Japanese conversation questions with natural follow-ups
Bring two questions you actually want answered. A follow-up about one word in the answer usually gives you more to talk about than a third unrelated question.
Make an agenda for your interestsFree time and routines
週末は何をすることが多いですか？ (What do you usually do on weekends?) If they mention an activity, try それはいつから始めたんですか？ (When did you start doing that?) Then tell them how you spend a similar afternoon.
平日の朝は何をすることが多いですか？ (What do you usually do on weekday mornings?) Follow with 朝ごはんは何を食べますか？ (What do you eat for breakfast?) if food came up.
Places and a way back into the conversation
よく行く場所はありますか？ (Is there somewhere you go often?) If they name a place, ask そこでは何をするのが好きですか？ (What do you like doing there?) Offer a place you visit for a similar reason.
If an answer is too short to build on, use 例えば？ (For example?) or share your own example first. A short story gives the other person something concrete to ask you.