Because “So… how’s work?” is not the only option.

Family gatherings can be beautiful… and they can also be weird.

You’ve got:

• people on their phones

• someone bringing up politics (why are they like this?)

• teenagers giving one-word answers

• that awkward silence after the food is served

And everyone defaults to the same tired script:

“So… what have you been up to?”
“How’s work?”
“Still busy?”

Let’s upgrade the conversation.

Because you don’t need your family to be perfect — you just need a few better prompts.

This post gives you 101 conversation starters for family gatherings that create warmth, laughter, and real connection… without forcing deep therapy chats at the table.

How to use these without being awkward

Pick one of these options:

Option A: The Question Jar

Write questions on paper strips, put in a jar, pull one at a time.

Option B: One question per course

One question at the start, one at dessert.

Option C: Place cards with prompts

Pop one question at each seat.

Option D: “Winner gets dessert first”

Turn it into a light game. Keep it playful.

And yes — you’re allowed to say:

“Alright, phones down for two minutes. I’ve got a question.” 😊

101 conversation starters (grouped for easy picking)

A) Easy warm-up questions (1–20)

1. What was the best part of your week?

2. What’s something small that made you smile lately?

3. What’s one thing you’re looking forward to?

4. What’s your current favourite snack?

5. What’s a TV show or book you’re enjoying?

6. What’s a song you’ve had on repeat?

7. What’s your go-to comfort food?

8. What’s a little “win” you had recently?

9. What’s something you’re learning right now?

10. What’s one thing you’d love more time for?

11. What’s a place you’d love to visit?

12. What’s your favourite smell?

13. If you could have a free hour tomorrow, what would you do?

14. What’s the best thing you’ve eaten lately?

15. What’s your favourite season and why?

16. What’s something you’ve been proud of this month?

17. What’s one thing that’s been surprisingly hard lately?

18. What’s one thing that’s been surprisingly good lately?

19. What’s a hobby you’d love to try?

20. What’s a simple thing that helps you feel calm?

B) Family memories + laughs (21–40)

21. What’s a family moment you still laugh about?

22. What’s a funny thing you did as a kid?

23. What’s a family story you never get sick of?

24. What’s your favourite memory in this house?

25. What meal reminds you of childhood?

26. Who was your childhood hero?

27. What’s the most ridiculous family argument we’ve ever had? (Keep it light!)

28. What’s a family saying we all know?

29. What’s one thing you got away with as a kid?

30. What’s a family tradition you secretly love?

31. What’s one “classic” family photo we should recreate?

32. What did you want to be when you were 10?

33. What was your favourite birthday?

34. What’s a family holiday memory you still remember clearly?

35. Who in the family makes you laugh the most?

36. What’s the best prank you’ve seen (or pulled)?

37. What was your first job?

38. What’s the most chaotic family moment that turned out okay?

39. What’s something you learned from a grandparent?

40. What’s a meal we should keep making forever?

C) Getting to know adult kids + partners (41–60)

41. What’s something you wish people understood about you?

42. What’s your love language (or what makes you feel cared for)?

43. What’s something you’ve changed your mind about in the last few years?

44. What’s a value you’re holding tightly right now?

45. What’s a boundary you’re glad you set?

46. What’s a habit you’re trying to build?

47. What’s something you’re working on behind the scenes?

48. What’s a decision you’re proud of?

49. What’s something you want more of this year?

50. What’s something you want less of this year?

51. What does a “good day” look like for you?

52. What’s a moment recently where you felt grateful?

53. What’s a fear you’ve faced (even a small one)?

54. What helps you feel supported?

55. What do you wish you had more confidence in?

56. What’s a skill you’d like to learn?

57. What’s something you’re excited to teach someone?

58. Who has helped you the most lately?

59. What’s something you wish we did more as a family?

60. What’s one tradition you’d like to keep (or start)?

D) Grandkids + generations (61–75)

61. What’s something you want the younger generation to know?

62. What do you hope the kids remember about family?

63. What was your favourite game as a child?

64. What’s a song from your teen years you still love?

65. What’s one “life lesson” you learned the hard way?

66. What’s something you appreciate more with age?

67. What’s one thing you’d tell your younger self?

68. What’s a family skill we should pass down (cooking, gardening, fixing things)?

69. What’s a tradition you’d love the kids to experience?

70. What’s a memory you want to create this year?

71. What’s something you admire about the younger generation?

72. What’s something you want to learn from them?

73. What’s a family story the kids should hear?

74. What do you hope family feels like for them?

75. What does “home” mean to you?

E) Light-hearted “would you rather” (76–90)

76. Would you rather live by the beach or in the mountains?

77. Would you rather cook or be cooked for?

78. Would you rather have a fancy dinner or a picnic?

79. Would you rather go camping or stay in a resort?

80. Would you rather have one big holiday a year or small trips often?

81. Would you rather watch a comedy or a thriller?

82. Would you rather be early or fashionably late?

83. Would you rather spend a day reading or doing something active?

84. Would you rather have pets or no pets?

85. Would you rather never do dishes again or never do laundry again?

86. Would you rather host or bring a plate?

87. Would you rather have a family talent show or family games night?

88. Would you rather have a phone-free day or a social-media-free week?

89. Would you rather eat dessert first or last?

90. Would you rather relive your teens or skip them entirely?

F) Gentle, meaningful questions (optional depth) (91–101)

91. What are you thankful for right now?

92. What’s something you’re hoping for?

93. What’s something you’re letting go of?

94. What do you want your life to stand for?

95. What’s a moment you felt truly loved?

96. What do you want our family to be known for?

97. What’s one thing you want to be remembered for?

98. What’s a belief or principle that guides you?

99. What’s something you need more of (rest, fun, help, time)?

100. Who has shaped you in a good way?

101. What’s one way we can support each other better?

A midlife note (because you’re probably the one leading this)

If you’re reading this, there’s a good chance you’re the one who:

• wants the gathering to feel warm

• notices when people disconnect

• tries to keep the peace

I see you.

But here’s your reminder: you don’t have to carry the whole emotional weight.
Sometimes all it takes is one good question — asked with kindness — to shift the room.

Wrap-up (save this for your next gathering)

Pick 10 questions. Save them in your Notes app. Use them on repeat.

Because connection doesn’t need perfection. It needs attention.

Until we chat again,

Blessing & hugs to you my dear friend,

Dianne xx