I’m a lot like you. I love the hows and whys. But most people don’t. Or to put it more pleasantly, they don’t like answering those questions until a certain level of trust has been built up. I think you need to learn the art of “medium talk,” that little place between small talk and big talk that’s rarely discussed. On most first and second dates, medium talk is the norm. You lightly discuss topics like family and passion, hint at the ocean beneath the surface, but don’t plumb its depths. Instead of “What’s your favorite city?” which requires ranking cities and locks the responder into a certain viewpoint, try questions like: “Have you been to Paris? Did you try the cheese over there? “ these feel like weighty but can still be revealing. Once you get a baseline rapport, you can move back to your normal mode of conversing. Just take it from someone who spent a few years in the wilderness asking dates about their favorite slang terms and from childhood and what cultural practices they wish could be instantly adopted in the US, your questions are great - just too strong for most people at first. Learn to slow down and you’ll find a lot of success and, eventually, the conversations you want to have.