So what are some intelligent questions to ask guys? (I'm getting tired of asking how many siblings and pets he has!)
Most Helpful Guy
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.0