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How do you respond to someone sharing bad news/situations?

I just stay quiet. I don’t like to say I’m sorry because that doesn’t feel genuine -its not my fault. I also struggle with faking concern when it’s a total stranger. I want to edit: I am not necessarily referring to like “my dad just died”. I mean like a conflict between two people where one is hurt. It doesn’t involve me, from my perspective the situation is dumb. But I am expected to at least go “I’m sorry you are dealing with this” even though it’s like… but it’s not my problem. And then I think well, how would I want someone to respond and I think unless I am asking for advice I would just want a listening ear, I don’t want them to talk at all. But people don’t seem to like that either even if they don’t ask for advice. What do you say when someone tell you bad news?
I’m taking the same class as one of my friends, but they are failing really badly. I want to be supportive of them when they tell me about their grades. All I can think of is “damn I’m sorry”. What could I say to comfort and support them? I find it difficult to respond to people giving bad news about themselves (i.e. A relative passing, a breakup, or general sad things in someone's life). How do I respond to these types of things, and maybe lift their mood? Don't put someone in the position of comforting YOU over THEIR difficult news.
Why don’t I feel immediate sympathy when I hear bad news?
I have a delayed reaction when someone tells me their bad news. It happened twice so far this week. First, it was when my coworker said her cat died over the weekend. I said “oh.” That’s it.
How do you deliver bad news?
I am currently on rotations and I was asked to deliver some bad news to a family. I had no idea how to go about it, and I was uncomfortable the entire time. I felt like I had no clue what to say, and I tried to be as direct as possible, and then listened to their silence. I offered to come back in a few minutes to give them some time. They seemed appreciative, but I would really like to be better prepared to do this in the future, so any advice is welcome.
Then, today, a customer at work said his wife passed away last week. I said “Aww no.”
Both times I was left somewhat speechless. It’s not til hours later that I realize I should have said more, like the typical “I’m sorry for your loss” or “I’ll keep you in my prayers”
My daughter got diagnosed with sone medical issues. Have to have minor surgery next week to determine how bad. I can’t sleep because all I can do is worry about what the results will be. How do I stop worrying? Also, this means that for the rest of her life she is going to have health issues. I feel so bad for her and her future issues. It isn’t fair for a small child to have to deal with this.
What’s wrong with me?
Example: ask friend what his spouse is up to and find out they're getting a divorce? Don't flip out and fall all over yourself apologizing. This puts your friend in the position of comforting you and appeasing your guilt and discomfort for something that would otherwise be completely normal (i.e. asking after their spouse)
How to break traumatic news to someone, if you're forced to be the one to deliver it.
People who have had a friend tell them bad news, usually try and relate as a form of support. I always do this and never saw anything wrong. After having it done to me recently, I understand the issue. If you do this, please just have the first thing you say, not be about you, that's all
I just realized that this is a situation I'd be completely unprepared to deal with. Is there a "proper" way to go about it?
Ask if they want to talk about it, or simply say "I'm sorry to hear that" then move on.
What’s a good way to respond to someone telling you sad news?
Sometimes I feel like I don’t know how to respond to things people tell me, whether it’s good news, bad news, etc. I’ve noticed I have a very limited number of phrases I go to and I feel like I’m being disingenuous. I started paying attention recently to how I bad about responding to sad news. Like I don’t think I understand the phrase “I’m sorry”. I know that in a literal sense, it means “I’m filled with sorrow/I’m regretful”, so saying it tells the person you can empathize with them. Somehow it still feels weird to me because it seems like your centering the conversation around yourself when you say “I’m sorry” in response to their sad news. I know people usually say “I’m sorry to hear that” but I don’t understand why. I was listening to someone respond to another person telling them sad news, and they seemed to have the “correct and good” responses. I stayed silent in the interaction because after a short period I ran out of things to say in response. Like I don’t think I fully understand how to respond to sad news. It always feels forced and awkward when I do, even if I feel their turmoil internally. It’s like as soon as I try to express this, I lose my words and can’t find an appropriate way to respond. Any advice?
EDIT: Related tip: if you have a close friend going through a divorce, it may be helpful to (tactfully and discretely) tell mutual friends or coworkers so people can get their dramatic reactions out of the way without it having to land on the person in question. How do you react after receiving bad news? Like someone passing away or being rejected in a position that you really wished for?
By thanking for informing. Regardless.

 
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