How to ditch the small talk

Not all small talk is bad—but when it's all you're ever engaged in with a colleague, friendly acquaintance, or even a distant friend, it can feel really meaningless. Having better conversations can strengthen bonds and also simply increase enjoyment for all parties involved. What are your go-to questions for getting into more meaningful conversations instead of small talk? I'd also love to hear thoughts on how to catch up with old friends you haven't heard from in a long time—for instance, someone who's just messaged you asking, "How are you? How's life?" on Instagram. How do you meaningfully connect with them instead of just saying "good" or another plain response that we're so accustomed to giving?