Pretend, for the length of this entry, that you host a small, gentle talk show. Long conversations, not soundbites. Whoever you'd most want to sit across from — dead or alive, famous or known only to you — is welcome.
The first guest sets the tone for the whole show. Who deserves it?
Choosing a first guest exposes the questions you've been carrying around without realising. The conversation you'd most want to have is, in disguise, a question to yourself. Often you can begin to answer parts of it without the guest, just by writing what you'd ask them and imagining what they might say back.
Lovely on a Sunday afternoon, after a documentary or biography, or any time your curiosity feels under-fed. Also useful when you've been doing a lot of small talk and miss the deep kind.
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Name one guest, not a wish list.
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Explain in one sentence why them first.
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Write three questions you'd actually ask.
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Imagine the answer to one of them.
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Ask what this guest would notice about you in return.
Other ways to ask the same thing
“Who's the first person you'd want at your imagined table?”
“If you could host a single deep conversation, who would you invite?”
“Which voice do you most want to spend an hour listening to?”
It's tempting to pick a celebrity for the prestige of it. If they're honestly your answer, great. If they're a placeholder, look again. Sometimes the truer answer is a grandparent, a former teacher, or someone who'd never expect to be invited.
My grandmother. She'd be furious to be on a show, then she'd settle and tell stories better than any of the people I'd considered before her. I'd ask: 'What did you really think during those years no one talked about?'; 'When did you stop being afraid of your own opinions?'; 'What did you want for yourself that you didn't get?' The last one I can almost hear: a long pause, then a small laugh, then 'a quieter husband and a louder life.' She'd notice that I'm still tired, and she'd tell me to sit down.