Don’t feel like you have to jump right into an inquisition as soon as a first date starts. The deeper conversations will come more naturally once you’ve established a bit of a foundational rapport between you.
When you first arrive on the date, try starting with a little bit of casual conversation drawing from the context you’re in. For example, if your date picked the restaurant you’re at, ask her if she’s been here before, how she discovered the place, and what she likes about it. Or if you’re at a bar that specializes in quirky cocktails, ask him questions about his go-to drink and share your own. You could also talk about the part of town you’re in and how much time you each have spent in the area, an interesting article of clothing or jewelry your date has on, or where they came from prior to meeting up with you.
From there, let the conversation flow naturally—maybe they’ll bring up how hard it is to find good Thai places in the city you’re in, or a good friend who brought them to this spot before, or how much they love eating outdoors. Pay attention to what comes up, ask follow-up questions, and offer up your own thoughts or stories that relate back to what your date just shared.
Some people refer to this category of conversation as “small talk,” but the key to making it feel vibrant and interesting is actually engaging with what the other person is sharing and leaning into any opportunities for you both to start disclosing unique details about yourselves. These initial disclosures and early rapport-building will oil up the gears so that the following conversation will feel much easier and more natural.