Something bad or unfortunate has happened to someone you know. Here’s what you say. You say:
“I’m so sorry. I can’t imagine how difficult this is. I’m just really so sorry.”
If you can go the extra mile and send flowers, drop off a lasagna or offer a shoulder to cry on over high-quality whiskey shots or drinks featuring artisanal ingredients someone made up in Brooklyn just last week, great. If that is not appropriate – because you are uncomfortable with emotion or marinara sauce or giving 1800-flowers $75 for some tulips you could get at Trader Joe’s for $20 – that’s fine. You have added to the sum of kindness and courtesy in the world and your work is done.
In case you had any second thoughts or objections to that course of action, here are the answers to those:
1. “I’m not sure what exactly to say so I’m going to avoid the whole thing and say nothing.” Most people don’t say this in as many words but act like they did. Stop it. Just stop. The only truly bad option is to say nothing. Silence is the kind of thing that is remembered, not awkward phrasing.
2. “I’m pretty sure I’ll say the wrong thing or in the wrong way, and that’ll be worse than saying nothing.” No. That is incorrect. However profound your fear of saying the wrong thing, see above: there is nothing you can say that will be as wrong as saying nothing. Unless you are just a terrible, offensive person. Which you aren’t. We both know you’re not. So be a mensch already and say something nice.
3. “S/he is a really a private person and I don’t want to intrude.” Respecting people’s privacy is admirable but overrated. (Unless you are talking on a cell phone in Starbucks, in which case you should seriously fuck off already and respect everyone’s privacy because this is not your living room.) I am a private person and have been on the receiving end of many explanations of why I was deemed too private, too calm or too competent for someone to reach out to me, and here is my answer: compassion is always welcome. I and my kind may not choose to confide in you beyond saying, “Thank you,” when you are nice to us, but your effort is noted and appreciated.
4. Do not be nice to someone having a hard time and expect that s/he will then confide in you. This is not Oprah. No one is walking away with the answer to all their problems or a Pontiac. Try to tamp down your expectation of any particular response or resolution. The nature of having a hard time is that everything is weird. Any response is fine.
5. If that response is weeping and telling you the whole story from the very detailed beginning, it is OK to just listen. You do not have to fix this (and you can’t, even if you tried). It’s also OK to have your own limits and set them calmly and firmly, like excusing yourself for a voluntary root canal. Pre-planning a simple exit like this is fine.
6. Even if you think you can imagine how hard this is, even if you have been through something you believe is very similar, do not bring it up. Every disappointment is a unique (if unfortunate) flower. Commiseration and comparing notes will come later (at his/her discretion). The universality of pain and/or recovery is likewise not relevant right now, so keep that to yourself. Phrases to avoid: “We all suffer,” “This too shall pass,” and anything beginning with, “My brother-in-law…”
7. Do not assume that everyone already has someone to say kind things to them or that they can be heard enough. You never know. Erring on the side of generosity is always the better choice.
In short, “Do unto others,” etc. If you were in her shoes, would you want a kind card? A supportive word in passing? To be told that you are thought of when things are hard? Yes. Yes, you would. So let’s all make a pact right now that we will step out of our days, our concerns and details, our, “I am really so very busy…” and, “I wouldn’t know what to say…” and just say it anyway. It matters.