Fun Dating Sites

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.

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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?

Dating

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?

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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?

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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?

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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?

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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?

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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?

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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!

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'What's your favorite snack besides me?'

Originally Published:

Whether or not you ever pictured yourself picking up potential partners on a dating app, it's kind of an inevitable part of the world we live in now. And, depending on who you ask, dating apps are either a stellar resource or a major source of stress. Between figuring out the right questions to ask on a dating app, navigating the unspoken rules about the frequency of messages, and crafting a profile that captures your personality, there’s a lot of thought that goes into a successful dating profile. If you find yourself overwhelmed by the prospect of coming up with dating app questions that will help break the ice, you’re not alone.

“It’s not uncommon for my clients to need help at the beginning of an online flirtation,” says Toronto-based dating expert and breakup coach Natalia Juarez. “We’ll look at a couple profiles that they really like in a session and brainstorm together all the things they could say to this person. Oftentimes my clients just need to talk things through, but then eventually they start self-coaching and it comes a lot more naturally. Once they just see how many possibilities there are for starting a conversation, they feel much better.”

When kicking off a conversation on a dating app, it can also be helpful to have a sense of what you don’t want to do. “Don't be boring,” Juarez cautions. “The ‘Hey, how are you’ and ‘How was your weekend’ opening lines? I can’t believe people are still doing that! It’s so lazy, and you’re making me do all the work!” Instead, Juarez says simply showing a bit of imagination will go a long way.

In the end, Juarez acknowledges that for many women, the idea of taking the reins of the conversation can be intimidating, especially because women have been socialized to cede control to men. If you struggle with this, Juarez has a solution. Instead of thinking of your opening line as an active pursuit of your match, she says to think of it more as a lure. “It’s a green light, an invitation. With your opening line, you’re saying ‘the door’s open.’ It’s like being at a restaurant, looking over, and smiling at someone. It’s just inviting.”

So go ahead and flash that green light, hit the gas, and cruise on into the flirtationship of your dreams with these clever questions to ask on a dating app.

Remember that episode of Friends when Ross and Rachel make their lists of celebrities that they're allowed to cheat on each other with? Everyone’s got their list, whether they admit it or not. And who cares if the chances of meeting Tessa Thompson and hooking up with her are pretty slim? This flirty question is bound to get the conversation flowing.

You’ll instantly be able to see if you’ve snagged yourself a Nobel Prize–winner who thanks their mom, or a Kids’ Choice Award–winner who says their hero is “me in 10 years” à la 2014 Matthew McConaughey.

When in doubt, get creative and don’t overthink it — it only takes one great question to open up a world of possibilities.

Experts:

Natalia Juarez, breakup and dating coach