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50+ Clever, Funny Questions To Ask A Girl Over Text To Break The Ice (100% Guaranteed)

Connecting with your favorite girl starts with asking the right questions. So, bring out your flirty, funny side with these conversation starters to bring a big bright smile to her face.

Ben Bailey

Roast Founder, Dating and AI Expert

Updated January 1, 2025

Best Questions To Ask A Girl Over Text

Engage a girl in interesting text conversations by inquiring about her dreams, desires, and funny anecdotes.
Build a deep and meaningful connection with open-ended questions that show genuine interest.
Make the first impression count with a captivating opener. Craft your perfect text now, with our Next Line feature.

Girls love someone who can make them laugh and make them feel special. If you are ready to impress your special girl, then it's time to prepare some interesting, funny questions to ask a girl over text. Right conversation starters help you create a delicate balance – where you neither come across as overly eager or intrusive nor do you look too casual or disinterested.

It's essential to let your fun and flirty side shine to win her over, making her realize you're the one she's been waiting for. If you're unsure where to begin, here are a few questions to ask a girl over text, helping you express your genuine interest and affection without creating an awkward situation.

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Table of Contents

Here is the outline of the article, feel free to jump to the section that interests you the most.

Personal Questions To Ask A Girl Over Text:

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In the world of strange dreams, what's the most bizarre dream date you can imagine?
Tell me about an embarrassing thing that you secretly enjoy doing or talking about.
What's your favorite TV show for a Netflix and chill night? Any recommendations?
What do you think how would your friends describe you to me?
What's the most interesting question someone has ever asked you?
What do you like to do in your free time?
If emojis could define your current relationship status, which one best represents your connection with humor – 😂, 😊, or 😅?
Between a morning person and a night owl, who do you think has a better sense of humor, especially when it comes to flirting?
What's one bad habit that you secretly enjoy?
If I were to surprise you with your dream date tomorrow, what's the one thing you'd want me to include or know about it? Spill the dream date secrets!
What's the weirdest thing you've ever binge-watched on Netflix? Any guilty pleasures?
Coffee date attire: Casual and comfy or dressed to impress?

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Deep Questions To Ask A Girl Over Text:

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If you could erase one embarrassing thing from your past, what would it be, and why?
If a bizarre dream were to come true, what's the one adventurous thing you'd do?
Who would you say is the most influential person in your life?
What's your ultimate 'opposite sex' superpower fantasy?
If you ever won a million dollars, how do you plan on spending them?
Which of your favorite movies describes our current relationship status the best?
What's the one thing your dream guy must absolutely know about you to win your heart?
Let's talk about firsts: Who was your first teacher crush, and what subject did they teach?
What act of kindness gave you the most satisfaction?
If our lives were a reality TV series, what would be the tagline in the opening credits that describes our dynamic?
What's a guilty pleasure of yours that you think would surprise me?
If you could have a superpower like a cartoon character, what would it be, and how would you use it in your everyday life?

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Interesting Questions To Ask A Girl Over Text:

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I'm curious, what's your dream job, and would it involve wearing a cape?
What's the most healthiest and unhealthiest thing you can't live without?
What's your all-time favorite movie that you could watch on repeat, and why?
What's the craziest thing you've ever done on a dare?
What is our current relationship status?
In your opinion what is the great conversation starter to break the ice?
What's your most lovable biggest character flaw that I should know about?
What's your all-time favorite song that never fails to make you smile?
What's your idea of a picture-perfect date?
What's the funniest or most embarrassing thing you learned about yourself in your former relationship?
Here's a fun yet interesting question: If you had to teach a class on a subject you're passionate about, what would it be, and why should I enroll?
What's the biggest fashion faux pas you've ever committed? Spill the stylish beans!
What's your most amusing 'broken someone's heart' story, if you have one?

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Hilarious And Funny Questions To Ask A Girl Over Text:

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What's your most embarrassing moment that still makes you laugh?
If 'too much money' magically appeared in your bank account, what's the first thing you'd do to make the world a better place?
If I were to use the cheesiest pick-up line on you, would you still talk to me?
What's your biggest fear: Spiders, or me telling more dad jokes?
In a parallel universe where we're having a deep conversation with penguins, what's our topic of discussion?
Let's break the ice with humor: What's the worst pickup line you can come up with right now? I promise not to judge too harshly! 😁
Share the weirdest thing on your bucket list. I promise not to judge!
In a karaoke battle, would you prefer singing a cheesy '80s love song or a modern pop hit to win someone's heart?
If you get a chance, What one personal question you would love to ask your favorite celebrity?
What one funny question you would ask your crush to make them smile?
What's the most annoying thing you secretly love about someone you've dated in the past?
What's the most important lesson you've learned from your dating experiences? And don't say, 'Avoiding guys who ask cheesy questions.' 😉

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Flirty Questions To Ask A Girl Over Text:

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Let's dive into some flirty fun: If you could grab someone's attention with a clever pickup line, what witty words would you use to make them smile?
If you had to give the most useless advice to someone, what would it be, and can you use it to flirt with me?
They say 'dating daddy's girl' is the best at balancing sweetness and sass. Can you prove it with a flirty question?
Flirty Questions time: What's your favorite cheesy pickup line, and has it ever worked on you?"
Imagine we're in a 'useless advice' competition. What's your pro tip for making a girl smile?
Do you believe in love in the first text, or should we keep digging for a 'deeper conversation'?
If you had to use the worst pickup line on me, what would it be? 🙈
On a scale of 'Last Christmas' to 'All I Want for Christmas Is You,' how much do you look forward to seeing me again?
If you were to have a 'guilty pleasure day' where you could do anything you wanted, what would it look like?
What's more important good sense of style or a good sense of humor?
If you had to describe yourself in one word, what would it be, and why?
In just one word, describe the kind of kiss that gives you butterflies.

The Perfect Icebreaker Is Just a Click Away

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Romantic Questions To Ask A Girl Over Text:

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If you could go on a date with any fictional character, who would it be and why?
What's the most unexpectedly romantic thing someone has ever done for you?
What's the most daring item on your personal bucket list, and can I join you in checking it off?
If we are stuck on a desert island, what's your idea of the perfect romantic evening under the stars?
If you were given a million dollars right now, where would our dream date take place?
If we were to star in one romantic movie, what would the title be, and who would play our leading roles?
Hey there, what's your biggest character flaw that would make you a villain in a rom-com?
If we ever have to write a quirky 'future reference' manual for our relationship, what should be the first chapter title?
In your idea of the perfect romantic evening, would we be stargazing or having an epic dance-off under the moonlight?
If our romantic relationship were a book, what would be the story's first line about us?
On our first date, would you go for an epic dessert or a crazy adventure activity?
Do you believe in the saying that love makes us better people? What's your take on it?

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Conclusion

In the world of text messaging, asking deep and funny questions to build an interesting conversation can be a delightful way to get to know a girl over text.

By weaving humor into conversations about matters of the heart, you keep things light and create a memorable connection. So, go ahead and use these interesting questions to ask a girl over text to start a conversation and make your text chats with that special someone both meaningful and amusing.

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Ben Bailey

Ben is one of the best Dating Experts I've ever met and one of the few that cracked the algorithm of online dating. Every week, Ben is publishing new articles on ROAST, helping 20M+ of people to get more matches, dates, and find the one!