Just a personal note. Not to disagree with anybody, but I never liked feeling as if I were being interviewed (= grilled) in the name of conversation, and after a bit it would really start to irritate me, as if I were responsible for entertaining the well-meaning asker by being witty and interesting in response to whatever they thought up. It tends to make me clam up. (Yes, really.) And I don’t like doing it to others either. I always feel so phony plying someone with question after question. “What do you…do you ever…what’s your favorite…?” makes me want to say “Let me out of here!” Not that it isn’t a good method for some—oh my goodness yes, it is great for some—but I always want to have an alternative. And here it is, for me:
the leading observation.
Make it a pithy observation if you can, or enticing, intriguing, even brilliant if you can pull it off, but what it has to do is furnish an opening of some kind for a reply, without any pressure; be a conversation starter, not stopper.
What it is not, ever, is that it is not personal about the other person: you’re very tall, you have nice hair, you look like you enjoy the outdoors, you remind me of my sister-in-law (why do I remind people of their sisters-in-law, and what the hell am I supposed to say to that?) or my best friend in first grade. Never, not ever any one of those. Nor is it about yourself: I won a trophy like that once, I’ve read all the works of that author, I hate to read, I love this room, I wish I had a didgeridoo like that one.
Instead, here’s the movie scene to picture, so common it’s a cliche: the character—say a young woman—is standing in the host’s library or living room or conservatory or, hell, their garage, alone, holding a drink, and looking at something—a book, a piece of statuary, an artifact, a collector’s item, a tire iron, a photograph, a stain on the rug, who knows what—and the other character comes up behind her, sees what she’s looking at, and, as if he were reading her mind, says: ”—~—~—~—.” Whatever he fills in the blank with, it catches her attention, and now they are talking. About IT. Not about her or him or what movies she likes or what he does for a living. Takes off a huge amount of social pressure and allows them, as soon as they like, to start getting personal or even to start speaking metaphorically and suggestively about the thing, using language that symbolizes the mystery they’re both there to solve, or the secret one of them knows about the other, or their growing interest in each other, or whatever. That’s how it’s done in the movie dialogue. Without a script, it won’t work quite the same for us, but we can use the model.
If you have a lot of thoughts, ideas, and opinions of your own, or a broad education, or some wide general reading, or some specific strong interests and passions, or even just a head full of a movie you just saw, you can find some sort of connection to something in the environment and make an observation. It won’t put her on the spot. She can ignore it if she wants to. She can open up and tell you all about herself. Or she can just smile and ask you a simple question like “What makes you think so?” and now you are having a conversation. VoilĂ !