When I have my professional hat on, it's easy—and important—for me to feel genuinely curious about what’s going on in someone else’s life. But in established relationships, I realize that I often just make assumptions and am lazy. And self-serving.
It's hard to pretend that we don't have history with someone that we have history with! But asking questions is still the best way to find things out, even with people we think we know really well. (Who knew?)
It's important to remember that our perceptions of the people in our lives will have varying degrees of accuracy. We might be highly intuitive about people, but thoughts and feelings can change in a moment. Why should what someone said yesterday or five years ago form your opinion of them today? And what about the language we use? When someone says "a lot of difficulty" or "really happy" or "totally awful," what does that mean to them? We keep each other at arm’s length when we make assumptions about meaning and form judgments based on those assumptions.
Being curious means not only asking questions (kindly and gently), but also asking for clarification about meaning. No, it's not terribly efficient. It might even feel like reinventing the wheel sometimes. But it can open up a really satisfying dialogue with the people in your life. Some interesting things might even take place: less jumping to conclusions, less rumination, and maybe even more intimacy and compassion.