The first impression is crucial, and you want to make sure yours is intriguing and memorable. To help you with this, consider asking these questions, and check out this article for many more: What’s something that always makes you smile? What’s a fun fact about you that most people don’t know? If I were a flower, what kind of flower would I be? These questions will help you gain insight into the guy’s personality and interests while still keeping the conversation light and flirty.