101 Conversation Starters for Texting to Spark a Connection

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Imagine this for a second… 

You found someone that you’re interested in. 

You want to get to know this person, but you don't know what to talk about. 

Believe me: 

We've all been there. 

Fortunately, one quick strategy that can help is to try to a few conversation starters by text that can spark that connection.

In this article, we will give you 101 texting conversation starters that will keep someone engaged and wanting to reply to the messages that you send them!

But first, let’s start with a quick definition…

What is a Conversation Starter?

A conversation starter is an open-ended question that will not end up leaving you with a yes or no answer. These questions are meant to be thought-provoking and insightful on the individual that you are trying to get to know. 

For example, if you ask someone how their day was, you may get a simple response of “good” or “bad”. 

However, if you ask someone “what was the highlight of your day?” you may end up provoking a question that requires a longer answer and thus a conversation can begin to engage. 

People love to talk about their interests and these questions are a great way to get someone to open up to you with little effort. 

So let’s dive into the specific questions you can ask while texting.

101 Conversation Starters for Texting

1. What is something that everyone likes that you don't find popular?

2. What was a project that you worked really hard on?

3. What things were you really into as a kid?

4. What is a really annoying trait that someone can have that you don't like?

5. What is one thing that you cannot leave the house without?

6. Was there ever a time you were stuck on an awkward date with someone?

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A conversation starter is an open-ended question that will not end up leaving you with a yes or no answer.

7. What was the best vacation spot you have ever visited?

8. …what was the word vacation spot you have ever visited?

9. What is your guilty pleasure?

10. What trends pique your interest now that you think more people should follow?

11. What's an irrational fear that you have?

12. What is one thing that you're really good at?

13. What's your favorite TV show?

14. What cartoons were your favorite whenever you were growing up?

15. What is your favorite video game of all time?

16. What is something that you were completely obsessed with right now?

17. What places around the world have you never been to but want to visit?

18. What is your hidden talent that you haven't shared with anyone?

19. Have you ever meditated before?

20. What app do you use the most on your phone?

21. What is your opinion of social media?

22. What is your favorite kind of food?

23. How did you overcome a big challenge or fear in your life?

24. What are some deal breakers in a relationship that you don't want?

25. How much of your bucket list have you completed?

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26. What is something that is popular that you don't think should be popular at all?

27. What is your driving passion in life?

28. In a perfect world, what profession would you work in?

29. What is your favorite Netflix show?

30. What was the best day of your life?

31. What is your favorite time of day?

32. Do you drink coffee or tea?

33. What is something that you're not really good at?

34. What is your favorite scent?

35. Do you like any comedians and if so which ones?

36. Are you a spiritual person?

37. What is your astrology sign?

38. What did you study in college?

39. What are you going to do this weekend?

40. What is your favorite kind of music?

41. If you could do anything in the world right now what would it be?

42. What is your favorite season of the year?

43. What have you learned from the COVID-19 pandemic since we've all been indoors for most of the year?

44. Who is your best friend and what is their most admirable quality?

45. If you could pick up any hobby right now and master it what would it be?

46. Do you surf the internet often and if you do what do you like to read up on or watch?

47. Have you ever tried making a YouTube channel before?

48. What was your favorite moment from high school?

49. How would you describe yourself with only one word?

50. What is your favorite part about being in a relationship?

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51. What are some of the most important aspects of a relationship that you are looking for?

52. If you could go on a first date anywhere, where would it be?

53. Do you use dating apps and if so what was your worst experience with them?

54. How would you like to spend your free time in a relationship if you were in one?

55. What did you study whenever you were in school?

56. What do you like better: cats or dogs? Or both?

57. Are there any special quotes out there that have a lot of meaning to you?

58. Do you have a mentor or someone who has inspired you to become a better person?

59. What places in the U.S have you visited?

60. What is the worst pickup line you've ever had said to you before?

61. What does being successful mean to you as an individual?

62. If you have a bucket list, what is the most important item on your bucket list?

63. What was your first paying job, and how much did you make per hour?

64. Are you a realist, pessimist, or optimist?

65. If you could have any of these, which would you choose: personal driver, personal chef, personal trainer, or maid?

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Being a good question asker and a listener is a great way to win your future partner over.

66. What one thing would you change about your past if you had the chance to do so?

67. If you could visit a fortune-teller who really knew what they were doing, would you want to know about your past or your future?

68. What book are you reading right now, and are you reading it in hard-copy, audiobook, or on an e-reader?

69. Pretend you could fix just one of the world's biggest problems. Which major world problem would you like to fix?

70. If you could time-travel and choose your own name, what would you name yourself?

71. Speaking of time travel, if you could live during any other time in history, when would you choose to live and why?

72. In your most memorable childhood memory, who were you with at the time?

73. How old were you when you experienced your first love?

74. What one thing did you have to learn the hard way? 

75. If you could go back and live your childhood over again, would you want to grow up in the exact same place?

76. In the next lifetime, do you want to have the same parents? 

77. Thinking back to your high school best friend, what was your favorite trait about that person? 

78. What is your favorite childhood tradition that you hope to one day do with your own children? 

79. Do you believe that little white lies are totally OK as long as no one is hurt by them? 

80. When you have some good news to share, who is the first person you call? 

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81. Where are your ancestors from, and do you identify with the culture that they came from? 

82. On the worst day imaginable, do you prefer to be left alone or do you recharge by being around other people and having a good time? 

83. If your house was on fire and you could grab just three things (not counting people and pets), which three things would you grab? 

84. If you ever decided to start a small business, what do you think you would be most successful at? 

85. If you found yourself stranded on a deserted island, would you prefer to be with your worst enemy or alone with no one but yourself? 

86. Looking back over your lifetime, which decade did you most enjoy and why? 

87. If aliens landed on the planet today and wanted someone to go with them back to their planet, would you volunteer to go? 

88. Which celebrity actor would you want to play you in the movie about your life? 

89. Think about all of the fictional characters you've ever known. Which one of them would you like to have as your best friend? 

90. When you were a child, what did you want to be when you grew up? 

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People love to talk about their interests and these questions are a great way to get someone to open up to you with little effort. 

91. Pretend that you have been given (or you have hired) a personal assistant. What tasks would you have them do for you? 

92. If you could suddenly be an expert at one thing, what would that one thing be? 

93. Which language do you wish you spoke fluently? 

94. If any human being in history could be your best friend, who would you choose and why? 

95. Would you rather time travel to meet your ancestors or travel to the future to meet your progeny? 

96. If you suddenly had a million dollars to give away and you had to give it to a charity, which charity would you choose? 

97. What is one thing you wish teenagers today could learn from older generations? 

98. If you could watch one movie again for the very first time, which movie would you choose? 

99. As a child, what was your least favorite food? Do you still dislike that food today? 

100. Has anyone ever told you that you resemble someone famous? Who is your celebrity doppelganger? 

101. How many cups of coffee or tea do you have every morning, and can you function without it? 

Final Thoughts on Texting Conversation Starters

People have more options when it comes to dating nowadays than ever before. Simply being a nice person with no personality will not work when it comes to standing out. 

Fortunately, these questions are a great way to learn the aspects of the art of conversation. Being a good question asker and a listener is a great way to win your future partner over. And if you want to see more great conversation starters, then be sure to check out our post on fun hypothetical questions you can ask someone and our article on open ended questions examples to help start a lively conversation.

Finally, if you want to ask better questions, then watch this short, 20-minute course to learn how to have a great conversation with virtually anyone.

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101 Conversation Starters for Texting to Spark a Connection