Because That Mr. Dimmick Who Thinks He Knows So Much was recently bereaved, Etiquetteer thinks this is a Perfectly Proper time to review the basics of condolence correspondence.
GUIDELINES FOR SENDING CONDOLENCES
Write as quickly as you can. Condolences make a positive difference whenever they are received, but especially in the days immediately after a death and/or a funeral. That Mr. Dimmick received an email message from a Dear Friend that began "I know a handwritten note is more appropriate in moments such as this, but I find that speed is more important than propriety." Both speed and propriety are important, but while the speed of the Internet is taken for granted today, the appearance of an envelope in the letterbox remains double touching when one is bereaved. When in doubt, there's no reason not to send both an email and a handwritten card or letter.
But write anyway, whenever you do. Sometimes it feels embarrassing when someone is bereaved and you haven't communicated your condolences at all, for whatever reason: couldn't find the right card, couldn't think of what to say, heard the news months later, personal aversion to acknowledging Death, just plain forgot. Months can go by. Taking the trouble to communicate condolences, whenever they're communicated, no matter how long after the funeral, makes a positive difference. Cover any embarrassment you might feel with the phrase "You have been on my mind since the death of [Insert Name of Deceased Here]" or something similar.
There's a lot of Perfectly Proper stationery out there, so don't use that as an excuse. For those uncomfortable using their own letterhead, there are many Appropriate Cards on the market from which to choose, some of which appear in the image above. Mostly in neutral shades and/or patterns, they all incorporate sympathetic language, either secular or religion-specific. Images from nature are also very popular. When shopping, if you find one you like, buy a dozen or more to have on hand when needed.
Non-condolence-specific notecards may also be used. Certainly the most original and appropriate choice of those pictured above was that of the Black Cross by Russian artist Kasimir Malevich. Still, as they say in the fashion world, "You can never go wrong with a classic." Plain black-bordered notecards in white or ecru, like these from Crane's, are always Correct.
By the way, using one's own letterhead is Perfectly Proper for all correspondence, including condolences. Some sticklers would even say it is More Perfectly Proper than a condolence card, while others Etiquetteer would call Small-Minded don't consider a condolence a condolence unless it's written on a condolence card. Etiquetteer considers anyone who would complain about the way in which people offer them sympathy unworthy of it.
Use your full name and address. It's easy, when writing to people one knows, to save a bit of time or trouble by omitting a return address from a sympathy card. Don't give into that Slothful Temptation. The return address you write (or stick) onto a sympathy card is one less address the bereaved will have to spend time finding. Similarly, you may think yourself the only Beowulf in the life of the bereaved, and might be surprised to learn about them wondering if your condolence came from Beowulf "Bay" Brummell in Arizona or Beowulf "Wulfy" Brummelli in Accounting. Help out the bereaved by including this Useful Information somewhere, even when you're sure they already know it. It will make a difficult task easier.
Originality is unnecessary. Many correspondents will delay writing a condolence because they want to think of something original to say, either about the deceased or about the situation. But if those words don't come, write and send them later when they do pop into your head. There is no shame, and actually quite a lot of good, in responding quickly with the same thoughts that everyone else is having: that you care about the bereaved, that you care about the deceased, and that you want to help.
Be understanding if you don't hear back for awhile. No matter how you send your condolences, the bereaved have a lot going on and may not reply very quickly. If you sent your condolence electronically, it never hurts to send another email along the lines of "Thinking of You" after a week or so.
GUIDELINES FOR REPLYING TO CONDOLENCES
Find the right stationery, but don't let the search slow you down. The stores don't always have the Right Thing when needed, and it isn't always possible to wait to reply to condolences for an order to be delivered from Who Knows Where. That Mr. Dimmick was fortunate to discover some Perfectly Proper black-bordered cream notepaper on short notice.
In a very few instances, since Excessive Embellishment is the antithesis of mourning, That Mr. Dimmick used notecards engraved with a peacock feather. While the peacock symbolizes immortality and eternal life in some religious traditions, Etiquetteer looks on this level of embellishment as the Thin End of the Wedge. That Mr. Dimmick also found, in the dark recesses of his stationery wardrobe, a box of notecards emblazoned with dancing skeletons. Needless to say, that was considered Not at All Perfectly Proper, and back they went. Gallows Humor has its place, but this is not it. Most decidedly not!
Reply to condolences in the manner in which they were received. Handwritten condolences are replied to in handwriting.* Email condolences are replied to by email. Condolences received via social media are acknowledged via social media. In the last case, it's not necessary to respond to individual comments under a status update (but you may, if you wish). A single comment thanking all for their condolences will be seen by all, and that comment may be added again after subsequent responses.
Be brief. Death brings many stresses, and many things to be attended to, which means that there may not be extended time to spend on correspondence. It's not necessary to write more than "Dear [Insert Name Here], Thank you for your kindness at this difficult time. Yours gratefully, [Insert Your Name Here]." A reply can be heartfelt without being long-winded.
Anyone in the family may reply. Death brings up a lot of emotions, and not everyone is ready to respond to a pile of condolences, even those it is "easier" to respond to electronically. One or more Capable Family Members may be detailed to reply "on behalf of all our family" or "on behalf of [Insert Name of Prostrated Mourner Here]" without any lapse of Perfect Propriety. It would be Bad Form for recipients to protest "But I was hoping to hear from [Insert Name of Prostrated Mourner Here]."
A reply makes a difference. Aside from learning that their condolence was received, your reply to a condolence reassures correspondents of your current state.
While of course Etiquetteer hopes you won't have to use these guidelines any time soon, it never hurts to Be Prepared.
* Sticklers will here try to ensnare Etiquetteer and other writers into a debate on the merits and demerits of handwriting vs. typewriting or computer printing. Etiquetteer admits to finding this debate tedious in the extreme. If someone writes by hand and you prefer to type/print a response for whatever reason (the one that seems given most often is illegibility), then go right ahead and do so. The reverse is also true.