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I think it's conventional to say "I'm sorry" when offering condolence -- for example, "I'm sorry to hear your mum died", or, "I was sorry to hear your mum died".

Although it may be conventional I have three difficulties with it:

  • I don't know how to reply if or when it's said to me
  • I figure it may trigger a person's grief anew, and is therefore hurtful to them -- for example there they are, conversing with me, and suddenly here I am reminding them of their recent bereavement
  • It's superficially or literally about me and my emotion -- "I am sorry" -- seems quite selfish, when it is they who are grieving ... as if I am inviting them to reassure me

My questions:

  • Should I get over my hesitation and just say it, because it is conventional, and I should trust that it's therefore correct?
  • Is there an alternate/better phrase to use, perhaps a more tactful way to open the subject?
  • What is the subject really? It seems to be, "I don't know what else to say but fear it may be rude to say nothing."
  • Do you prefer "I am sorry to etc.", or "I was sorry"?

The context is:

  • English-language, UK or Canada if that matters (or the equivalent in French in France, « désolé »)
  • Spoken or written, to a friend or extended family
  • Perhaps but not necessarily in person, and not necessarily at the funeral -- when I'm meeting the bereaved socially for the first time since their death
  • Possibly too as a reply to someone telling me about their loss (i.e. "My mum died" -- "I'm so sorry to hear that"), where I'm worried that the subtext might seem to be "That's bad news, I wish you hadn't told me" which wouldn't be the right message.
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"I'm sorry for your loss" is definitely appropriate when offering condolences:

While this phrase has become a cliché, it is also a simple and succinct way of communicating your empathy. If you are at a loss for words, telling a person “I’m sorry for your loss” can let the person know that you care. 1

It is indeed a standard fall back for when you don't really know what to say, but want to let the person know that you care about them. Also, the sorry in this case acknowledges their grieving, and extends sympathy:

Feeling distress, especially through sympathy with someone else's misfortune. 2

The chances will be very small you'll be seen as the one wanting reassurance. Instead, you're extending sympathy for their misfortune, letting the person know you care about them.

I think you need to work on your timing though. You say: 'there they are, conversing with me, and suddenly here I am reminding them of their recent bereavement'. Condolences and sympathies are usually offered at set times:

  • During a visitation. This is after death but before burial.
  • While greeting the mourners briefly before a funeral or memorial service.
  • At a gathering following the burial or memorial service. 3

Since you're talking about friends and extended family, if you can't make any of these/aren't invited to any of these, a written condolence would be preferable. In The Netherlands, it is proper to go buy and send a card with your support the same day/day after the news of the death reaches you.

When you haven't seen someone for a while, and want to express your condolences upon meeting them for the first time since their loved one died, you do so upon their arrival. Over here, that's appropriate for e.g. coworkers that return to work after bereavement leave. Timing is always still a bit awkward, but usually you wait until someone has walked into the door, said good morning and has taken off their coat. The same could be applied to friends visiting you. Do NOT randomly put your condolences into the middle of a casual conversation. It ruins their value and makes it much harder to take them seriously for the bereaved. Of course, if the bereaved brings it up themselves, it's appropriate to acknowledge their loss and grief.

As for the alternatives to saying 'I'm sorry for your loss', there are plenty out there on the internet.. Find one that works better for you personally, and you can use it in the same way most people use 'I'm sorry for your loss'. You can combine another sentence with "I'm sorry for your loss", or keep a small mental list and pick one or two that seem most appropriate for the situation.

Your example of "I'm sorry to hear that" may miss the part about 'your loss', it misses acknowledging the other person. To be safe, I personally stick with condolences that explicitly acknowledge the other person and their bereavement. "I'm sorry to hear about your loss" feels like a better reply than "I'm sorry to hear that", even though most people will interpret it just the same.

When someone offers their condolences to you, you accept them gracefully and genuinely. 4 A simple 'Thank you' works. If you're e.g. glad to be back at work and don't want to talk about it much, usually 'I'm glad to be back' is enough of a hint. Since you're the person grieving, you can basically do everything from telling people how much you still miss the deceased to sharing fond memories. Don't worry too much about it, things may get a little awkward but this is one of the few times in life where that shouldn't matter much.

And sadly, as always... practice makes things easier. The feelings never get easier, but after having given and received condolences a few times, the rituals do.

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    I would add that if the bereaved is a close friend/relative/... adding something like “please let me know if there is anything I can do” or “ I’m here if you want to talk” can help make it about them. Of course, only if you feel comfortable about this and will actually follow through when they take you up on your offer. – AsheraH May 9 at 15:01
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Dealing with grief is, quite simply, challenging. We all deal with grief differently and different cultures express grief differently.

I'm not familiar with grief customs outside the midwestern US, so please forgive my US-centric answer.

First of all, your response to a person's loss isn't for you - it's for them. Typically I want to convey a message of sharing their grief and supporting them in their grief. To respond to your first question - what's correct is saying what will get your message across. If it was a person they hated (abusive parent/spouse, for example), "I'm sorry" may not be what they want to year. One thing I've heard people say is, "Wow... were you close?" That clues you in to what to say next.

WRT question #2: who is opening the subject? If it's you.. why do you want to open it? Do you want to walk through their grief with them? Do you want to do the "right" thing? What is your motivation? Sometimes I'll respond with "Please, tell me about them... I did not know him/her". Their response can help guide you through your response as well.

Very few people know the right thing say to the grieving, due to my first point. It's been my experience that listening is quite often the right thing to say. Sometimes the grieving want someone to just listen. Sometimes the grieving want someone to do something normal with them just for a little distraction. Sometimes the grieving just want to get stinking drunk. The important thing, again, is to listen and respond to what they say.

WRT question 4: this is a question of timing. If it's recent, then "I am sorry" is more appropriate. If you heard second-hand of the person's death and were not there to talk with the bereaved, then "I was sorry to hear [X] died" may be more appropriate. As the interval increases, the change in tense can happen. When not sure, put it in the present tense - "I am sorry".

In the end, as someone who is attending seminary and has taken training on this subject, there's no easy right way to deal with someone's grief. It's hard, and requires attention on your part. But if you do pay attention, you can be a valuable part of their grieving process and will have a very good idea what to say/do. And as you do it more, you'll get more in tune with how to support people at a very hard time in their lives.

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