I can't think of a single time when it would be appropriate to say "Be careful" to someone

"Be careful" often comes across as condescending (like you don't trust them not to be behave sensibly in this situation where it is bleedingly obvious that care ought to be taken - it suggests you think they're stupid or irresponsible). And when it doesn't, it's pretty much just a tiny flash of fear into their hearts. Like, "remember someone might attack you! imagine that for a second before continuing with your walk". That's not a nice thing to do to someone.

People say it to people who are about to go on holiday and that is... what are you doing? They are trying to have a nice time and take a break. Tell them to have fun!

It's also, obviously, completely ineffectual. No one every changed their behaviour in response to the words "be careful".

Here's what to do instead:
If you are genuinely concerned they are not aware of the risks and won't take appropriate cautionary measures (e.g. if they're a child, or it's an unusual risk that not many people know about). "Be careful" is useless and un-actionable - tell them what actual things they should do. ("Cook the blue-turning mushroom for 20 minutes before you eat it" / "the rocks are slippery here" / "that glass is gonna fall, move it to a stable surface!" (people tell me this pretty often and I always appreciate it).

More often though, "be careful" is about the person speaking, and you're saying it because you feel anxious and saying it makes you feel better. I think that is completely understandable! But since it is either condescending or puts a little bolt of fear into this person you care about, my advice is - say what you actually mean. It's probably one of the following things:

"I love you" (subtext: and so the idea of anything happening to you scares me)

"I'm feeling worried about this - can you reassure me?" (the difference is that it acknowledges that it's about you, not about them - it's not condescending because it doesn't imply that you think they're not taking obvious precautions, and it's less fear-inducing because you're framing it as a 'you' thing not a 'reality' thing. Which is largely correct - most of our 'be careful' fears are wildly disproportionate to the risk). I think you can even request specific actions that would make you feel better (calling a taxi, texting you when they get home) if you frame it as asking a favour of them to help you manage your anxiety. (They might say No, but you can ask.)

The underlying principle here is just honesty - actually say the true thing you're feeling, rather than giving instructions to the other person. Take responsibility for your own emotions (which doesn't mean you can't ask for help with them.)

And look, if they do die from whatever this is, would you rather the last words you said to them were "be careful" or "I love you"?

Note that if this seems un-workable because wouldn't be appropriate to say "I love you" or "please reassure me" to the person - for example, because they're just a co-worker and not a friend or family member - then it isn't appropriate to say "be careful", which has strong paternal/maternal vibes, and definitely not appropriate to ask them to help you manage your emotions.

So just stop that, stick to "have a nice night" or whatever.

This piece was originally published in The Whippet #80 – subscribe to get the next one in your inbox!