What Does Red-Letter Day Mean?
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The letter in this expression is not about letters that arrive in the mail. Rather, it is about text on a calendar.
The Catholic Church used red text to mark special holidays and festivals, such as saint's days, on its calendars. Because these holidays signified feasts and other fun events, people associated days with red writing on them as good, happy days.
Some sources claim that the origin goes back even further, to ancient Rome, perhaps as far back as 500 B.C.
In modern contexts, a red-letter day has come to mean any special occasion.
In this example, a woman is talking about her job to her friend.
Neha: I'm about to give up on my job and just quit. I'm making less than all my coworkers, yet I do more work!
Tyrese: Really? You should ask for a raise.
Neha: I know, but my boss never grants raises. It would have to be a truly red-letter day for that to happen.
In this example, two office workers are discussing some good surprises.
Barry: This is such a great day! First, Donna brought in all those doughnuts just to be nice, and then Gary brought in cake for lunch because it's his birthday. Now the Internet has stopped working, so we all get a break for a few hours!
Rachel: Yeah, I love red-letter days like today! They don't come that often.
This example is about how to make sure to have enough money to last through retirement. The excerpt uses red-letter day to refer to the first day of someone's retirement, since that is something many people really look forward to for their whole lives.
This excerpt is from an editorial that is about how great it will be when American women have achieved getting elected to the highest job in the country: president.
The term red-letter days are days that are special in a good way.