You can start by asking questions, and try to start small—try these funny first date questions. Ask them about their day and or what shows they’re watching. This can help put them at ease and get them into the groove. As things move on, that is when you can get a bit more personal. You can ask about things like their family or their plans for the future. At this point, you should try to learn more about who they are. Politics and religion can be touchy subjects so tread lightly. Wait until the end of the night before asking about a second date.