Inspiring meaningful connections & fun, happy lives...


Join Our Newsletter


120 Questions to Ask a Guy Over Text

The best questions to ask a guy over text are those that are fun. You can be flirty and playful and before you know it, you have some great insights!   


It’s fun because it is the perfect way to find out so much more about him since we tend to tell stories while answering questions. And those conversations are what leads to deeper connections between you both.


Questions to ask a guy over text


  1. What do you notice first when you see a woman?


  1. Who are you closest to at work?


  1. Would you rather work at home or at the office?


  1. What was the craziest thing that has happened to you since the pandemic started?


  1. Do you think people will change after the pandemic is over? In what ways?


  1. When is your next planned vacation?


  1. What is your biggest motivation?


  1. Do you like or are you good at fixing things?


  1. Do you enjoy working in the yard or growing things?


  1. What is a favorite memory of your grandparents?


  1. Are you a procrastinator?


  1. What do you always look forward to doing?


  1. What is your go-to quick bite to eat?


  1. Would you rather Chinese for Italian food?


  1. What is your favorite sport to play at family get togethers?


  1. What family food do you look forward to during the holidays?


  1. Does your family have something that they are “known” for?


  1. What was the stupidest fight or argument that you ever had?


  1. How often do you check your phone?


21 questions to ask a guy over text infographic

  1. Do you play any video games? What’s your favorite?


  1. What do you think is the standard that makes someone “rich”?


  1. What are you good at cooking?


  1. What makes you feel alive?


  1. Do you like to take risks?


  1. Would you ever go deep sea diving or skydiving?


  1. What trips have you enjoyed the most?


  1. What was your largest purchase in the last year?


  1. Have you ever worked on a car? 


  1. What is your favorite chore?


  1. What skills do have that may surprise me?


  1. Use one word to describe yourself.


  1. How many close friends do you have?


  1. When do you like to dress in a suit?


  1. What are your favorite shoes to wear?


fun questions to ask a guy over text


Fun questions to ask a guy over text


  1. How often are you on your phone or computer?


  1. What was the last show that you watched?


  1. If you could step on a plane right now, where would you love to go?


  1. What do you procrastinate the most on?


  1. Who drives you crazy at your job?


  1. Would you be a better boss that the boss that you have now?


  1. What would you like to accomplish within the next year?


  1. What show can you watch for hours?


  1. What was the last time that you achieved a goal that you spent time planning for?


  1. What is your favorite thing to do on vacation?


  1. What would you like to change right now?


  1. Would you rather be indoors or outdoors on a hot summer’s day?


  1. How many days do you normally take off in a year?


  1. Would you ever like to start your own business?


  1. Would anyone describe you as a workaholic?


  1. What is your best memory of your brother or sister when you were kids?


  1. Do you have a creative outlet?


  1. What do you like to do for fun?


  1. What is your go to for take-out food?


  1. What was the best thing about your last relationship?


  1. Where do you spend the most time online?


  1. How good are you at poker?


  1. What was the biggest thing that you have ever won?


  1. What animal or bug freaks you out?


  1. What are your favorite breakfast foods?


  1. Can you rely on your friends if you really needed them?


  1. How often do you visit your family?


  1. Do you think kids are fun or annoying?


  1. What is your dream vehicle  or way to get around?


  1. What state or country would you live in if you could move?


  1. How many different jobs have you had?


  1. What comedy have you enjoyed recently?


  1. What do you spend money on?


120 random questions to ask over text



More questions to ask a guy over text


  1. What do you hate spending money on?


  1. When was the last time that you played a sport?


  1. What was the last party that you went to?


  1. Do you like surprises?


  1. Tell me a pick up line that you have either used.


  1. Are you a good gift giver?


  1. What are your favorite memories of your grandparents?


  1. How many times have you fallen in love?


  1. Do you take many photos?


  1. What Apps do you use the most?


  1. Have you ever bought something from a late night shopping commercial?


  1. What do you do impulsively?


  1. What was the last romantic thing that you have done?


  1. What would you enjoy doing if you were on vacation in Italy?


  1. Has anyone ever cheated on you?


  1. Would you ever forgive someone for cheating?


  1. What was a surprisingly really good movie?


  1. What would be really fun to experience in virtual reality?


  1. What career did you want when you were a kid? How close did you get?


  1. When was the last time that you were silly or did something goofy?


  1. Who was the last person that you had an argument with?


  1. What would you go back to school for?


  1. If you could start over, would you have the same career?


  1. How much money is enough?


  1. Are you good at trivia?


  1. What’s the worst part of your job?


  1. What was the most stressful thing that has happened to you?


  1. What are you passionate about?


  1. What are your thoughts on politics?


  1. Have you ever gone or wanted to go to a protest?


  1. What’s the best pet that you can have?


  1. Who do you admire?


  1. Are you a good driver?


  1. Tell me a good story about something that happened to you.


  1. Can you dance? 


  1. When was the last time you danced?



21 random questions to ask a guy over text infographic



 Questions to ask a guy 


  1. Do you think that you are easy to get along with?


  1. Who is the funniest person in your family?


  1. Do you have a sweet tooth?


  1. Would you rather do a food tour or a wine tour?


  1. Do you like amusement parks? What’s your favorite ride?


  1. Have you ever been to Disney World or land? 


  1. If you have gone to Disney, what was a favorite memory?


  1. Who is your best friend?


  1. What was the worst decision that you have ever made?


  1. Where do you take friends when they come to visit you?


  1. What makes you nervous?


  1. When was the last camping trip you went on? 


  1. Do you enjoy hiking or boating?


  1. Would you rather go biking or running?


  1. What is your idea of a fun date with someone new?


  1. When was the last time you went on a road trip?


  1. Do you enjoy planning adventures?


 121. If you found $100 in  your pocket, what would you spend it on?


130+ Ice breaker Questions & Texts to have Amazing Conversations

80 Conversation Starters for Texting that Spark Connections


questions to ask a guy over text infographic


What are good questions to ask a guy while texting?


Use our questions to have easy and insightful conversations. The best questions are the ones that allow you to get to know him a little bit better. 


Good conversations are like ping pong games, you ask the questions and then follow up on the answer. Asking any question is just a starting point. The real interesting answers come from the follow up stories.


30 Texts to Make Him Think About You & Intensify Attraction


What flirty questions to ask a guy you like?


The best flirty questions to ask a guy you like, will depend on how well you know him. We have great flirty conversation starters for any situation. 


113 Flirty Questions to Ask a Guy (to spice things up!)

75 Flirty Texts for Him to Make Him Want You


What should I talk about with a guy over text?


All you have to do is have a starting point. Use one of our questions and then after he answers, use something that he said in response for the next question. 

Most people like to talk about themselves so it’s usually easy, once you get started.


How to Start a Conversation Over Text (that Can’t be Ignored)


What are interesting questions to ask a guy?


Pick something to get to know more about his personality. When you know something about him, you can dive into the subject with more detail and interest.


101 Interesting Questions to Ask for Engaging Conversations


Conclusion Questions to ask a guy over text

Have fun with all of our questions! Visit our flirty questions to deep questions over text that help to increase intimacy. We have lots that will help you really get to know him or her. Cheers!

Share this article