ShibbOleth, I’m glad you want to reach out to your friends. That is the most important thing. I’ve had miscarriages and had a toddler die because of leukemia so I think I can safely advise, that it’s not what you say, but that you say or do something rather than nothing because whats happened makes you uncomfortable. While it is possible to inadvertantly say something wrong. It’s amazing the number of ‘friends’ who are scarce and say nothing at all when life dishes out disaster. I admire and applaud you for wanting to know what a compassionate approach would be.
I recommend two books, both of which you can probably obtain at the library or a used bookstore, I Never Know What To Say, by Nina Herrmann Donnelley and The Art of Condolence by Leonard M Zunin, M.D. and Hilary Stanton Zunin.
That said, as to incident 1, because the death of a parent is the most common form of bereavement in the United States and touches a universal chord extreme grief in an adult child is considered by some to be unnecessary, maybe even inappropriate, your friends grief process may be stifled. Rather asking your friend how the surviving parent is holding up, focus on your friend. You friends parents will have their own support network which in fact includes your friend.
For incident 2,
I suggest you send sympathy notes to both friends. Send your sympathy not to the person with whom you have the closest relationship. (Not the parent in incident one, for example, but to your friend.)
Write promptly, send your note soon. Email is ok, but a handwritten snail mail letter is better. Any stationary is fine, butwhites, grays, pastels are better than bold colors.
Although etiquitte books tend to suggest brevity I disagree, length is not a consideration, your note can be as short or long as it needs to be to convey your sympathies and support. One of the most comforting letters I received included a story retelling an incident with my younger son, that a friend knew I missed because I was playing with her older and my older son when my son did something cute. Years have passed and I still treasure that letter, and it was not a brief note.
Write what you feel. Use the words “died” or “dead” and not “lost”, “sleep”, or “passed on”. I can’t tell you how stomache churning it is to hear someone the mourn because I “lost” my children. On the matter of what NOT to say, I recommend being careful about advising or telling your bereaved friends what to do or how to feel. When someone would say, “Buck up”, “It’s God’s will”, or “At least he’s not suffering anymore” I wanted to slap them rather than thank them for their condolences. You’ll do fine just remember that your letter or note is one of empathy and compassion. Acknowledge the death, express your sympathy, note special qualities of the deceased and recount a memory if you knew them, note a special quality of your bereaved friend, offer your help if appropriate and then close with a thoughtful word or phrase. Like “Affectionate respects to you and yours.”
Hope something here helps you,
Abby