I really have come to believe this is covered by the Woody Allenism "90% of life is just showing up." Being there is more important than what you say.

I agree with dhartung: being present for the person is crucially important, but tone is good to master if you can. Tone helps you avoid silencing the person who needs to vent, or pressing the person who wants privacy.

I often go with something in between your two modes, Firas, with an addition: "Aw, I'm so sorry, that sounds like it sucks" with an optional "do you wanna talk about it?"

This gives the person a chance to define how much it sucks, or to tell me how it doesn't really suck, or to expand on how very, very much it sucks. It also indicates that you're a willing ear, that they should feel free to vent, that they should feel free to decline to discuss it, whatever.

For written communication: I can remember verbatim a phrase that an acquaintance used in email. I had messaged him to explain my absence, and mentioned that I would be tied up for an unknown time, because my father had entered home hospice.

My mere acquaintance emailed back, "That sounds hard. If you want to talk about it, or not talk about it, or just freak out with someone, let me know." It was the kindest, most open-ended, most accepting thing anyone said to me in a long time.

I know that phrasing won't work for most situations, but the essence is there. It let me determine the scope of my reaction, it indicated that he knew grief was hard and unpredictable and that it makes people act nuts, and that that's okay. It made me want to get better acquainted.I am now married to that acquaintance.

A couple words and a simple hand-clasp are generally appropriate.

Listen. Don't be concerned with how you're coming off. It's not about you. (This is the most common mistake people make, even though it's rarely out of malice or narcissism.)

All good suggestions so far, i think. I would add the same but in my own words, "Simply bare witness to the other person's experience." Saying, for instance: "I can hear/see how sad, frustrated, angry, etc this is making you." Then just leave the opening for the person to continue.

And later, maybe, "What can you do about it?" Or, "what do you need to do to make this a better situation for yourself/the other person?" And, "how can I help?"

Also, I should say I don't have a care about the above response being too familiar. If they've come to me, I'm on tap to simply be there for that person.

Listen. Don't be concerned with how you're coming off. It's not about you.

I agree with this, but very often in a crisis, the peripheral people make it clear that it is about them; often, it's about their inability to acknowledge another person's crisis.

But I suspect that we agree on the crux of this: if you're there, and you're willing to listen or to let them be silent, you don't need to worry too much about your tone or your specific word choices.

I would say it's simple: don't minimize the crisis, don't try to define their experience, and don't dwell on it if they're not dwelling on it.

One of my hospice co-workers was talking about a conference she heard in which the person said that grieving people should make a list of their friends, divide them into Doers, Listeners, and Respite -- that is, people who are good at doing something to help, people who are good at listening, and people who aren't good at listening or doing helpful things but are great for fun or distracting stuff. The griever can then kind of figure out what they need in a given moment and contact a person who is good that, rather than doing what many of us do and trying to, for instance, force someone who's a doer into a listening role or wheedle a respite-y distraction person into a helping doing role. But it's also a way of saying that all three roles are important.

I think Elsa's example is so great because it hits all three of these, but also also because it lays out what the person is capable of and comfortable with doing to help the person. I think if you can lay out what your strengths are, to some extent, and offer those skills to the person, it's good. So:

"I'm happy to listen if you want to talk about it."

"Please let me know if there's anything I can do to help. Do you need X, Y, or Z done?"

"Wow, that sucks. If you need a distraction, I'm doing X later, if you want to come along?"

Or some combination of whatever of those feels right.