How to Write a Letter to a Stranger

Some Tips for Beginning a Conversation

This is the second piece in a series of two, on the art of letter writing. Last week, I wrote about why I think we should write more letters. Today, I’d like to talk about how. A version of this piece first appeared in Areo Magazine here, in the context of a letter-writing competition I was helping to promote. It’s focused on how to write to someone for the first time.

Appearances are against me. Don’t believe them. I have written you in intention fifty letters.—Charles Dickens, letter to Lady Blessington, 1844

There are no hard and fast rules for writing letters. There’s no fixed format, no prescribed style. If you find it easy to compose missives and your correspondents enjoy hearing from you, don’t change a thing. But I’ve heard from a number of people who feel daunted by the idea of composing an informal letter—a form of writing rarely practised nowadays. So here are a few suggestions for those who find themselves staring listlessly at a blank page or screen.

Focus on the Recipient

A Letter always feels to me like immortality because it is the mind alone without the corporeal friend.—Emily Dickinson, Letter to Thomas Wentworth Higginson, June 1869.

Writing teachers often advocate constructing an essay around a thesis statement, followed by an introductory paragraph outlining the question you wish to address in more detail, supplemented by three to four paragraphs of exposition, with examples or points of argument and rounded off by a conclusion, which draws all your material together in support of a specific case. I’m not convinced that this is a good model even for an expository essay. In a personal letter, it would be disastrous. This might be a useful schema for a few very specific types of correspondence, such as a letter to a newspaper editor—which is often simply a short essay in epistolary masquerade—or an exploration of a philosophical or scientific topic in letter form.

But, in most letters, we should jettison this entire scaffolding. A letter should not be a watertight construction, an impregnable fortress. It should be an opening offer that invites negotiation. Most letters should be written with the goal of eliciting a response. For that, we not only don’t need to marshall all our arguments, we shouldn’t. A letter is not a standalone piece, but part of an on-going conversation. Instead of the equivalent of an article, think of it as the kind of brainstorming session you might have with a friend, before you begin assembling that article. Settle down in a comfy chair, pour a glass of wine, try to visualise your correspondent and imagine you are chatting to them.

Your main aim should be to write something that your correspondent will enjoy reading and feel eager to respond to.

This is one of the letter form’s greatest strengths: you don’t have to second guess who your audience will be; there’s no requirement to try to please everyone. When you know exactly who you are speaking to, it’s easier to resist both obscurantism and pomposity and their opposite, dumbing down. This puts the emphasis squarely on communication and can free you from some of the self-consciousness that so often hampers writers in other genres. The temptation to grandstand is greatly reduced when your reader is not a conveniently docile figment of your imagination, but a real person whose furrowed brow and single raised eyebrow you can easily envisage, as you write.

Begin Simply

I have begun this letter five times and torn it up five times.—James Baldwin, “A Letter to My Nephew” 1962

Beginning the letter is, for many people, the most daunting hurdle. The computer screen sometimes seems to stare back at me in disdain, daring me to pollute its pristine whiteness with my puny black strokes. If your blank screen is as merciless a tyrant as mine, get those opening words down as quickly as possible. Keep it simple.

Perhaps the easiest way to begin is to explain why you have chosen to write to that particular person on that specific topic. Be as clear and brief as possible when you lay this out. Don’t be afraid to state the obvious.

You could start, for example, by citing something your correspondent has published elsewhere, which has inspired you to write. Here are a few gambits I’ve used:

—I’ve recently finished reading your book, Why Are We Yelling: The Art of Productive Disagreement … Anxiety is one of the most frequently evoked concepts.

—Your book, A Self-Portrait in Black and White: Unlearning Race knocked me for six and I’m still reeling. (I have published the resulting correspondence here.)

—You are one of the most intriguing people on Twitter. … A few days ago, you wrote something so utterly you that I think it can serve as a perfect example.

You can also outline an interest or situation you have in common, on which you’d like to compare notes. Here are some openings other people have used:

—I am writing this letter because we both are developing arguments about how existential meaning, what you call “meaningness,” has become increasingly problematic for people today.

—I think we could have a productive discussion about our respective views on the issues of growth, progress and sustainability.

—I’m also a passionate dancer, like yourself …

—we both now have multiple children … I wanted to discuss schooling …

Many letter conversations begin in other formats, in which case it’s helpful to provide a quick reminder of that context and summarise the discussion to date. Think of all those business emails which begin “following up on our conversation of this afternoon,” “this is in response to your email about x,” “as requested, I’m sending you details of y.”

—We recently spoke briefly about truth, reason, and rationality

—During our discussion on Embrace the Void, we touched on the metaethical topic of Moral Realism.

Incorporate the Personal

A writer—and, I believe, generally all persons—must think that whatever happens to him or her is a resource—Jorge Luis Borges, interview, ca. 1981

A letter is more personal than an essay and it therefore feels more natural to show how your personal experiences have influenced your attitudes and beliefs. You can encourage your correspondent not just to understand your ideas, but to empathise with you, as you retrace how and why you came to hold them.

This has the added benefit of demonstrating that, on most topics complex enough to inspire a letter exchange, there are a range of possible views. Most things cannot be decided using formal logic or listening to the voice of moral intuition.

We inhabit specific memetic environments, in which we may be exposed to good arguments for one side of a case and poor ones for another. We are swayed by the examples we’ve personally encountered; by how things impact our own lives and those of our friends; by local customs, expectations and etiquette—and the local here encompasses not just geographical location, but the landscape of the mind: our favourite books, teachers, pundits, podcasts, news media. Ideas take shape in the ecosystems of our brains and both adapt to and change that mental environment. We constantly rearrange them to fit, like parts of a sliding tiles puzzle.

And our experience, of course, influences what we think is more attention worthy, more valuable or more dangerous. This is why, for example, I respond with so much faster raised hackles to the Hindu right than to white nationalists: exposure has increased my number of antibodies. But, as with the immune system, we can also have over-reactions, allergies to perceived threats that are not actually harmful.

Letters encourage intimacy across geographical distance. They are attempts to bridge a physical gap with words, to let a person’s voice stand in for them, in their absence. With their personal format, they invite us to welcome someone else into our mental world, to give her a behind the scenes tour. In an essay, we present the finished embroidery to the world. In a letter, we turn the cloth and show how the individual threads were stitched, leaving the ends dangling, so that the correspondent can, if he wishes, tug gently at any one, and see how far it unravels.

Organise Your Thoughts

When we try to pick out anything by itself, we find it hitched to everything else in the Universe.—John Muir

A letter should convey a degree of spontaneity, but it shouldn’t be a stream of consciousness. The ideal is to write something that can readily be replied to and that involves separating out your different strands of thought.

Unless the letter is very short indeed, always divide it into paragraphs and err on the side of more paragraph breaks, rather than less. Some paragraph spacing will give the eye a sensation of respite, even if the missive contains one single, extended thought.

Digressions, anecdotes and literary allusions can all add colour and character to your writing—but don’t lose sight of this main idea, which is to inspire a reply. If you aren’t interested in how your correspondent will respond, you should probably be framing your thoughts as an essay instead.

You and your addressee are like two partners, embracing in a dance. Don’t try to shine as a solo act: correspondence is a joint endeavour. Think of it as having a call-and-response structure. Model what you hope to receive in return. Provide the level of detail, the number of arguments, the degree of frankness, the warmth, empathy, civility and care that you would like to elicit—and that you think your correspondent can reasonably be expected to supply.

If your letter is an answer, begin by briefly recapitulating some of the letter that you want to respond to, perhaps by summarising what you felt on first reading it. It creates good will when your correspondent feels you have perused her missive carefully. If appropriate, mirror the structure of the letter received, responding to each paragraph with a paragraph of your own, each anecdote with a story of your own. Or, if you prefer, choose just one, crucial part that you want to elaborate on or dispute. It’s often especially effective to single out a sentence or two, quote them and discuss whatever is striking about your correspondent’s specific word choices. If there is a turn of phrase that leaped out at you as you read the original, it’s worth examining. What does it suggest about her ideas? How might you have put things differently?

Borrow

All ideas are second-hand, consciously and unconsciously drawn from a million outside sources—Mark Twain, letter to Helen Keller, 1903

A quotation from literature can summarise how you think or feel on a topic with more vividness and clarity than you could express in your own words. Before writing anything that is important to me, I always spend some time searching my favourite authors, to see what they have had to say on the topic—one of the many joys of the internet is the ease with which this is now possible, even if you don’t have an encyclopaedic memory and a library of books, stripy with underlinings and crested with a fan of lemon post-it notes, marking the many places you promised yourself to revisit. Books that used to take a day to order are now available with a single, brief ten-fingered tap-dance across my MacBook keys. Even if you don’t end up citing any of the nuggets you find, this is likely to inspire you and give you a sense of the expansiveness of whatever subject you’re contemplating.

Be sparing with this kind of extrinsic material, though. Your quotations should be relevant and it should be clear, both to you and your reader, why you have chosen to include them. Just as paintings are generally best viewed framed by an expanse of empty wall, a citation from literature will be more powerful when it’s not jostling for attention with a dozen others.

End on a Generous Note

When once you have said your say, fully and clearly, on a certain point, and have failed to convince your friend, drop that subject: to repeat your arguments, all over again, will simply lead to his doing the same; and so you will go on, like a Circulating Decimal. Did you ever know a Circulating Decimal to come to an end?—Lewis Carroll

At the end of your letter, you are handing over the baton. If you’ve covered a wide range of topics, it might be helpful to summarise them before you sign off and condense them into a single question, which your interlocutor can use as a cue. Don’t overwhelm your correspondent, leaving him wondering how to even start to respond. Give him a prompt, suggest a topic for the reply, ask him to enlarge on a specific question you’ve touched upon.

It’s gracious to give him an alternative, too, an out.

If you worry that you may have bombarded your interlocutor with inquiries, suggest, perhaps, that she select the point or points of most interest and respond to them alone. It’s her turn to steer the conversation. Like a good lover, plant suggestions, don’t attempt to corral; seduce, don’t coerce. The exception to this is when there is a central issue that you feel must be addressed: in which case, be clear and direct. Insist the elephant’s presence is acknowledged.

If you are the one who wants to bring a lengthy correspondence to a close, be polite but explicit about this. Recapitulate your points of commonality and disagreement, thank the correspondent for what you’ve learned and for the gift of their time, the most precious commodity of all. Take a moment to reflect on how the letters have impacted you, changed your mind or enriched your understanding. And then simply acknowledge that you’ve expressed everything you needed to at this time. “No man is always in a disposition to write,” Samuel Johnson advises a correspondent, “nor has any man at all times something to say.”