With phones being inundated by robocalls and that persistent guy trying to sell a piece of a timeshare, talking on the phone has become more of a chore rather than a special moment. That smartphone rings and we immediately look at it and dread the unrecognized number on the caller ID. If you are really close with someone and want to strike up a conversation, what do you do? You text. It’s also the easiest way to reach out to a potential match without another person hearing a tremor in your voice. You can just leave it out there and once sent, you are done (well, unless you want to dwell over it and unsend, send and then unsend again). Texting is usually the preferred option when working on a match, but that does not mean it is easy. These 100 conversation starters for texting are here for when texting starts to feel as taxing as that robocall. 

Let these conversation starters for texting be a how-to on keeping a dying text conversation alive. In other words, avoid dry texting that has you gasping for water by the time you hit “send.” So, what are you waiting for? Warm up those thumbs with these 100 conversation starters and keep-the-party-going texts.

Conversation Starter For Texting Someone You Want To Catch Up With

  • Hey! It’s been way too long. What have you been up to lately?
  • Remember that crazy adventure we had? Tell me, what’s your favorite memory from it?
  • I heard you started a new job. How’s it going? Tell me all about it!
  • If you could travel anywhere right now, where would you go and why?
  • What’s a new hobby or interest you’ve picked up recently?
  • Netflix has been dropping some great shows lately. Any recommendations?
  • How have you been staying active or fit these days?
  • I’ve been trying to cook more. Got any favorite recipes to share?
  • Do you have any upcoming plans or trips you’re excited about?
  • What’s something that’s made you laugh out loud recently?
  • Have you discovered any amazing books or podcasts lately?

Conversation Starters For Texting Someone You Want To Catch Up With

  • Let’s reminisce! What’s a childhood memory that always brings a smile to your face?
  • If you could meet any historical figure, who would it be and why?
  • What’s a goal or aspiration you’re working towards right now?
  • Tell me about a recent accomplishment or something you’re proud of.
  • Do you have a favorite quote or mantra that’s been motivating you lately?
  • What’s the most delicious meal you’ve had recently, and where was it?
  • I’ve been on a music discovery kick. Any new favorite songs you can recommend?
  • If you could change one thing about the world, what would it be?
  • Let’s play a fun hypothetical game: If you had a time machine, where and when would you go first?

Funny Conversation Starters For Texting

  • If you were a vegetable, which one would you be and why? I think I’d be a potato because I’m always up for some couch-potato time!
  • Do you believe in aliens, or do you think we’re just the universe’s biggest reality TV show?
  • If you could have any superpower but only use it for everyday annoyances, what would it be?
  • What’s your go-to dance move when no one’s watching, and can you describe it in emojis?
  • If you could only eat one food for the rest of your life, what would it be? (Nope, “pizza” is not an option!)
  • Have you ever had an embarrassing moment that still makes you cringe when you think about it?
  • Quick! You’re stranded on a deserted island, and you can only bring three things with you. What are they?
  • If your life were a movie, what would its tagline be?
  • Would you rather fight one horse-sized duck or a hundred duck-sized horses? (And why?)

Fun, Lighthearted Make Great Conversation Starters For Texting

  • If you could swap lives with any fictional character for a day, who would it be and why?
  • Tell me the weirdest food combination you’ve ever tried and secretly loved.
  • If you could have a conversation with any inanimate object, which one would it be and what would you talk about?
  • Describe your last grocery shopping trip using only emojis.
  • If you could make up a new holiday, what would it be called and how would we celebrate it?
  • What’s the most unusual or hilarious pet name you’ve ever heard?
  • If you could be a professional at any silly or obscure talent, what would it be?
  • Do you have a favorite dad joke or pun that always makes you laugh?
  • Let’s settle the debate: Is cereal a soup? Why or why not?
  • If you were a character in a video game, what would your special power-up be?
  • If you had to survive a zombie apocalypse with only the items in the room you’re in right now, how long do you think you’d last?

Everyday Questions To Keep The Conversation Flowing

  • Hey, how’s your day going so far?
  • “Did you catch the latest episode of [popular TV show]? What are your thoughts?”
  • Did you have a good weekend? Anything exciting happen?
  • Have you tried any new restaurants or cafes recently? Any recommendations?
  • What’s the last movie or TV show you watched, and did you enjoy it?
  • Are you working on any interesting projects or tasks lately?
  • Do you have any fun plans for the upcoming weekend?
  • I just tried a new recipe, and it turned out pretty good. Do you enjoy cooking?
  • How’s your family doing? Anything new with them?
  • Have you read any good books lately? I’m looking for some recommendations.

Ways To Start A Conversation With Someone That Just Got Off Work

  • What’s your favorite way to relax and unwind after a long day?
  • Have you been following any interesting news or current events recently?
  • Do you have any upcoming vacations or trips you’re looking forward to?
  • I’m in the mood for some new music. Any song or artist suggestions?
  • Have you been keeping up with any hobbies or activities lately?
  • Are you into any sports or sports teams? How are they doing this season?
  • Tell me about your favorite local spots to hang out or grab a bite to eat.
  • Do you have any plans for the upcoming holidays or special occasions?
  • How’s your work or school going these days? Any challenges or successes to share?
  • What’s something that made you smile or laugh today?

Flirty Conversation Starters For Texting Your Crush

  • “I couldn’t help but smile when your name popped up on my phone. 😊 What’s making you smile today?”
  • “If you could choose any place in the world for a spontaneous getaway, where would it be?”
  • “What’s your favorite type of date night: a cozy night in or an exciting night out?”
  • “I have this feeling that we’d make an incredible team in a game of [choose a game]. What do you think?”
  • “I just saw something that reminded me of you, and it made my day. Care to guess what it was?”
  • “What’s your idea of the perfect date night? I’m curious.”
  • “If you could have any superpower, what would it be, and how would you use it to impress someone?”
  • “I’ve been daydreaming about our next adventure together. Any ideas?”
  • “I’m terrible at keeping secrets, especially when it comes to how much I enjoy texting you.”
  • “If we were characters in a romantic movie, what would our meet-cute be like?”

Thought-Provoking Conversation Starters For Texting

  • “What do you think is the most pressing issue facing society today, and how can we address it?”
  • “If you could have a conversation with any historical figure, who would it be, and what would you ask them?”
  • “What’s one life lesson you wish you had learned earlier, and how has it influenced your life since?”
  • “Do you believe in fate, or do you think we have the power to shape our own destinies?”
  • “If you had to choose between pursuing your passion and achieving financial stability, which would you prioritize and why?”
  • “What’s the most meaningful book you’ve ever read, and how did it impact your perspective on life?”
  • “If you could travel back in time to any era, where and when would you go, and what would you want to witness or experience?”
  • “What’s the one thing you want to accomplish in your lifetime that you haven’t tackled yet?”
  • “If you could have a dinner party with any three people, living or dead, who would they be, and what’s the topic of conversation?”
  • “How do you define success, and do you think you’re on the path to achieving it?”

Questions That Allow An Open And Honest Conversation

  • “What’s a belief or opinion you’ve held for a long time but have recently started to question?”
  • “If you could change one thing about the education system, what would it be, and why?”
  • “What’s the most significant challenge you’ve faced in your life, and how did it shape you?”
  • “Do you think technology is bringing us closer together or driving us further apart as a society?”
  • “If you could choose one historical event to witness in person, which would it be, and why?”
  • “What’s your take on the concept of happiness? Is it a destination or a journey?”
  • “How do you think the world will be different in 20 years, and what role will you play in that change?”
  • “If you could give your younger self one piece of advice, what would it be?”
  • “What’s a topic or issue you’re passionate about, and how do you express that passion in your daily life?”
  • “What’s the most valuable lesson you’ve learned from a failure or mistake?”
  • “With so many reboots and sequels, is there a classic movie or TV show you’d love to see revived?”
  • “Who’s your all-time favorite actor or actress, and why do they resonate with you?”
  • “What’s the last song you couldn’t stop listening to?”
  • “Do you listen to any podcasts? Any interesting episodes you’d recommend?”
  • “Which fictional character from a book, movie, or TV show do you think you relate to the most?”
  • “If you could have a cameo in any TV series or film, which one would it be, and what kind of character would you play?”
  • “The entertainment world is always full of surprises. Any recent pop culture news that caught your attention?”
  • “What’s the most memorable concert or live performance you’ve ever attended?”
  • “If you could attend any major pop culture event (Comic-Con, award show, etc.), which one would it be, and why?”
  • “Let’s settle a debate: Star Wars or Star Trek? Which one’s your favorite, and why?”
conversation , dating , relationships , texting