Whether you’re on a date or just talking to the cute guy you always see in the elevator, the key to keeping a conversation going is to ask thoughtful follow-up questions. So, when someone tells you something — anything — listen intently, and then respond with a question that elicits a deeper explanation about what they just shared.
For example, if someone mentions they love the summer, ask what they love about it. If they tell you they’re having a rough week, ask why that is. If someone mentions they’ve been playing video games all day, ask what game they’re playing and what’s so fun about it. You can even go a level deeper: Do they consider themselves a serious gamer or a casual gamer? What’s the first game they couldn’t stop playing?