Your waiter is not paid to be your friend. Yet so many people feel the need to forge a personal relationship with their servers. Despite your innocent intentions, soliciting the staff for personal information can be inappropriate if you ask the wrong way. You do not have a right to know facts about your waiter or bartender just because they are indentured to you for the evening. The dynamic is a lot like prostitution. We are paid to act like we like you. Sometimes we do, sometimes we don’t. Most of the time we don’t care. It’s business not pleasure. Unlike prostitutes, waiters have the misfortune of getting paid after the sex which gives the John a lot of power. If you want your server to like you, you won’t abuse it. 
The equation is simple: you have needs, we try to anticipate them. You are hungry, we can help you get food. But do you really need to solicit information from us about our private lives? In theory, you are humanizing us by displaying that you see us as more than just a servant. In reality, you are intruding in a way that can be dehumanizing by exposing our vulnerabilities and the lopsided dynamics that come along with being your bitch. Asking about our personal relationships, romantic affiliations, aspirations outside of work, school plans, birthplace or nation of origin doesn’t make us feel like you care. It only puts us in an uncomfortable situation if we prefer not to answer. Especially since you haven’t paid. Until the check is settled, any unsportsmanlike behavior on our part may jeopardize the tip. Only the most offensive behavior on your part will result in our sacrificing a gratuity for pride. So, for self-preservation, we may endure your insinuations to protect ourselves from getting stiffed, but you will not get your desired response. Keep the focus on food and beverage first before you attempt to get to know your server or bartender. You have a much better chance of connecting with us if you make it a conversation where we feel our autonomy is respected. Firing intrusive questions our way while we’re trying to work, on the other hand, will make us disengage even more.