Someone you know has had bad news. A death, a diagnosis, a marriage ending, a job gone.
You open the message thread. You type something. You delete it. You decide you will ring later when you have thought of the right thing, and then you do not ring, and after a fortnight it feels too late to say anything at all.
This is close to universal, and the people on the receiving end nearly all report the same thing afterwards: the silence hurt more than any clumsy message would have.
The thing worth knowing first
There is no right thing to say. No sentence exists that will make a bereavement better, and going looking for one is what causes the paralysis.
What a message can do is much smaller and still worth a great deal. It says: I know, I am thinking of you, you are not carrying this without anyone noticing. That is the whole job. A short message that does that beats a perfect one that never gets sent, by a distance.
Say something within a day or two if you can. If you have already left it three weeks, say something anyway. "I've been thinking about you and I didn't know what to write" is a complete and honest message, and it lands better than continued silence.
What tends to help
Name it plainly. "I was so sorry to hear about your dad." Not "your loss", not "what happened". People who are grieving are usually relieved when somebody uses the actual words rather than talking around them.
Say something specific about the person, if there is a person. One memory, one detail, one thing they did. "I still think about your mum making us all eat before we left the house" is worth more than any amount of sympathy in the abstract, because it is evidence that someone else holds a piece of them too.
Make the offer concrete. "Let me know if you need anything" puts the work on the person least able to do it. "I'm going to drop some food round on Thursday, I'll leave it on the step" does not require them to decide, ask, or be grateful in the moment.
Take the pressure off replying. A line like "no need to reply to this" is small and genuinely kind. Somebody in the middle of it may have sixty messages and no capacity.
Keep going after the first fortnight. Attention arrives in a wave and then stops, usually around the time the practical business is finished and the actual grief starts. A message six weeks later, or on an anniversary, matters more than most people realise.
What tends not to help
Silver linings. "At least he didn't suffer", "at least you're young enough to try again", "everything happens for a reason". Each is an argument that the situation is better than the person thinks, and it reads as a request to feel less bad in order to make the sender more comfortable.
Redirecting to yourself. "I know exactly how you feel, when my aunt died..." Some shared experience helps, briefly and offered lightly. A story that becomes yours does not.
Advice, unless asked. There is a strong urge to be useful by solving something. Solving is rarely available and is almost never what is wanted at the point of the first message.
Nothing at all, out of fear of the above. It remains the most common response and it is the only genuinely bad one.
Illness, redundancy, separation
The same shape holds with small adjustments.
For a serious diagnosis, avoid the war metaphors, because battles and fights imply that people who die from an illness did not try hard enough. Say you are thinking of them, ask how they are actually doing, and follow their lead on how much they want to talk about it.
For redundancy, the trap is reassurance that skips past the feeling: "you'll walk into something better" may well be true and is not what is needed on day one. Acknowledge that it is horrible first.
For a relationship ending, the trap is taking sides too enthusiastically. Criticising the ex feels supportive and becomes awkward if they reconcile, and it makes the person defend a decision they are still making.
The very short version
If you have read this far and still cannot start, use this and change the name:
I heard about your mum. I'm so sorry. I'm not going to pretend to know what to say, but I'm thinking of you. No need to reply.
That will do. It has always done.
Where the app comes in
Just to Say is a small collection of short lines for the moments when the words will not come — condolences, but also birthdays, anniversaries, thank-yous and encouragement.
You find something close to what you mean, copy it, and send it through Messages or WhatsApp. The intention is not to write the message for you. It is to get you past the empty box, which is where most unsent messages die.
Change the wording to sound like you. A slightly awkward sentence in your own voice beats a polished one in somebody else's.