The short answer:

It’s appropriately informal and honest.

The long answer:

Back in the day, I never thought about how to begin and end letters. It was a simple “dear” to begin and a “sincerely” to end. If I was feeling spunky, I’d write “sincerely yours.” I know—I’m a wildcat.

But then once when I was writing a letter, I wrote down that “dear,” and it felt weird. It’s like when you read a really common word over and over, and then suddenly you’re not sure if that’s really how you spell “the.” (The. The. The. The. The?) I started thinking, why do we always start letters with “dear”? I never tell anyone that they’re dear to me in person. In fact, most people I write letters to aren’t dear to me at all. It didn’t make any sense.

So I decided to write “dearest” instead, even though this person was by no means my “dearest” at all. The two words are practically the same anyway. It was supposed to contain a whiff of whimsy, an iota of irony, or perhaps it would just call attention to something peculiar that we always take for granted. I thought it was pretty clever.

Instead, I’m pretty sure it was just freaky. I had not considered that it is difficult to convey such subtleties as whiffs and iotas with chicken scratch.

Hence I decided that it is not a good idea to mess around with salutations. Just write “dear” and be done with it. But I needed to release my pent up caprice somewhere. Luckily, there has always been much more freedom in the valediction. Though “sincerely” is probably the most common, there are a number of other socially acceptable options, and so I set about to pick an appropriate one for use in my casual correspondences.

I rejected “sincerely” because I thought it sounded too formal. If you tell someone that you’re being sincere, then it means you aren’t kidding around. This did not seem to be appropriate at the end of an email filled with questionable humor, bad puns, and perhaps a fart joke.

Some people like “truly yours” or “yours truly,” but I didn’t feel good about either of them. You don’t own me. Am I truly yours? What does that even mean? Perhaps “falsely yours” or “truly mine” would be more accurate.

I felt that “best” was not the best choice either. Sure, it sounds nice that you are wishing someone the best, but it’s a little empty. Of course you want the best thing to happen; that’s why it’s the best. Frankly, I could use something more specific.

Some people I know use “regards.” I felt that this is also a bit empty. If you ask me to send your regards to someone, I’m not sure what that means. Apparently, you are regarding them. I’m sure that helps them out a lot.

So I settled on “cheers” for a few reasons. First, it sounds very familiar and informal. Second, it’s a nice, honest thing to wish upon someone, that they be cheerful. Third, it’s a bit of a Britishism, making it stand out and giving it a sort of quaint charm. Fourth, it’s an anagram of “Escher,” who’s one of my favorite artists.

Hey, it’s more exciting than “bets” or “graders.”

Cheers,
-qm