By Will Schwalbe — Some of the most polite things people say can take on a totally different character when you write them in an email or in an IM or text message. Here are some examples.

1. Please
We are taught from an early age to say “please” when we ask for things. “Can I have some milk” doesn’t, in most houses, get milk to the requester. It has to be, “Please, can I have some milk.” (In the home of an English teacher, it would need to be, “Please, may I have some milk,” but that’s another matter).

So we are conditioned to believe that “please” is a polite word. And it can be, when it’s said politely. But it’s also often used in a preemptory, scolding, or sarcastic tone. “Please remember” usually has the implication of, “You’ve been told this before. Why can’t you remember? Is it so hard?” The same goes for “Please make sure to….” or “Please don’t forget…” or, basically, the word “please” with any command other than something obviously and overwhelmingly positive like “be my guest” or “help yourself” or “stay as long as you like.”

Curiously, in the very informal research my co-author David Shipley and I conducted, we found that the abbreviation “pls” doesn’t carry this scolding tone. But, as with all abbreviations, it’s clearly more appropriate for casual communication.

2. Okay and fine
These usually sound upbeat in speech but deflating in print. We live in a culture of hyperbole, and both words have suffered from it. In email, “great” equals “fine” and “good” equals “okay.” So it’s a good idea to make the substitution if you don’t want to disappoint. This is especially true when the words appear alone. If you write someone a long and detailed proposal and get back one word, and that word is “fine” or “okay,” it appears to be anything but. And who can forget the immortal phrase Fine, ferget it,” from the Travolta/Winger classic Urban Cowboy? The exasperated way it was said is exactly how it looks on a screen.

3. Thank you
The problem with “thank you” comes not when you use it after someone has done something for you, but when you use it before the person has done the thing. When you thank someone in advance, it’s really a command disguised as premature gratitude. So, “Thank you for bringing the donuts to the meeting” is nice if the meeting has occurred and the donuts were brought. But it’s galling to be thanked if the meeting is yet to take place, and really infuriating if the meeting has taken place and you were supposed to bring the donuts and forgot. Then it’s pure sarcasm.

Will Schwalbe is the co-author with David Shipley of Send: The Essential Guide to Email for Office and Home.