For a first date, whether in-person or virtual, a good rule of thumb is to treat the conversation like you already know the person, and you're just jumping back into an already existing discussion. If the chemistry is there, over-planning can sometimes suck that dry, so give yourself permission to just see what happens. Conversation is much more fun when it emerges out of the situation, so ask about things you can see in the background, what your date had for lunch, or what the view from their window is like. If you must, think about a few things you'd like to know about this person and write down topics, not questions.