Questions to ask a guy during online dating. What's the biggest goal you're working on now? World News. How discretionary time is used says a lot about a person. Are you an adventurous person? Do you read reviews, or just go with your gut? Sometimes they lead to burning love sometimes they go down in flames. Let the questions follow each other naturally as the conversation unfolds. Someone who can think ahead is very attractive indeed. Perfect for a special date — or just a rainy day! What is something you are financially saving up for?