Over the past 30 years, emoticons have become a staple of digital communication. People rely on the smiley to add tone and feeling, which are often absent when communicating online. This is especially important in the case of text messaging and micro-blogging applications like Twitter where characters are limited. An emoticon can make all the difference between what might be perceived as a malicious jab vs. a good-natured joke.
The controversy surrounding WordPress’ built-in support for smilies has surfaced again in light of WordPress.com introducing a new set of modernized smilies. If you’ve had smilies turned off in WordPress, and have always kept them turned off, then this discussion doesn’t affect you. But for the millions of WordPress sites where content creators have embraced smilies, the community is approaching another interesting fork in the road.
A Bit of Smiley History: WordPress Shows Its Teeth
In order to provide proper context for the current WordPress smilies debate, it’s important to explore a bit of smiley history. The mere mention of changing emoticons has always evoked a visceral reaction from the WordPress community.
Ticket #10145 is home to a five-year-old debate that was recently reignited following the suggestion that core might update to use the new WordPress.com smilies. The ticket proposed that WordPress core replace the old smilies by incorporating a plugin containing what contributor @jdub believed to be “sexier (GPL and Public Domain) smilies from the GNOME and Tango icon themes.”

Without any discussion, the new smilies were unilaterally imposed upon everyone, as outlined in Jeff Chandler’s “Nothing To Smile About,” an account of how the new emoticons ended up in core.
They were added to WordPress.com without any announcement. Users were up in arms over the changes to smilies, lamenting that the new emoticons appeared to be “cheap and cruel” in their expressions. Members described them as “hostile” and “full of teeth.” That support thread is a gem in terms of WordPress smiley history, with several members resorting to verse in order to express dissatisfaction with the new emoticons.
Matt Mullenweg proposed that WordPress revert to the old smilies and instead make it easier for plugin developers to add custom smiley packs.
I suggest we go back to the old smilies in core, and have a canonical plugin for switching smilies that ships with as many open source smiley packs as possible. If we need a filter to do this more elegantly, let’s add it.
The Tango/GNOME smilies were then reverted to the old ones:

As a result, WordPress 2.9, released in December of 2009, introduced the ‘smilies_src‘ filter so plugins could better add custom smilies.
Smiley Wars Part 2: The Demand for Retina Smilies
Ticket #24970 revives the smiley debate, five years later, proposing that WordPress update the emoticons to be suitable for retina displays. Several commenters on the ticket are in favor of using the new WordPress.com smilies, which is already a possibility thanks to a plugin created by Janneke Van Dorpe.
Samuel “Otto” Wood, author of the smilies_src filter patch applied during the Tango/GNOME era, voiced his renewed opposition:
-100 for including them in core. I love my existing smilies and will not be changing them.
If you want to include them as an option and thus add a new configuration setting, sure. But changing the actual content of my site to something else will draw my ire same as it did when you tried it before.
Nothing personal, but these are just as bad as the last time this was attempted. They look *wrong*.
Smilies Are Content
Otto goes on to suggest that if people want the new emoticons, they should be added to Jetpack or another plugin instead of forcing the new designs on WordPress users. He commented:
Like it or not, those smilies are content. If you’re going to change them, you need to make sure you don’t change them on existing content without permission. That tends to tick people off…
What I don’t want is for you to put them in core and thus arbitrarily rewrite the last X years of existing posts I already have to have these hideous new things instead.
Respect the content, respect the history.
The prospect of updating the emoticons means that WordPress users will either be forced to use the new smilies or use a plugin to revert them back.
This debate highlights a hardware difference among WordPress users. Those using devices with retina displays are generally on board with updating the emoticons, since the current ones appear to be blurry. Supporters see new emoticons as a necessity of the modern era. WordPress lead developer Andrew Nacin commented on the benefits of updating the emoticons to a more modern set:
WordPress would benefit from HiDPI smilies. We would also benefit from shipping smilies that were designed in the last decade. But the fact is, there’s a lot of existing buy-in for something to change here. These smilies, if nothing else, provide a strong starting base.
In response to the possibility of core emoticons being up for change, Otto released a new plugin today called Classic Smilies, in order to future-proof content against core changes.
“It seems that to prevent core from stepping on my content I now have no choice but to run preventative-measure plugins like these,” he said. “And that’s just a darned shame, in my opinion.”
Changing Smilies is No Small Thing
The ticket for retina smilies is now home to a hot debate on where WordPress will go next in its support for emoticons. Any proposed changes will affect millions of users. If the Tango/GNOME smilies incident taught us anything, it’s that a healthy community discussion is valuable in understanding the implications of any proposed change.
Big deal, they’re just smiley images, you might say. But smilies have a wider impact than we realize. They’re woven throughout posts and comments as part of a conversation and sometimes provide critical context for a discussion, much in the same way that images/media do. As one WordPress.com user commented five years ago, “Those little niceties can go a long way towards creating a pleasant comment thread.”
A drastic change to smilies affects the tone of previous conversations. One might even argue that changing the face of the emoticons rewrites the history contained in older posts. In some cases this affects 10+ years worth of content. However, the number of years and posts affected doesn’t really matter. The fact is that millions of WordPress blogs are positively riddled with smilies. An update that forcibly changes this content may not be well-received.
But how long can WordPress continue to ship emoticons that appear blurry as technology advances? The advent of retina displays has created an irresistible pull on software to support this technology. Modernizing WordPress for better use on all devices was one of the important factors in 3.8’s updated admin design. In this fast-moving digital age, a sentimental attachment to old designs is a death knell for any software.
It isn’t likely that WordPress will add options for users to choose their smiley package, given its core philosophy of “Decisions, not Options”. Those who oppose updating the smilies to new ones will fight tooth and nail to keep them out, even if that means removing emoticons from the core altogether. How will this community-driven project solve the smiley dilemma?
Why don’t we just recreate the current smilies designs in 2x? Then you’re not completely changing content.