Don’t feel like you have to jump straight into a search as soon as the first date starts. Deeper conversations will come more naturally when you have established a somewhat basic relationship between you.
When you arrive on a first date, try to start a casual conversation from the context in which you are. For example, if your date chooses the restaurant you’re in, ask him if he’s been here before, how he discovered the place, and what he likes about it. Or if you’re at a bar that specializes in bizarre cocktails, ask him questions about his drinks and share your own. You can also talk about what part of the city you are in and how much time you have spent in this area, an interesting article on clothing or jewelry on your date, or where they came from before meeting you.
From there, let the conversation flow naturally — maybe they’ll point out how hard it is to find good Thai places in the city you’re in, or a good friend who brought them here before, or how much they like to eat outside Pay attention, ask follow-up questions and offer your own thoughts or stories that relate to your date just shared.
Some people refer to this type of conversation as “small talk,” but the key to making it feel lively and interesting is actually leaning towards any opportunity to start sharing what the other person is sharing and unique details about yourself. These early revelations and early relationship-builds will oil the gears so that the following conversation will feel easier and more normal.