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on 2006-06-05 21:47 (UTC)i used to feel very similar to you about "i'm sorry", but i can handle it much better now. because most of the time what it means is "i am sorry that this happened to you", which is akin to saying "sorry for your loss" to a grieving person. and that's all a sympathetic stranger can say as the first thing without feeling foolish or overstepping bounds. i've come to actually prefer it from strangers, and i simply reply with "thank you". i don't feel that it is turning the conversation away from me at all; it just feels like an acknowledgment of my pain. it does, however, not per se encourage me to open up more about it; for that i need some additional words.
on the giving end, i've turned that insight into being more explicit about what i am actually sorry for, so it can't easily be mistaken for a request to be absolved from guilt, or given aid with my own discomfort. i'll say "i am so sorry this happened to you. do you want to talk about it? do you need anything? can i do something to help?". not always all those at once, but they tend to be the most common options. if i know a person well i might not speak at all, but if i know a person well i don't need general guidelines for what to say anyway. if i don't know a person i feel moved to say something because i want the person to feel safe to talk (or not talk) as zie needs.
on the other hand, "how does it feel..." rubs me completely the wrong way, like a reporter who sticks a mic in front of a father who has just lost his son. that is one of those pseudo-therapist comments that instantly make me clam up. it might fit later in the conversation, but i'd never ever say this as the first thing, after somebody has blurted out "my boss is sexually harassing me", for example.
i think i basically avoid the whole "shouldn't happen" in all its incarnations, because it's just too much about fantasy than about the horrid thing that did, in fact, happen.
"i feel privileged that you trusted me with this story" is for the end of it, not the start. that one definitely feels like it could easily pull things into "hey, look at me!" territory, and i am really careful with saying it, even though i do often feel it.
"wow" is ok as the first thing out of my mouth, and it might even happen involuntarily. but standing on its own it feels insufficient; it's too open to interpretation. i like explicitness in general. "tell me more if you're willing" is great. depending on the circumstances i might admit that i am uncomfortable, and that i might not be the best person to talk to, and offer to help find somebody else.
i think your comments about approaching it on a very personal level, and gently probing are really important. emphasis on "gently". this should happen at the speed of the person who's hurting. one size does not fit all. and yes, it makes a difference to my approach whether i think we're engaged in a conversation, a debate, whether i am listening to a story, or whether i am in an advisory position. online discussion feels generally like a conversation or debate (and i avoid the latter), unless the speaker defines it otherwise at the start. this is an area in which i am learning to step much more carefully because oh man, livejournal is so much less automatically about conversation than usenet is.