think my favorite hobby is?
What do you think I usually order at a restaurant?
What kind of cocktail should I drink?
What do you think I know most about in this world?

Wrapping Up

228 Questions to Ask a Girl During Your Next Date

man thinking of questions to ask a girl - 9

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Asking a bunch of questions isn’t just a way good way to get to know someone—it’s also an effective means of letting them know you’re interested in what they have to say. Individuals who ask a lot of questions are perceived more positively, too; appearing likable and more capable of intimacy. At the very least, the practice can lead to some great conversation. You never know when a few interesting questions will snowball into something else entirely; be it an antidote from the past or a friendly debate for new friends.

Of course, you do want to tailor things towards the person you’re speaking with, which is why we’ve compiled a list of questions to ask a girl on a first date or when trying to deepen your connection to someone close. We’ve even got a few questions that you can ask over text. Because let’s be honest—it’s not always easy to be so upfront in person. Below, you’ll find the all material you need to get started.

READ THIS NEXT: 241 Questions to Ask a Guy On a Date, In-Person, or Via Text .

228 Fun Questions to Ask a Girl

Check out the list below for new ways to strike up a fun conversation. After all, you never know when a few random questions will lead to a more interesting story. If nothing else, these prompts are sure to help you get to know each other just a little bit better.

Interesting Conversation Starters

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What’s the weirdest tradition your family practices?
What’s your favorite word in the English language?
What’s the most out-of-character thing you’ve ever done?
Do you have a favorite joke?
Who’s your favorite animated character?
What’s your dream job?
Would you rather have more money or more time?
What’s the best way to reconnect with old friends?
How did you meet your best friend?
What’s your go-to karaoke song ?
What’s your favorite movie?
What’s your favorite memory from your time spent overseas?
What’s the craziest thing you’ve ever done on vacation?
What’s the first memory you can remember?
What’s your favorite food?
Are you an early bird or a night owl?
What’s your spirit animal?
Have you ever been hypnotized?
What’s the worst job you’ve ever had?
What’s the most embarrassing phase you’ve ever gone through?
What’s the weirdest food you’ve ever tried?
What’s your favorite true crime podcast?
Do you like your name?
Who’s your favorite celebrity chef?
Would you ever take ayahuasca?
Do you have a favorite reality TV show?
What’s your favorite sport that doesn’t involve a ball?
What three words would your friends use to describe you?
Who’s your favorite fictional character?
What do you prefer, sunrise or sunset?
Have you ever been arrested?
Do you often remember your dreams?
Have you ever seen a ghost?
Would you ever pose nude for a photograph or painting?
What’s the weirdest punishment they performed during the Middle Ages?
What’s do you think is the worst quality about the opposite sex?
What’s a fun way to get to know someone, besides dinner and drinks?
What road trips would you like to take?
Would you prefer camping or glamping?
Would you rather have really nice furniture and a small house or really cheap furniture and a mansion?
What is your favorite children’s book?
Would you rather be able to play every instrument in the world or be fluent in all languages?
What’s the fanciest restaurant that you’ve ever been to and what did you order?

READ THIS NEXT: 21 Questions to Ask in a New Relationship .

Flirty Questions to Ask a Girl

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Do I look anything like your celebrity crush?
What’s your biggest guilty pleasure?
Do you like having your picture taken?
What about being a woman do you appreciate most?
What’s your favorite thing to do during a first date?
How many guys have performed a grand romantic gesture for you?
What’s the stupidest thing someone has ever said to you on a first date?
What do you think my body language is trying to tell you?
What do you usually wear to bed?
Have you ever purchased something from an adult retailer?
Where do you like to be kissed most?
What’s your favorite part of the male body?
What do you think the most beautiful part of the female body is?
When am I taking you out to dinner?
Do you believe in love at first sight?
What’s your biggest turn-on?
Have you ever filmed yourself getting it on?
What are the top three qualities you look for in a partner?
Do you prefer to make the first move?
Have you ever sent a dirty text message?
Do you prefer kissing or cuddling?
Did you ever have the hots for a teacher?
What color do you think would look best on me?
Where would you rather meet up, a cafe or a bar?
How would you describe your ideal relationship?
What’s more important, intelligence or appearance?
What are your biggest turn-offs?
How many dates would you need to go on before engaging in a Netflix and chill?
Do you have any secret talents?
Do you like trying new things?
Have you ever gone skinny dipping?
Do you like massages?
What’s your favorite way to relax?
Do you have plans this weekend?
Ideally, how long would intimacy last?
Have you ever initiated a booty call?

READ THIS NEXT: 271 Questions to Ask Your Boyfriend Before Getting Serious .

Funny Questions to Ask a Girl

women laughing and flirting with one another - 12

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What’s your most embarrassing moment?
What’s the weirdest thing that’s ever happened to you on a date?
What’s the best practical joke someone has ever pulled on you?
What’s the worst pick-up line someone has ever used on you?
How would you defend yourself during a zombie apocalypse?
What’s an irrational fear that you can make some sense of?
Which U.S. president would make the best boyfriend?
What kind of food do you think is totally disgusting?
Who is the least talented actor working today?
What’s your Hogwarts House?
Have you ever lied about your age?
Have you ever participated in a hot dog eating contest?
Would you care if your boyfriend had a more elaborate skincare routine than you?
Do you have a favorite dinosaur?
Would you rather be allergic to the sun or allergic to your favorite food?
What’s the funniest thing you’ve ever overheard?
When was the last time you sent something via snail mail?
What was your favorite TV show as a kid?
What’s your biggest pet peeve?
What’s one habit that you’ve carried with you since childhood?
Pineapple on pizza: yes or no?
Would you rather have a private plane or a private yacht?
What’s your favorite condiment?
What fictional character do you think would be easiest to beat in a fight?
How would you defend yourself during the Purge?
Which color do you think would taste the best?
If you were an instrument what would you be?
What’s one body part do you think you could live without?
Which cartoon character do you think is most likely to be a serial killer?
Which founding father would make the best sugar daddy?
What’s the sexiest fruit you can think of?
What’s the worst bathroom experience you’ve ever had?
How would you react if you found a rodent in your bedroom?
What type of cheese matches your personality best?
What’s your favorite writing utensil?
What show are you currently binge-watching?
Have you ever cross-dressed?
Do you know how to set a table properly?
What’s your favorite cheesy quote?
Whose clothes would you prefer to wear, your mom’s or your dad’s?
Do you still watch any cartoons?
If you had to join the circus, what job would you want?
Would you rather live in a world full of witches or a world full of superheroes?
Let’s say reincarnation is real: What would you want to come back as?

READ THIS NEXT: 50 Cute Things to Say to Your Boyfriend Every Day .

What If Questions to Ask a Girl

man thinking of questions to ask a girl on their date - 13

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What if you only had one day left to live? What would you want to do?
What if you could relive one day in your life? Which would you choose and why?
What if you could go back in time and change the future of events? Would you do it?
What if you could read people’s minds? Would you use your superpower for your own personal gain?
What if your family didn’t approve of your significant other? Would you still stay with them?
What if you had to decide between love and money? What would you choose?
What if we got stranded in a remote location? Who do you think would save the day?
What if you met a guy who didn’t speak English? Would you give him a shot?
What if you were given one million dollars? What would you buy first?
What if you had to decide between your vision and your hearing? Which sense would you choose to keep?
What if someone you love committed a terrible crime? Would you visit them in prison?
What if you could live for 200 years? Would you do it?
What if you could cure a disease? Which one would you choose to eradicate?
What if you could experience happiness without any sadness? Would you choose to forgo the latter?
What if you were invited to have tea with the King of England? Would you accept the offer?
What if you could learn a new language with the press of a button? Which one would you choose?
What if you could get away with never doing a certain chore ever again? Which one would you avoid?
What if you became President of the United States? Which cause would you pursue first?
What if you could teleport anywhere in the world? Where would you go?
What if one of my friends made a move on you? Would you let me know?
What if you found out the guy you were dating liked dancing naked to the Backstreet Boys? Would that be a dealbreaker?
What if your boyfriend went to prison? Would you wait for him?
What if I gained a ton of weight? Would you still be interested in me?
What if your worst fear came true? How would you cope?
What if animals could talk? Which would be most annoying to listen to?
What if you weren’t allowed near a computer for the next month? Would you catch up on your reading or simply move operations onto your phone?
What if you could only watch one reality TV show for the rest of your life? Which would you choose?
What if you could only communicate by breaking out into song? Which one would you choose to let people know you were upset?
What if you could play the perfect prank? Who would you target?
What if real life were more like the movies? Which film would you want yours to resemble?
What if your 13-year-old self drafted your dating profile ? What would it say?
What if you went on a first date with someone who only listened to elevator music? Would you agree to go out with them again?
What if you could pick a famous person to insult? Who would you choose and what would you say?
What if you had to eat the same meal every day for the rest of your life? What would you make?
What if you had to choose a different hair color? Which would you settle on?
What if animals could make documentaries about humans? What weird things would they show?
What if you were born a child prodigy? What skill would you want to excel at?

READ THIS NEXT: 236 Important Questions to Ask Your Girlfriend .

Questions to Ask a Girl Over Text

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Shutterstock / Tero Vesalainen

Are you watching anything good right now?
What’s the most annoying thing about where you live?
Have you already had dinner?
How do you feel about small talk?
What’s your favorite emoji?
What’s a GIF that best describes how you’re feeling right now?
How’s work going?
What are you wearing?
What’s the funniest thing you’ve seen on TikTok today?
What are your plans for this weekend?
What’s your favorite place to get takeout from?
What’s the cutest thing your dog/cat has done today?
Is it cold in your apartment/house right now?
Have you had coffee yet?
What are you doing for dinner?
What’s your favorite quote from a movie?
What time are you going to bed?
What’s a song that you can listen to over and over again?
What’s the weirdest message someone has ever sent you on Tinder?
What’s the funniest picture you have on your phone?
Which phone app do you use most?
What’s the weirdest thing that’s happened to you this week?
What do you usually do on the weekends?
Do you want to FaceTime?
Are you watching anything good tonight?
Do you have a favorite documentary?
Will you send me a picture? It can be of anything!

READ THIS NEXT: 50 Cute Things to Say to Your Girlfriend Every Day .

Deep Questions to Ask a Girl

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Shutterstock / adriaticfoto

What’s the biggest lesson life has ever taught you?
Do you consider yourself a spiritual person?
What do you think is the worst thing about getting older?
What’s one activity that you have on your bucket list?
What’s your favorite childhood memory?
Who is your favorite family member?
Have you ever been in a long-distance relationship ?
What personality trait do you consider to be a red flag?
What types of jobs exist only because people are lazy?
Do you consider yourself to be a good person?
Have you ever confronted any of your deepest fears?
What’s one thing you would want both you and your significant other to enjoy?
Is there anything you would change about yourself?
What do you think is the most dangerous quality a person can possess?
Do you have a good relationship with your mom?
What are three principles you want to instill in your children?
What energizes you?
What’s your worst habit?
If you could be a fly on the wall anywhere and at any point in history, what would you choose and why?
What do you want to be remembered for?
Do you want to get married someday?
If you wanted children, but couldn’t conceive naturally, what other options would you consider?
What’s something you want to achieve in life?
When are you happiest?
If you won the lottery, would you still want to work?
What sounds more appealing, stability or spontaneity?
How can you tell when you’re in love?
Who do you call when you need advice?
Would you take in a stray animal that needed a home?
What’s the best compliment you’ve ever received?
What smell brings you comfort?
How would you like to be perceived by others?
Do you keep in touch with your exes?
When you enter a room, do you prefer to stand out or blend in?
Would you prefer to live in a treehouse in the woods or a cottage by the ocean?
Would you rather be known for your beauty or kindness?
What’s the most important thing for a healthy relationship?
What single event has had the biggest impact on who you are?
What’s the most extreme example of poverty you’ve ever seen?
Do you think that war is inevitable or that specific leadership styles can help us avoid it?
Do you believe in past lives?

241 Questions to Ask a Guy on a Date, In-Person, or Via Text#

Fun Questions to Ask a Guy When Flirting#

Helpful Ice-Breakers#

Silly Questions to Ask Over Text#

Funny Questions to Ask a Guy#

Interesting Questions to Get to Know Someone#

Deep Questions to Ask#

Fun Questions to Ask on the First Date#

Flirty Questions About You#

Wrapping Up#

228 Questions to Ask a Girl During Your Next Date#

228 Fun Questions to Ask a Girl#

Interesting Conversation Starters#

Flirty Questions to Ask a Girl#

Funny Questions to Ask a Girl#

What If Questions to Ask a Girl#

Questions to Ask a Girl Over Text#

Deep Questions to Ask a Girl#