At another vort last night (B"H for simchos) of a friend and relative's younger sibling, we were having the conversation of how, in essence, common sense ain't so common.
Instead of saying Mazel Tov when hearing that the younger sibling got engaged, the general comment was, "How are you?" People assuming that I'm not okay because my younger sibling is engaged is annoying. Maybe I am and maybe I'm not, but why do you have to jump to that conclusion and/or rub it in? (I'm speaking from my own experience too.)
I thing it's really best to take cues from the person herself/himself. If I don't talk about it, you don't talk about it. There are more tactful subtle ways to go about that conversation as well. You can ask "what's up" or "how are things" and if the person wants to share what they're thinking or feeling about the younger sibling being engaged, s/he will. It's about respecting privacy and boundaries, not prying, not being annoying, not rubbing it in her/his face that s/he might have a reason to be sad.
So yes, it's a delicate balance, because some people expect you to ask. If you're not sure though, play it safe and be neutral. Never say, "You know you can talk to me." For me, what was most amusing and slightly frustrating (and perhaps a tribute to how I form relationships) was that when my younger brother got engaged/married many many people said, "But I can ask how you're doing..."
We're all human and we'll make mistakes, but it's helpful to be cautious and try not to hurt people unintentionally. On the receiving end, like someone reminded me recently, this is one of those things that is part of the nisayon of being single. There are so many added things that are difficult that are indirect outgrowths of not being married. This is one of them.
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