100 Conversation Starters Over Text to Keep the Conversation Going

Last Updated on November 3, 2022 by Michele Tripple

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We are all on our phones a million times a day either talking, texting, playing truth or dare over text, or another fun game with friends and family. But what happens when you want to start a conversation over text with someone new. What do you say? How do you keep it going? This list of conversation starters over text will help you start a conversation and keep the conversation all night long!

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How to Start a conversation over text

We have all been there. We want to start a conversation over text, but have no idea how. Here are some tips to start a conversation over text with someone.

  • Send a compliment that is genuine and authentic
  • Send a funny picture, quote, or GIF
  • Ask them about something that happened that they would know about.
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100 of The Best Conversation Starters Over Text

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  • What was the best year of your life so far?
  • Serious question: Do you think I could pull off leather pants?
  • What’s your “go-to” video or gif for a laugh?
  • What is something you are totally obsessed with right now?
  • What’s your favorite thing to do on the internet?
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  • What do you think is the most annoying thing a person can post on their Insta Story?
  • Where’s your favorite place to get take away or delivery from?
  • I am thinking about getting a pet. Do you have one? Which kind?
  • What do you spend most of your time doing?
  • If you could be trapped in an elevator with any celebrity for 12 hours, who would it be and why?
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  • What song do you play most often?
  • What’s your opinion on flip flops? Unsightly or essential?
  • What do you spend way too much money on?
  • What’s the closest thing to real magic?
  • What’s your favorite quote from a movie?
  • Who is the messiest person you know?
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  • Who do you have a hard time taking seriously?
  • What will finally break the internet?
  • What’s your “go-to” joke?
  • What’s the most useless talent you have?
  • What do you judge people for most often?
  • What would be on the gag reel of your life?
  • What song has the best intro?
  • Where is the worst smelling place you’ve been?
  • What’s your favorite thing to shop for? Why?
  • What celebrity would you rate as a perfect 10?
  • Where was the last place you went on vacation?
  • What’s a body part that you wouldn’t mind losing?
  • What’s the best compliment that someone can receive?
  • What is the dumbest way you’ve been injured?
  • What’s the funniest text you’ve gotten?
  • Which fictional character would be the most boring to meet in real life?
  • What’s the most disappointing text you’ve gotten?
  • If you had to change your name, what would your new name be, and why would you choose that name?
  • What’s the weirdest text you’ve gotten?
  • What are some things that sound like compliments but are actually insults?
  • What’s something you can do that most people can’t?
  • What’s your biggest screw up in the kitchen?
  • What is your favorite meme?
  • What’s the worst commercial you’ve recently seen? Why is it so bad?
  • How do you calm yourself down when you are angry?
  • What is the craziest thing one of your teachers has done?
  • What is the most interesting thing you have on you or near you right now? Send me a pic of it.
  • What’s the funniest thing you ever did?
  • Who’s your oldest friend?
  • What’s something your brain tries to make you do and you have to will yourself not to do it?
  • What app on your phone do you think I should get?
  • If you could know the absolute and total truth to one question, what question would you ask?
  • What do you find hilarious but most people don’t find funny?
  • What’s the most interesting thing you’ve read or seen this week?
  • What’s the best photo you’ve taken?
  • What ridiculous thing has someone tricked you into doing or believing?
  • What was the most beautiful view you have ever experienced?
  • What was your best drop the mic moment?
  • What’s the worst text that you accidentally sent?
  • What childish thing do you still enjoy?
  • What fad have you held on to, even though it isn’t popular anymore?
  • What’s the biggest doubt you have?
  • What thing do you really wish you could buy right now?
  • Where is the best place you have ever been?
  • What event small or large has changed the course of your life the most?
  • How many phones have you broken or lost?
  • What’s the funniest thing that someone could spend money on / buy on the internet?
  • Who or what is your nemesis?
  • What is something you have read or heard that has stuck with you for a long time?
  • What is the most useless thing you know how to do?
  • What’s the funniest picture you have on your phone?
  • What’s the worst and best thing about being male/female?
  • What’s something that people go on and on about, and you just can’t take sitting through?
  • What is something that most people get wrong?
  • What dumb pickup lines do you know?
  • What would you NOT do for 5 million dollars?
  • When was the last time you tried to do something to look cool and it ended in utter embarrassment?
  • What’s your best flirty text?
  • What are some unwritten rules?
  • You wake up suddenly in the middle of the night. What would be the scariest sound to hear after waking up?
  • What is the most cringe-worthy thing you have seen someone post on social media?
  • What would be the consequences of a scientific discovery that extended the life span of humans to 500 years?
  • What happens in real life but rarely gets portrayed in movies?
  • What movie can you watch over and over and never get tired of?
  • What is the most ridiculous rule you have to follow?
  • If you designed and built a treehouse, what would it look like and what would be in it?
  • What isn’t real but you desperately wish it was?
  • What is the most interesting piece of trivia you know?
  • What bullet have you recently dodged?
  • Which celebrity would make the worst leader of a country?
  • What’s the best “hidden gem” that you’ve found?
  • What brings you the most joy?
  • What country do you not know the location of even though you should?
  • What’s something you were really stressed about, it turned out to be no big deal?
  • What’s the silliest thing you are passionate about?
  • What are you tired of hearing about?
  • What do you have a hard time with but most people find quite easy?
  • What do you bring with you everywhere you go?
  • What do you hate most about your phone?
  • What do you love most about your phone?
  • What’s the most impressive skill you have?
  • What’s the most ridiculous thing you’ve seen online recently?
  • What’s a huge story in the news that you care absolutely nothing about?
  • What would you name your boat if you had one?

There you have it! The best conversations over text! What questions would you add to the list? Share in the comments!

Looking for more fun with friends? Try these posts!

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1 thought on “100 Conversation Starters Over Text to Keep the Conversation Going”

  1. These are all such great suggestions! They would be so applicable to people who are early in their relationship too! So many of these questions require some thought and a great chance to get to know others on a deeper level. So awesome!


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