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It’s sometimes easy for meaning to get lost in written communication, so it’s necessary to make faces with text. Emoticons and their derivatives have helped convey meaning since the beginning of digital communication—a simple smiley face (composed of a colon and parenthesis) can soften a hard confrontation or add humor to an otherwise somber exchange.

There are a few different ways you can add emoticons, emojis, and Lenny faces to your writing, and it’s important to know the most appropriate circumstances to use each one. Keep reading to learn more about these symbols and how to use them. 

How to make faces with text

  1. Open a new word processing document, email, text message, or instant message.
Screenshot of empty message box in Slack.

Screenshot of new message open in Slack

  1. Type a combination of symbols, numbers, and letters to express the face you want. Some applications will automatically turn emoticons into emojis.
Screenshots of sample text with faces in Slack message box.

Screenshot of Slack message with an emoticon that is automatically replaced with an emoji

  1. Alternatively, you can copy and paste from a database of emoticons, emojis, and Lenny faces. Find a list of popular databases below.
Screenshot of Lenny face example in Slack message box.

Screenshot of Slack message with pasted Lenny face example

Examples of emoticons

The infographic below illustrates some of the most common emoticons and the keyboard characters that make them:

Infographic of emoticon examples: :), ;), :D, :(, :'(, >:(.

Emoticons vs. emojis

Although they are often used interchangeably, there is a significant distinction between emoticons and emojis. First and foremost, emoticons are more rudimentary and were commonly used in the early days of the internet. They use simple key combinations, like a colon and a parenthesis. They are universally recognized across languages, operating systems, and applications.

Emojis, on the other hand, are a new generation of emoticons that use illustrations instead of plain text. They were first developed in 1999 by a Japanese artist, but they didn’t gain widespread popularity until they were accepted by the Unicode Consortium in 2010. New emojis have been introduced since the original set, and emoticons are sometimes used in situations where a suitable emoji doesn’t exist. For example, the :’) emoticon was often used before the ? emoji was introduced. 

Variations of the original drawings currently exist in most operating systems, including Android, iOS, macOS, and Windows. Some applications, like Gmail and Twitter, use custom emoji sets as well. As noted above, some of these platforms automatically replace a typed emoticon with its emoji equivalent. 

Usually, the situations where it’s appropriate to use an emoticon are also appropriate for an emoji. These include informal modes of communication like instant messages, text messages, and social media posts. On the other hand, formal communication mediums like email, websites, and word processing documents are usually inappropriate for emoticons and emojis. This is relative, however, as emails between peers and personal blogs often contain emojis and/or emoticons.

What are Lenny faces?

Lenny faces are Unicode-based images that function somewhere between emoticons and emojis. They aren’t as graphically advanced as emojis, but they more closely resemble human faces and expressions than emoticons. 

Popular Lenny faces include:

( ͡° ͜ʖ ͡°)

¯_(ツ)_/¯

ಠ_ಠ

Lenny faces cannot be typed with keyboard characters as easily as emoticons, but they are not directly integrated with operating systems and applications like emojis. Instead, Lenny faces involve complex keyboard combinations that aren’t supported across all devices. Smartphones and Mac computers, for example, aren’t capable of creating Lenny faces. In most cases, it’s easier to copy and paste a desired Lenny face from a database. Examples of popular databases include:

History of Lenny faces

The original Lenny face— ( ͡° ͜ʖ ͡°) —first appeared on the Finnish image board Ylilauta in 2012. It immediately gained popularity on other message boards like 4chan and Reddit. Several users were banned for using variations of the Lenny face for spam and harassment.

In less hostile parts of the internet, the Lenny face quickly became a meme. The day after the original Lenny face was posted, one YouTuber uploaded a satire video of Lenny faces animated to the Fresh Prince of Bel-Air theme song. It went viral, amassing more than 865,000 views, 3,000 comments, and 13,000 likes.

The origin of the name of these faces is somewhat of a legend. According to one Reddit user, the name was born out of satire:

Although it is unclear where the name “Lenny face” came from, they are certainly a recognizable part of internet culture.

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