You may think you’re showing a polite interest, but some questions will rub a person the wrong way: “So do you have a girlfriend yet?” “When are you two going to get married/start a family?” “Didn’t you give up smoking?” “Can you afford that?” “When are you going to get a real job?” Show an interest with more open-ended questions, like “What are you up to these days?” or “What’s keeping you busy?”