In an age when people can choose among text messages, email, Facebook and old-fashioned stamps and printed cards, the chance to use the wrong method when sending your very best is quite high.
What to do?
Well, the Associated Press went straight to an expert among experts: Judith Martin, author of the syndicated Miss Manners column, who offers guidance on dealing with the evolving etiquette of expressing sincere sentiments in an increasingly impersonal, digital world.
Her general advice is that formal events and intimate expressions require a handwritten note. But for more casual events and occasions, she gives people permission to send an email or text message greeting or even post to Facebook. Just keep it tasteful, OK?
Some of Martin's pro tips:
Getting married? Get ready to write.
"People do still have very formal weddings in which case the invitations and the communication and the expressions of gratitude ought to be in keeping with that style."
Never email the words, 'sorry your mom died.'
"You don't just dash off some casual thing on email. You sit down and write a real letter. Cards are a strange thing because they are in between. I've always been puzzled about why people spend hours selecting a card with a preprinted sentiment instead of just sitting down and writing a sentiment that they feel. It doesn't apply to Christmas cards or Valentine cards, where the picture is a great part of it. But to send, for instance, a sympathy card is the most impersonal way of reacting to something that is very deep and emotional."
Romeo didn't email love letters to Juliet. You shouldn't either.
"I can't imagine that you can print out your electronic love letters and tie a pink ribbon around them and press them to your heart. And yet I've been asked, 'Is it OK to propose marriage by texting?' That would not exactly touch my heart if I were the object of that proposal."
Disinvite the e-vite.
"If someone wants to see me, it seems to me that they can do it personally. If it's an informal party, send me an email. But I don't want to be part of a group that everyone can scrutinize who has been invited. What did this person say and what did this person say? I don't want to participate in a public group discussion about the party. Generally these people don't entertain in such large groups, except for weddings where they do send paper invitations, that they can't contact the individuals."
Don't send an e-card to Miss Manners.
"A lot of them annoy people because they take a long time to download and for those who are sentimental about cards, they can't keep them in the same way. Are you touched, amused, charmed if you get an e-card and you are trying to work and you download it and it has probably loud music that your co-workers are turning around to see what it is? It is an inconvenience and not very charming."
Are you really going to use Facebook to wish your mom happy birthday?
"Facebook has caused a lot of trouble because people don't realize that everybody sees it. Yes, you have privacy controls, but if one of your friends decides to send it on to someone else then you've lost that and it's there permanently. Now, I can't imagine getting in trouble by sending something nice to your mother but perhaps it contains a little zinger that you wouldn't want there permanently. And the amount of damage that people have done to themselves and others by posting things is enormous because these things are read by parents, perspective employers, by prospective lovers. People look and it's all out there. I don't think 'Happy Birthday Mother' does any harm, but you should watch what else you post."
Know where your friends are.
"You have to know someone's actual habits if you are going to reach that person. That's kind of a burden to have to know. This one doesn't answer the phone. This one doesn't check emails. I don't have a solution. I'm just saying that you should be familiar with the range of things that the people you want to reach or legitimately want to reach you use."