This article was written by Suzanna Mathews
and by wikiHow staff writer, Aly Rusciano
. Suzanna Mathews is a Dating and Relationship Coach and the Founder of The Date Maven. With over a decade of experience, she specializes in creating mindset tools, social strategies, and digital strategies that help her clients elevate dating and deepen connections. Suzanna holds a BA in Communications from Bethel College, North Newton, and an MA in Theater and Dramatic Arts from Wichita State University.
This article has been fact-checked, ensuring the accuracy of any cited facts and confirming the authority of its sources.
This article has been viewed 27,655 times.
You want to talk to your crush or boyfriend, but how do you do that when you get lost in those handsome eyes? Well, worry not because we’re here to help! We’ve compiled a list of the best flirty questions you can ask a guy (in person or over text) to start and keep the conversation going. Try these out on a first date, in the bedroom, or while you’re hanging out to say, “Hey, I’m into you.”
This article is based on an interview with our dating and relationship coach, Suzanna Mathews, founder of The Date Maven. Check out the full interview here.
Steps
Cute
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1What color do you think I look best in?
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2What’s your favorite part of the day?Advertisement
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3What was your first impression of me?
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4What’s your idea of a perfect weekend?
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5What’s something that always makes you smile?
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6What’s something many people don’t know about you?
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7What makes you laugh?
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8Who’s the first person you call when something good happens?
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9If I was a flower, what type of flower would I be?
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10What do you think my favorite food is?
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11What are 3 things on your bucket list?
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12How do you like to relax after a long day?
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13What’s the best compliment you could receive?
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14Do you like surprises?
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15What’s something you could never live without?
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16What do you think is the best part about being in a relationship?
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17You can only pick one: sunsets or sunrises?
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18What makes you happy?
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19What meal would you cook to impress me?
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20What are you thinking about?
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21What’s your favorite thing about me?
Fun
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1What’s a song that describes us?
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2If you could go anywhere in the world, where would you go?
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3If you were an animal, what would you be?
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4Who’s your favorite fictional couple?
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5What’s the best song of all time?
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6What movie would you live in?
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7If you could master any skill, what would it be?
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8If you were a dessert, what would you be?
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9What’s your favorite ice cream flavor?
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10What’s the spiciest food you’ve ever had?
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11If you were famous, what would you be famous for?
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12What’s your favorite board game?
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13What are you most afraid of?
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14You can only pick one: love or money?
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15What’s your worst nightmare?
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16What would you do if you won the lottery?
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17If you had 3 wishes, what would they be?
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18When was the last time you laughed so hard you cried?
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19If you were a superhero, what would your power be?
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20Who’s your celebrity crush?
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21What’s one food you can’t live without?
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22Are you a homebody or an explorer?
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23Have you ever gone skinny dipping?
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24What’s your favorite tear-jerking moment in a movie?
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25What’s your favorite book?
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26What would you do if you won the lottery?
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27What’s your ideal meal?
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28What was the last show you binge-watched?
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29What’s your go-to karaoke song?
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30Do you think aliens exist?
Romantic
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1What’s your love language?
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2What’s your idea of a perfect date?
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3What does love mean to you?
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4Do you prefer hugging or kissing?
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5Do you prefer movie or restaurant dates?
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6Do you believe in love at first sight?
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7Where would you take someone on a first date?
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8Would you consider yourself a romantic?
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9In your opinion, what’s the worst pickup line?
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10What does your ideal relationship look like?
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11Do you believe in soul mates?
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12Would you rather go on a romantic getaway or Netflix and chill?
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13When was your first kiss?
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14Have you ever dreamed about me?
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15Do you think I’m a good kisser?
Spicy
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1How do you picture me at night?
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2What’s your biggest turn-on?
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3What’s one thing you’ve always wanted to try in the bedroom?
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4What would you do if I answered the door naked?
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5Lights on or off?
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6Do you have a secret fantasy?
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7What are your 3 favorite body parts?
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8What do you wear to bed?
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9Do you think about me when you’re alone?
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10Are you into giving or receiving?
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11Do you like massages?
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12Do you have a guilty pleasure?
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13Are you a big spoon or a little spoon?
Deep
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1What does success look like to you?
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2What traits do you think are the most important?
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3Have you ever had your heart broken?
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4What’s something you regret?
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5What’s the nicest thing someone’s done for you?
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6Who do you look up to?
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7Have you ever been in love?
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8What do you admire most about your life?
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9What’s an accomplishment you’re proud of?
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10What’s your dream job?
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11If you could change one thing about yourself, what would you change?
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12What would you change about social media?
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13What’s your biggest fear?
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14What’s the best gift you’ve ever gotten?
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15What makes you angry?
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16If you could go back in time and change one thing, what would you change?
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17How would your friends describe you?
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18What’s your favorite childhood memory?
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19Are you an introvert or an extrovert?
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20What do you admire most in people?
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21Do you believe in second chances?
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22What are you the most grateful for?
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23What’s the most spontaneous thing you’ve ever done?
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24What’s the biggest lesson you’ve learned?
Silly
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1What meme best describes your life?
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2Would you rather share your internet search history or bank balance?
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3If you came with a warning label, what would it say?
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4Would you rather be a high school teacher or a clown?
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5What’s the sexiest vegetable?
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6If you were president, what would you do first?
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7Would you rather only speak in rhyme or sing every time you speak?
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8Is a hot dog a sandwich?
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9What’s one sound that describes you?
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10Would you rather be itchy all the time or have constant hiccups?
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11If you were a ghost, what would you haunt?
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12What alias would you use if you were a spy?
Expert Q&A
Tips
- The best way to flirt with a guy is to be playful and have fun! So, don’t be afraid to tell a few flirtatious jokes to make him smile.Thanks
- Ask about a guy’s interests and passions to see what you have in common and spark a deeper conversation .Thanks
- Use these questions as conversation starters in person or over text—they work just the same!Thanks