Reaching out vs. Respecting boundaries

Earlier today, I was talking with a friend about our 4ths and she mentioned her significant other's parents had visited and how the dad is wont to talk incessantly, not about anything necessarily related to the current conversation, and he'll follow you around and keep talking to (or rather, at) you even as you're shutting the door to the bathroom. He's always been like this, apparently. I really wanted to say, "My mom does that, too," but then somehow we changed topics and the moment passed.

I remember once overhearing a former boss say to somebody else on the phone about how her husband was depressed, and she was trying to explain it to whoever was on the other end of the line, but she didn't seem to be having any luck. I wanted to say something, to tell her that it's something I've also struggled with, but a.) I had overheard it, and b.) I didn't know if she wanted me to know.

Sometimes opportunities present themselves and usually I do not take them and then kick myself afterwards. What if I told them something they didn't want to hear? Like, hey, your father-in-law's odd behavior sounds like my mom's and she has a mental illness so maybe he does too! I mean, I guess it is better that he get treatment if that is the case, but then again it may just be some quirk of behaviour that has nothing to do with mental illness. And then there is always that question of how much is too much information to share at work.

Illness and abnormalities make people really uncomfortable. Just ask anybody who's an amputee or visibly a burn victim. Yeah, there's all this ra-ra-bust-the-stigma and it's cool to smash taboo and whatnot. But just like in cognitive behavioural therapy (or whatever that method is for helping people with phobias through gradually increasing exposure), I think dealing with stigmas is one of those things that is a nudge-over-the-edge type thing rather than a sink-or-swim type thing. (Such an articulate sentence, I know.) Sometimes getting to know someone of that "other" group or some other type of interaction/experience speeds this up a lot, but rarely are such planned occurrences effective. All those exercises about stereotypes in school were just awkward and sometimes self-defeating.

Sometimes too much too fast just pushes people in the opposite direction. Not trying to knock Augusten Burroughs, and admittedly I haven't finished the book b/c I can't remember where I put it, but Running with Scissors just seemed like another memoir in the veins of I-had-a-fucked-up-and/or-bizarre-childhood. Augusten Burroughs is "that guy" at the party, much like Dave Pelzer or [insert name of someone else who wrote a memoir about traumatic experiences here]. The further something is away from our own experiences, the harder it is for us to identify with them, to truly empathize, and to understand. We don't even try; we just pity them. For me, the first book that really spoke to my experience was Phyllis Reynolds Naylor's The Keeper. I read it and kept thinking, "Yes, I know that feeling exactly!"

Anyhow, getting back to my original quandary....

When do you reach out to someone, take that step in their direction? And when do you respect whatever boundaries they have set about what they're willing to share with you?