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"is there a memory of them you'd like to share?"

Nothing, I say nothing

“yeah!? Ya know I’ve been thinking about them, too?”

If you are uncomfortable and don’t want to go too deep, maybe try to ask questions with concrete answers like, “When did they die?”, or “What made you think of them”? If you don’t mind and want to delve deeper, ask how they died, how they are dealing with it, etc.

Im not sure of the right things to say but this is what I’ve done for a friend in the past who’s mother passed away somewhat recently. I started by saying something along the lines of “I know you’re sad and I just want to say I’m sorry for your loss, I’m also proud of you for being strong this long.” Then I asked her things like “What was she like?” “What was your favorite thing about her?” “What do you miss about her?” “What’s your favorite memory of her?” All while emphasizing it’s normal to be sad. It’s okay to grieve over a lost loved one. It’s not going to be something that just goes away. You’ll always miss them, but try to think of all the good and even the bad times you had together. & when she answered those questions I asked her I told her that her mother seemed like a truly great woman, but the beautiful thing is that you’re just like her and your carry those parts of her on with you.

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"he/ she clearly was a wonderful father/ mother / friend/ etc and I'm sure they'd be proud of how much of an influence they had on you"

It truly depends on context. They might not even be looking for condolences. If it was a traumatic event and they're still shaken then I might simply say I'm sorry, and do you want to talk about it?

I agree. As adults, most of us have lost people we care about. Unless it was recent, I don't expect anybody to assume I'm still grieving over a loss. If there's something about that person I want somebody else to know, I'll come out and tell them.

I lost my grandmother, who I loved dearly, two months ago. I don't expect anybody to feign sympathy or ask questions about her. She was 90, it didn't exactly come out of nowhere.

As someone who’s lost people long ago, simply “I’m sorry to hear that” or “my condolences “ is enough. Grief is complicated. If they want to tell you more, they will.

You say politely, I’m sorry for your loss, then they say something. Most of the time, they say something like, thank you, it was a long time ago and the conversation goes on. Sometimes they want to talk.

You let their reaction guide the conversation.

1. A short acknowledgement - e.g. 'I'm really sorry to hear that.'
2. Pause - offer a short break for them to open up (you never know how important this could be to someone)
3. Move on with the conversation.

That’s actually really nice.

Right. We don't know anything about the context.

Someone saying something like "Back when Mom was alive, we'd have Christmas dinner at my parents' house." That requires no response.

On the other hand, someone saying "I still can't believe Mom has been gone for thirty years. Seems like only yesterday." might be looking for a little sympathy.

What's the LPT from this????

Nothing. Just listen.

Oh God do I hate it when someone tries to fix it by making suggestions.

Exactly. People say some really cruel stuff, inadvertently, trying to fix it.

my kid’s preschool teacher lost her toddler last year, i has absolutely no idea what to say aside from “i’m so sorry.” advice i received after the fact was to ask what their baby’s name is, not what it was, then repeat the baby’s name. it’s a gentle reminder that their baby existed, and they’re remembered by those who never got to meet them.

not all who die, die old.

This is a perfect answer. If it’s someone you feel an emotional connection to and want to encourage them to open up, adding a remark such as “I can’t imagine how difficult that must have been” or similar. This I learned from a “death and dying” class.

In my experiences, a hand on a shoulder and a simple nod of understanding have been a good way to get it across that you feel for them, and are there for them. From there I’ll say, “if you wanna talk about it, I’m here. If not, I’ll chance the subject.”

https://www.youtube.com/watch?v=CHSIYGP0l_w&ab_channel=TheGuysTravel

My sibling was killed years ago when we were teenagers. All I need to hear (if ANYTHING) is “I’m sorry to hear that” or something similar.

I think you should ask this question in r/relationshipadvice not here

What were they like?

I reduce the sincerity of my empathy 3% for every year that has elapsed

It depends. If it was about someone that you also knew well, you could say something sympathetic like "Such a lovable man" or "Such an admirable lady".

I have people who insult me about my dead dad from time to time just go for it.

I usually share my condolences and ask if they'd like to share a good memory of their loved one. I believe allowing them to remember the good times brings them closer to their loved one's memory.

' tell me about them'. ' will that bring them back? ' ' for a little while, it will'

And please don't say something similar to "oh I know how you feel because I ... "

Don't divert the discussion to yourself.

We miss them too

Offer condolences but then say “what was their name?”, sometimes the person will break into a funny or heartwarming story but mostly it just calls out to the universe that they’re still here.

I heard a while ago that we die twice; once physically and once the last time we are remembered. Give them a chance to remember again.

I don’t like making others uncomfortable so when I talk about something my son did (usually makes me smile now) I do it as though I still have him. Because being able to talk about him keeps him with me.

“I’m sorry. I’d love to listen if you want to talk more about it.”