I run into a lot of "Things You Should Never Say to a [fill in the blank]" articles, and I feel like they are dreadfully unhelpful to prospective well-wishers. I've been on the giving and receiving end of comments that really should never have been said, so I have come up with a couple of rules of thumb for the givers (and receivers) of comments in difficult contexts.
To Comment Makers:
1) Sometimes the best thing to say is nothing. If you don't know what to say... maybe you should just say that. Telling someone you don't know what to say is a heck of a lot better than making a comment that's going to be ringing in their ears for reasons you might not understand.
2) When making a comment to a new mother, prospective mother, or the mother of a sick or dying or special-needs child, you almost can't win. You don't know where she is emotionally or on the sleep-deprivation scale when you are talking to her, but you can pretty much guess, so anything other than "You're beautiful," "You're doing a great job" or sincere offerings to help is almost certainly going to be taken the wrong way. Just listen. Give advice ONLY ONLY ONLY if she asks for it, and even then, tread carefully, my friend. There be dangerous waters.
3) When talking to a grieving person, one thing he sometimes longs for is just to talk about his loved one. Yeah, everyone else in the room is squirming because they wish for the love of God that we could all move on and forget that bad thing ever happened, but if he wants to remember that person, sometimes that in itself is therapeutic. Let him talk and remember. It can make him feel better, even if there are a few tears.
4) Please don't compare yourself to your friend or guess what you would do in his/her situation. You really have no idea if you've never been there before what you would do, and even if you've had a similar experience, you are a different person, so for goodness' sake, don't guess or compare your experience. Your friend's grief or challenge is not a good moment for your own self-evaluation.
To Comment Receivers:
1) Put yourself in your friend's shoes for half a second and try to see things from his/her perspective. She is probably clueless, but she means well. So he told you that your loved one is in a better place, or he mentioned that your new baby looks a little like a monkey. Maybe she had a harrowing birth experience and she just wishes she had been warned and she thinks she's saving you somehow by scaring the bejesus out of you. Be gracious. Your friend is a well-meaning idiot, but unless she's being genuinely and intentionally insulting, it's a good idea to chalk it up to bad communication and move on, especially if this is a friend you like and want to keep.
2) On that note, do you know you're allowed to tell your friends that they've hurt your feelings or insulted you? Or you can even verbally disagree with them so that they can understand in some way that maybe that wasn't the most sensitive comment they could have possibly made. I think a lot of people take comments that have hurt them silently, then let them sit on their hearts and maybe even take it to social media to complain there, but never saying a word directly to the person who (accidentally) hurt them. Not good for relationship building.
3) If a stranger has insulted you, it's open season. Vent to your friends, add it to your "Book of Bizarre Exchanges with Strangers," put it on Twitter, or have a good laugh about it. That person's opinion by all standards does not matter. These are the same people who write comments on YouTube. Remember the judgments you make about others in your own heart that you happen to have the good sense not to say out loud and move on with your life. Everyone is entitled to their own opinions, even if their opinions are hurtful or ignorant, and be thankful you live in a country where we can freely speak our sometimes empty minds.
I have found that everyone is very different, and what comforts one person might offend another. Try to remember your empathy lessons from kindergarten and remember - a plate of cookies never hurt anyone's feelings.
Unless they are on a Paleo diet and you were just too insensitive to remember that about them.