Want to impress your date within the first few minutes of meeting them? Use these 20 perfect first date conversation tips to do just that and more!. It can be awkward to run out of things to talk about on a date. It can be even more awkward to have the same conversations you've had on every single date. The key to having a positive experience is relaxed conversation, and that can be helped along with some well-chosen first- date questions. Before we get to. Conversation, however, is the spice that determines if you're a bland dish of blah but without some conversational panache, a first date feels pretty much like a. Stumped on what to talk about on a first date? Here's a list of 40 foolproof first date questions that are actually good and guaranteed to get conversation started. Have you ever had trouble finding something to talk about with someone you're dating? The evening can get a little awkward when the conversation runs dry.