70 Conversation Starters for Dating Online or Off

A couple at a table using one of these conversation starters for dating to chat about while they sip coffee.

Initiating conversation with a total stranger, or someone you barely know, can be tough—especially if you’re not used to encounters like this, or you consider yourself to be fairly quiet or introverted.

Whether you’re chatting with someone you’re interested in on a dating app or in real life, it’s so helpful to have some interesting conversation starters on hand ready to throw out there.

Not only does this help avoid awkward silences, but it also helps you get to know each other, and see whether you’re compatible or not—which is essential when it comes to dating.

Great conversation starters can lead to deeper, and more meaningful conversations, which means better dates, and stronger connections.

Here are 70 fun, and interesting conversation starters to get you off to a flying start:

1. What are your favorite things to do on weekends?

2. Who are three of the most important people in your life?

3. What is a skill you wish you had?

4. Do you find it easy to open up to people?

5. What are you passionate about in life?

6. What kind of friends did you have in secondary school/high school?

7. Are you an introvert or an extrovert?

8. Are you good at keeping secrets?

9. What’s the most thoughtful thing someone has ever done for you?

10. What is your favorite type of food, and why?

11. What are three words that you’d use to best describe yourself?

12. What do you look for in a friendship?

13. If you could pursue any career, what would you choose to do?

14. What are you watching on Netflix right now?

15. Do you have any regrets in life?

16. How romantic are you on a scale of 1-10, with 1 being not romantic at all?

17. What’s the most spontaneous thing you’ve ever done?

18. What is your favorite drink?

19. Where’s your favorite place that you’ve lived?

20. What is the best advice you’ve been given?

21. If you had three wishes in life, what would they be?

22. If Morpheus offered you the blue pill and the red pill, which one would you take?

23. Where is your favorite place in the world, and why?

24. What life accomplishment are you most proud of?

25. If you had a superpower, what would it be?

26. When something bad happens, who do you talk to first?

27. If you could any 3 people — past or present — to a dinner party, who would you invite?

28. If you had a theme song, what would it be?

29. What would your perfect first date look like?

30. What is your spirit animal?

31. Do you prefer texting or speaking on the phone?

32. If someone cheated on you, what would you do?

33. What was your favorite class at school?

34. What was the best part of your day today?

35. What’s your favorite book, and why?

36. What is the worst thing someone could do on a date with you?

37. What would your signature dish be on Masterchef?

38. What is the worst pickup line you’ve heard?

39. If you could only eat 5 things for the rest of your life, what would they be?

40. If you were on death row, what would you choose as your last meal on earth?

41. What’s the first thing you do when you wake up in the morning?

42. Have you ever had a really awkward date?

43. What is your Myers Briggs type?

44. Do you believe in a higher power?

45. If you could stop time, what would you do?

46. Do you believe in marriage?

47. If you were given a lump sum of money to start a business, what kind of business would you start?

48. What is your favorite animal?

49. You’re going to live on a desert island for 3 months — what 3 things would you bring with you?

50. If you could buy a plane ticket to anywhere, where would you choose?

51. What is your favorite way to stay healthy?

52. What is more important — doing what you love, or doing what you’re good at?

53. If you would time travel, where would you go?

54. If you won the lottery, what would you do with the money?

55. If you knew today was your last day on earth, what would you do?

56. What’s your favorite movie of all time, and why?

57. Tell me your biggest fear?

58. What did you want to be when you were a child?

59.. What is your family like?

60. Where do you want to travel to next?

61. What qualities do you look for in people you date?

62. Are you close to your family?

63. What has been the best year of your life so far?

64. What is the scariest thing that’s ever happened to you?

65. What is a saying that you try to live by in life?

66. What is your favorite dessert?

67. Do you have any celebrity crushes?

68. Do you think aliens exist?

69. Do you believe in astrology?

70. Have you changed much over the past ten years?

Try some of these out next time you’re talking to someone you don’t know, and see where they take you!

Shani Jay

Bestselling Author and Empowerment Coach

Shani is a bestselling author, empowerment coach for women, and self-love advocate. She is the author of Bloom, The Babe Bible, Glow Getter, and Light Up Your Life; and her writing has been featured on many internationally recognized platforms including The Huffington Post, Thought Catalog, and Teen Vogue.

​In 2016 Shani founded The Glow Getter Tribe – a self-love & kindness movement which helps young girls & women worldwide feel happy, confident and beautiful starting from the inside, out.

No Comments Yet

Comments are closed

Weekly Dating Insider