Sounds like you're instigating something called "the interview". This is a conversation where one interrogates the other person - how old are you? where do you live? how many siblings do you have? bla bla bla. It's very one sided, and not a good way to start a two-sided conversation.
Try to identify something nearby, and comment upon it, ask what they think. Like in a cafe - "i'm thinking about ordering x, what are you thinking of ordering?" then talk about food. Bad example but you get what I mean.
Try talking about sports, hobbies, favorite vacation spots, food, music, etc ... And I said TALKING not asking. When you ask too many questions it can make the guy feel like he is being interrogate (and you can kiss your second date goodbye) but on the other hand if you engage the conversation by bringing something fun to the table and make some pauses so that the other person can actually bring something to it.
By doing this no one FEELS interrogated and you won't feel like you are always asking the same questions over and over again (even if its true..lol) unless you are infront of someone who has nothing to talk about.