As children enter adolescence and spend more time away with friends or on their own, it easy for parents to feel a bit disconnected. When we do get a chance to interact, this gap can make conversations awkward and difficult to start, leading to old standby questions like “How was school?” that rarely get meaningful conversations started. 

With some help from my oldest son, Jackson Rettew, and his classmates at the Mount Mansfield Union High School in Jericho, Vermont, here are a list of 100 alternate questions that parents might consider asking their teenage kids. We tried to avoid those that might come up on college essays or job interviews. Some are serious, others are light-hearted. And, of course, many may not be appropriate or apply to your own family. Nonetheless, here they are for your consideration, presented in no particular order. We hope at least some might be useful to try.

1. What are the different cliques or social groups in your school and which one, if any, are you in?
2. Do you have a celebrity crush?
3. What is the coolest app that I don’t have on my phone?
4. What is the most embarrassing thing that I do?
5. Who do you eat lunch with at school?
6. How would you describe my parenting style?
7. What bands are you listening to these days?
8. Can you play me one of their best songs?
9. Who would you say is your best friend right now?
10. Where would be an awesome place to go for a family vacation?
11. What do you think of President Trump?
12. What do you think of my hair style?
13. Did I ever tell you about how I met your (mother, father)?
14. Who is your favorite and least favorite teacher this year?
15. Which shows are you watching right now? 
16. Any of those shows you’d recommend for me?
17. Do you think aliens exist?
18. How male or female do you feel inside as you get older?
19. Is there anything you would like to learn how to do?
20. Have there been any books that you had to read this year that you really liked?
21. How would you describe your personality?
22. How would you describe my personality (or the other parent)?
23. Is bullying a problem at your school?
24. Is drug and alcohol use a big thing at your school?
25. What is the one thing you don’t know about me that you want to know?
26. What are some of the first things that you remember?
27. Which holidays do you really like and why?
28. Which holiday do you wish never existed?
29. What look are your going for when you get dressed?
30. How long do you want to live?
31. What would you say were the most important moments of your life so far?
32. What would you wish I might do differently as a parent?
33. If you could someday drive any car or truck you want, what would it be?
34. Do you believe in God?
35. What would you say are your all-time favorite movies so far?
36. What do you wish you were more motivated to do?
37. When you get older, will you vote as a republican, democrat, or independent?
38. Are there any quotes from movies, songs, or books that you’ve heard and really like?
39. Are there parts of your body that you really like or dislike?
40. Do you think our family has enough money?
41. What were the most memorable family trips we’ve taken so far?
42. Which specific memories stand out from them?
43. What do you do and think when you see a homeless person?
44. Do you know anyone who you would say has an ideal marriage or relationship?
45. How do you think the world will eventually end?
46. What was the funniest thing that happened today?
47. What is the best and worst food that your school cafeteria serves?
48. Do you ever feel jealous about the family of any of your friends?
49. Which teacher at our school is the scariest?
50. Do you think we treat you and your siblings fairly?
51. Can you teach me how to text faster?
52. Are there any celebrities that people say you look like?
53. Which songs have been stuck in your head?
54. What bumper stickers have you seen that you really like?
55. Do you think millennials are really that different from other generations?
56. What are the best and worst things about having a smartphone?
57. What do you like to watch on YouTube?
58. Do you like your voice?
59. Do you think you want to get married one day?
60. How many kids, if any, do you think you might want some day?
61. What kind of a parent do you think you will be?
62. If we could move to a different neighborhood or part of town, would you want to go?
63. How gross are your school bathrooms?
64. What thing about our house/apartment irritates you the most?
65. Are you looking forward to being an adult?
66. If you were allowed to get a tattoo, what would you get?
67. Do you think adults praise kids too much or not enough?
68. Do all these school shootings in the news make you feel unsafe at school?
69. What’s the one thing adults don’t get about teenagers?
70. What is your favorite snack food?
71. What should be the name of your generation?
72. What do you think is the best number of children to have?
73. If you wanted to have kids, what would you want to name them?
74. Are you more of a dog or cat person?
75. How’s your love life?
76. Do you have any enemies?
77. What would you do with a million (or billion) dollars?
78. Do you think teens have it easier or tougher compared to my generation?
79. What was the best part of your day today?
80. What was the worst part of your day today?
81. Where’s the first place you would want to go after getting your driver’s license?
82. Do you agree with the current legal age for drinking, smoking, and voting?
83. Did I ever tell you about my prom experiences?
84. Are you currently trying to lose or gain weight right now?
85. If two people like each other romantically, do you think someone still should ask before trying to kiss them?
86. How tall would you like to be, if you could choose?
87. Do kids your age still care about professional sports?
88. What do you think has been the hardest thing you have ever done?
89. What do you think the fourth dimension is?
90. What is the best (non-profanity) comeback to say to a bully?
91. Is it more awkward to address adults as Mr./Ms. or to use their first names?
92. If we had more money, how would you use it?
93. Do you wish we has pushed you harder or less hard to keep doing __________?
94. Are you satisfied with the number of friends that you have and quality of those friendships?
95. Do you think marijuana should be legal for people after a certain age?
96. If you had to be a mythical creature, what would you be?
97. What could I do to help you feel more supported?
98. What are the big things being talked about at school?
99. What were some of best holiday or birthday presents you ever received?

David Rettew, M.D., is a child psychiatrist and Associate Professor of Psychiatry and Pediatrics at the University of Vermont College of Medicine.