How do you feel about classes starting again?
What was the most fun you had during the break?
Tell me about your New Years!
What's the latest you slept in during the break?
What is something that you made during the break?
What was the most boring day during the break?
....
Did you travel anywhere during the break?
What is something that made you laugh over the break?
What was the best movie/show you saw during the break?
Tell me about any holidays you celebrated!
What is something you ate during the break that you found delicious and something that you found disgusting?
What's the latest you stayed up during the break?
What chores did you do at home during the break?
When you had free time, what did you do over break?
What are you looking forward to this year?
What was the weather like over your break?