From the wonderful, beautifully researched, and soon-to-be-published book Because Internet: Understanding the New Rules of Language by Gretchen McCulloch.

The story of the acronym “lol” for “laughing out loud” is a great example of emotions leaping out of the internet and into the physical world. The most commonly accepted account of the creation of “lol” comes from a man in Calgary, Alberta, Canada, named Wayne Pearson, who recalls coining it in a chatroom in the 1980s: A friend of mine who went by Sprout (and I believe he still does) had said something so funny in the teleconference room that I found myself truly laughing out loud, echoing off the walls of my kitchen. That’s when “LOL” was first used.

We of course had ways of portraying amusement in chatrooms before that (>grin< >laugh< *smile*) and the gamut of smiley faces, but I felt that none of them really got across the fact that the other person just made you feel foolish by laughing out loud in a room all by yourself (or worse, with other family members in another room, thinking you quite odd!) The exact time and date when “lol” was created may be forever lost to cyberspace, but Pearson’s account does fit the facts we can verify.

The first known citation for LOL appears in a list of already common internet acronyms in an online newsletter called FidoNews from May 1989, as spotted by the linguist Ben Zimmer.

Regardless, Pearson’s story evokes the era of Old Internet People: an internet friend, a long-standing pseudonym, laughter at the computer, the bafflement of non-techy family members. Once the next wave of internet users arrived, people would become a lot less surprised that friends and funny stuff happened online.