This is my go-to question and it comes up very naturally if someone talks about 1. being busy 2. what they do for a living 3. any hobbies It can transition you into a nice, broad discussion about hobbies and how they spend their time. It’s so much better than “What are your hobbies?”
Are you working on any personal passion projects?
If it is around the holidays or one of your birthdays, you can talk about presents. This is also a great one if there is a birthday in the restaurant you are eating in!
What’s the best present you ever gave someone? Ever received?
Don’t ask, “What do you do?” Instead, ask them about their typical day. This question will give you much more robust answers and you will learn far more about a person than just asking,
What does a typical day look like for you?
This one comes up quite easily if you are ordering food. It can produce some really easy conversation and might provide you with some great tidbits.
Is there anything you don’t eat?
People often ask, “Have you gone on any vacations recently?” However, someone can answer that very quickly—and they might not have gone anywhere (which results in awkward silence). Instead, try asking what kinds of vacations they like to take.
What sort of vacations do you like to take?