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50+ Fun Questions To Ask A Guy Over Text To Spark a Connection (100% Guaranteed)

Say goodbye to boring conversations and explore our list of flirty, funny questions to ask a guy over text.

Ben Bailey

Roast Founder, Dating and AI Expert

Updated January 1, 2025

Best Questions To Ask A Guy Over Text

Keeping a guy engaged over text involves asking about interests, dream destinations, and fun hypotheticals.
Spark endless conversations and deepen connections by being curious, playful, and genuine.
Make every message count with the Next Line feature. Get the best questions and prompts custom-written for you, ensuring 100% personalized and engaging conversations.

You have started liking a guy, and now you want to know them better and build a strong relationship with them. Conversation starters and pickup lines are the best way to impress your potential match, new crush, friend, or possible future partner.

The right questions can help you turn a random message into a memorable exchange of thoughts, helping you uncover common interests, quirks, and deeper layers of personality. In this article, we'll guide you through a treasure trove of thought-provoking questions to ask a guy over text.

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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.

Fun Questions To Ask A Guy Over Text

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What's the most embarrassing thing that's ever happened to you on a date?
What's the craziest thing that's ever happened to you on a vacation?
Hey, I'm curious – were you more of a Disney Channel, Nickelodeon, or Cartoon Network kid back in the day?
What's your most embarrassing moment that's so funny you can't help but laugh about it now?
What's your 'best friend' advice for conquering Monday blues?
If I were in your strangest dream, what role would I play? 😏
Can you send me the funniest picture in your phone gallery right now?
What's the craziest thing you've ever done on a dare, and would you do it again?
What's the weirdest thing you've ever binge-watched on Netflix?
What are your core beliefs about superhero preferences? Marvel or DC, and why?
What's the most epic 'out of the blue' text you've received from an ex after your last relationship ended?
Hey, I have a burning question: Netflix and chill, or prefer cuddling and laughing our hearts out?
If you ever won a million dollars, how would you spend it?
What is something that always puts you in a good mood?
What do you like to do on special occasions like birthdays, anniversaries, etc?
Tell me your favorite song.
What is your love language?
Tell me about your worst date ever – I need a good laugh!

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Flirty Questions To Ask A Guy Over Text

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How about you name some amazing stuff you'd like me to do to make you smile?
I'm trying to learn about the art of flirting. Care to demonstrate your favorite pickup line for me?
What's your dream job? I'm just curious if it involves stealing hearts and making people laugh.
Do you believe in soul mates, or should I steal your heart before someone else does?
What's your go-to meme to break the ice with a laugh? Your favorite one, please!
If I were a genie, and you were a romantic person, what would your three flirty wishes be?
On a scale from 'plain hot dog' to 'gourmet bratwurst,' how spicy do you like your flirting?
When was the first time you felt butterflies for me?
Okay, let's get cheeky with deep questions: If you could have any superpower, how would you use it to impress me?
If you could have just one wish, what would it be, besides texting me right now?
Imagine we're the last two people on Earth after a zombie apocalypse. What's our first crazy adventure together?
If you could have an entire day of fun with me, what's on your flirty agenda?
Are you a big spoon or a little spoon, and can you handle a little extra spooning tonight?
I'm curious, what's the most unexpectedly cool hidden talent you possess?
Do you believe in sharing secrets? What's your dirtiest fantasy about me?
Tell me, what's the best date idea you've ever had that's so crazy it just might work?

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Interesting Questions To Ask A Guy Over Text

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What's the most amusingly embarrassing thing you've Googled recently?
In the grand history of your past relationships, which one gave you the best nickname or inside joke?
What's your take on soul mates? And do you think they have this much fun texting?"
If we were 'best friend' travel buddies, where's the first place you'd take me and why?
What's your go-to 'funny stories' memory when you need a good laugh?
What's your biggest fear: spiders, commitment, or running out of cheesy pick-up lines?
If we were the stars of your favorite movie, what would be our epic plot twist?
What's the most interesting thing that's ever happened to you on a date?
Remember your first crush? If they were a text, what emoji would they be?
First crush reminiscing: What's the most embarrassing thing you did to get their attention?
If the zombie apocalypse struck right now, which three items in your room would you grab to survive, and why?
In a humorous twist, how would you rewrite the final chapter of our 'relationship end' story?
Night owls often have the best stories to tell. What's your most epic late-night tale?
What's your best quality – the ability to make people laugh or your irresistible charm?
What is your favorite dessert?
Tell me about your biggest accomplishment.

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Truth Or Dare Questions To Ask A Guy Over Text

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Tell me, one of your most embarrassing moments that you secretly find hilarious.
Are you a magician? Because whenever you use your favorite pickup line, you make my heart disappear.
If you had to impress me with the 'Most Useless Invention' pitch, what would you come up with to make me smile?
Meme challenge: Describe your ideal date night using only your favorite meme.
In your wildest, strangest dream, did I bring laughter or chaos? 😂
If we were in a comedy movie, and you had to do the weirdest thing to win my heart, what would that be?
Being a spiritual person, do you believe in fate bringing us together like this?
What's your absolute worst habit when no one's watching?
In a world of ordinary pick-up lines, what's the most interesting thing you'd say to make me laugh?
Speaking of deep questions, what's the most adventurous thing you've done on a whim?
What's a quirky or bizarre hidden talent you've been hiding from the world?"
Are you a night owl like me, or just an insomniac in disguise?
Tell me a funny or unusual item on your bucket list that makes you smile.
When was the last time you felt butterflies?
Alright, settle the debate: Is cereal soup, or just a cold, lazy salad?
Have you ever had a hilariously awkward first kiss experience you'd be willing to share?

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Deep Thoughtful Questions To Ask A Guy Over Text

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If you could step into someone else's life for a day, whose life would you choose, and why?
So, spill the beans: Were you the heartbreaker or the heartbroken in your past relationships?
On a scale of 1 to 10, how cringeworthy was your most embarrassing moment?
If you could have any dream job, even the outrageous ones, what would it be?
Have you come across any amusing 'funny stories' related to superstitious beliefs or urban legends that never fail to crack you up?
If you could plan a surprise date for me, what wild and wacky adventure would you choose?
What's the weirdest thing you've ever done to impress someone on a date? Spill the beans!
Tell me, what's your quirky guilty pleasure that you'd only share with someone special?
Let's play a game: Describe your favorite physical feature using only emojis. Go!
In the spirit of improvement, what's one thing you'd do differently if you could rewind to your last relationship?
What's your biggest regret in the world of fashion? Did you ever sport a cringe-worthy outfit?
What are your hidden talents, and can I expect a dazzling performance someday?
Small talk is so last season. How about we dive into the deep end? Tell me, what's your wildest dream travel destination?
If I could grant you one wish related to your dirtiest fantasy, what would it be?
What's the most unconventional thing on your bucket list that you'd never admit to anyone... except me?
Tell me your best joke.

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Conclusion

Asking questions over text is a great way to get to know a new person and build a deeper connection. Whether you are looking for a new friend or a romantic partner, asking thoughtful and interesting questions can open up the conversation and help you learn more about the person you are talking to.

Remember that it’s also important to actively listen and respond to what the other person is saying and share some personal information about yourself.

Before you leave, make sure you stand out more in the dating scene!
Put your best foot forward. Click to create the perfect icebreaker that will put you at the forefront of the dating scene. Get ready for 10x more dates!

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!