10 Questions to Ask a Friend or Loved One
1. What are your dreams? Sit down with a cup of coffee--or a glass of wine--and allow some silence. Smile warmly. Ask this question with no elaboration--don't mess it up with other words. Then wait.
2. What would you say has been the happiest day of your life? (and, Why did you choose that day?) Think of this question as the start of a much longer conversation. Why did they choose that particular day? What other days have been happy ones? What is happiness, for them, anyway? Is it the same thing as joy or contentment? Allow an hour at least!
3. Can you tell me about your plans? We are all so FULL of our own plans. Our own priorities. Our own goals. Our own stories. Ask this about anything: The other person's career, their upcoming vacation, their weekend. Instead of talking about your plans--or what you think the other person's plans should be—ask this question and just listen.
4. What do you think about...(this idea, news event, etc.)? You'd be surprised how many people are never or rarely asked these four words. They can unleash a marvelous conversation--and help you make a warm connection.
5. What do you wish you could spend more time on each week? Less time? I like this question because it gets the other person talking about what they really love and enjoy in their lives. And I get to know them so much better after they answer.
6. Can you tell me something about yourself that I don’t already know--and that might surprise me? This question can reveal surprising, even astonishing things about someone you thought you knew well. A friend of mine once answered this by telling me "I spent a night in jail in Lubbock, Texas." Someone else said, "I rode on Air Force One with President Lyndon Johnson." Yet a third revealed they had been jilted the day before their planned wedding!
7. Right now, what are you most passionate or excited about in your life? This is what I call a "Passion Question." When you tap into people's passions, they come alive and the conversation comes alive. All of a sudden you're not just chit-chatting about mindless trivia. You're talking about the stuff that lights us on fire!
8. What would you say gives you the most fulfillment in your life? This comes at passion from a slightly different angle than the previous question. Maybe the answer will be the same. Maybe not. But a conversation about what fulfills us in our lives is always a rich and rewarding one.
9. What are you doing this week that I could help you with or support you on? Even if the answer is nothing, you'll make the other person feel supported and loved. If there is something--well, it's a good day when you can identify how to help someone else. Remember, "from everyone to whom much is given, much shall be required." Maybe you can run an errand for your spouse. Or help a friend with an unpleasant task. It could be that simple.
10. Can I share with you the reasons why I love you so much? (or, value you so much as a friend?; or, enjoy spending time with you?; or, am so proud of you?; etc.) Think this one through beforehand. Really ponder it. One of the greatest gifts you can give someone--a spouse, a child, a friend--is to share with them why you think they are so special. Why you treasure them. Why you love being around them. This one is powerful--go for it.
