Dating is like an intricate dance. You learn about him, and he learns about you. Dating questions for him can help you scratch more than just the surface. Explore his past, present, future and personality through 21 online dating questions to ask him. For more fun, make it a game. Learning about someone's past can be tricky; you don't want to seem like you're giving them the third degree, but at the same time you want to know more about them.