"I'll put it in a message"

Once you've accepted that the thing has to be said, the next temptation is to write it instead. You could send a long text, an email or a letter left on the kitchen table. It seems to solve everything. You get to choose your words and say it all without being interrupted, and you don't have to watch their face.

I understand the appeal, and I'd steer you away from it for anything that matters. There are three reasons.

The first is tone. Justin Kruger, Nicholas Epley and colleagues ran five experiments on how well people convey tone in email. Senders wrote messages with a particular tone in mind, such as sarcasm or humour, and predicted how well readers would pick it up. They were consistently overconfident. The writer hears their own voice as they type, with all its warmth and emphasis, and can't easily imagine the message without it. The reader gets bare words. In a difficult message, the bare words are nearly always read as colder and angrier than they were meant. The sentence you wrote gently gets read in the voice the reader fears.

The second is that a message can't adjust. Face to face, you see within two sentences that they've misunderstood, or that they're hurt, or that they already knew. You change course, and soften, and clear up the misreading before it sets. A message delivers all eight paragraphs regardless, including the six that turned out to be unnecessary and the one they'll reread forty times.

The third is what happens next. After a message there's a silence, which you spend imagining their reaction. Then comes a reply, which has been composed with as much care and as little tone as yours was. The two of you can exchange careful documents for days, each one slightly more hurt than the last, without ever having the conversation. A message also lasts. It can be reread, quoted back to you, and shown to other people.

So for anything important, say it aloud. In person is best. A phone or video call is next best, and it's the sensible choice when you live far apart.

Writing does have two good uses, and I'd encourage both.

One is to book the conversation. "There's something I'd like to talk about, nothing terrible. Are you free Thursday evening?" A message is ideal for this. It's short, its tone is hard to mistake, and it means the other person doesn't arrive unprepared.

The other is to prepare. Write the whole thing out, as long and as angry as you like, in a document nobody will see. It clears your head and shows you what you really think. Reading it back the next day also helps you find the one thing in it that matters, which the next chapter will need. After that, don't send it.

There are exceptions, and they're mostly about safety and power. If you're dealing with someone who twists what was said, or with a formal matter at work where a record will be needed, then writing protects you, and you should use it. If speaking face to face doesn't feel safe, the preface and chapter 15 apply. And some people do express themselves far better on paper. If that's you, consider writing your first two sentences and reading them aloud. It's allowed. "I've written down what I want to say because I wanted to get it right." People are usually touched by that.