Few cartoon characters are more hated than Clippy, the pesky “assistant” who prowled the mean streets of Microsoft Word in the 1990s.  (“You look like you’re writing a letter.” NO I’M NOT FUCK YOU DUDE.)  Clippy is like the Comic Sans of cartoons.  He’s like the primitive ancestor of Siri cross-bred with the Noid.

(By the way, I apologize for gender-stereotyping, but I always assumed Clippy was a guy.  Why this is the case—and why iconic portrayals of later digital assistants like Siri or the operating system in the film Her were presented as female—is a subject for rich speculation.)

Anyway, even if Clippy no longer haunts our lives, the paperclip remains part of the iconography of digital culture.  Most email services use a clip as the symbol for “attaching” a file to an email, whether it’s a document, sound recording, video, or any other type of information.  I did not care to conduct a sweeping survey by registering addresses at a various services to see if this visual choice was universal—certainly, Gmail and Yahoo Mail use it, as does the horrible Outlook client that my university uses.  (Indeed, if anyone out there knows of a platform that uses something other than a paperclip icon, we’d be interested to know.)

I do not know the exact history of the paperclip-attachment nexus—the first attachment was sent in 1992 by scientist Nathaniel Borenstein—but it feels like it is implicitly tied to the metaphor that e-mail is akin to the postal service, or any other letter-carrying business.  The little letter icon appears next to “Send,” with the “Attach” button right beside—implying that whatever .m4a or .doc or .jpg file you’re sending is getting affixed to the envelope that travels to your electronic correspondent.

But then again, who uses a paperclip when mailing a letter or package?  Historians, of course, know that archivists clip documents together in folders.  Perhaps the symbolism is more grounded in the paperwork of office culture, as in simply attaching one document to another (say, a reimbursement request and a receipt).  E-mail, after all, is an example of what media studies scholars Jay David Bolter and Richard Grusin call “remediation”—people often translate and reconstruct the structure of an old medium in a new technological platform.  Television reformatted both the tropes of radio programs and film once it became possible to transmit sounds and images through the airwaves; radio journalism itself picked up the habits and norms of print media when broadcasting first emerged.

Likewise, e-mail in many ways modeled itself after what people already knew of communication and written expression—the metaphorical imagery of a letter literally transmitting over space (even if the process bore little, if any resemblance to the workings of traditional mail); the use of greetings and salutations, like “Hi,” “Dear,” “Sincerely,” and “Best” (even if, as any tormented professor will tell you, the texting generation has dropped all pretense of courtesy in e-mail communication); even the ludicrous rumors that an ailing United States Postal Service was going to start taxing e-mails that popped up periodically in the 1990s and early 2000s.

It is perhaps unworthy of observation to note that people naturally translate what is familiar into new, unfamiliar circumstances, as when any new technology comes on the scene. (When my big sister first helped me set-up an e-mail account in the mid-1990s, I was amazed that it was free. How can you send a message without paying, like with the mail or telephone?)  But I have always had a nagging curiosity about why certain visual and aesthetic choices get made by the designers of technology, and how they worm their way into our minds through everyday use.

For example, why is a paperclip the symbol of “attaching” a file to an e-mail?  Indeed, why is it even called “attaching”?  One could imagine a number of other terms being used.  Perhaps a staple would serve just as well a clip; indeed, just using a clip seems far less secure, like your item could easily come loose and float away. (I definitely thought about this prospect when sending a huge sheaf of documents to the IRS the other day.)  When you absolutely, positively have to get the job done, use a staple.

Of course, these aesthetics become secondhand over years and everyone takes them for granted.  Or do they?  I have so often found myself going to click the “link” button on Gmail when I mean to attach a document.  The icon for embedding a link, of course, is a chain. Perhaps this mental quirk is unique and meaningless. But there is definitely something in the brain that says, “I want to connect this to this”—this .doc file to this electronic message.  A chain is a symbol of connection, for sure, if not always in the best way. It bears the negative connotation of imprisonment or slavery; shackles don’t instill confidence in the user experience.

But a chain can also be positive—a gold chain, or as a symbol of unity and strength—there is, of course, the old adage that a chain is only as strong as its weakest link. If you wanted to make sure something did not get lost, you might prefer a chain to a paperclip.

In short, why do we think of attaching a file in terms of a clip—something loose and temporary—while we think of embedding a link as chaining something to something else?  Certainly the term makes sense (a chain is made of links, after all), but is our mental image of the Internet essentially a lot of things connected by chains—in a sense, a great chain of chains? (Remember former Sen. Ted Stevens oft-mocked assertion that the Internet was “a series of tubes.” For what it’s worth, I doubt that the venerable late Senator had a much worse understanding of the way the Internet works than the wizened members of the Supreme Court, who make consequential and far-reaching decisions about technologies such as Napster and ReDigi all the time—let alone the general public.)

No, the Internet does not seem to share a gestalt with an S&M sex party that got badly out of hand.  Indeed, ever since Tim Berners-Lee revolutionized how people used digital communication with the World Wide Web in 1989, we have thought in terms of webs and nets—a supple, flexible matrix of connections, not a chain of interlocking iron links. (The novelist Peter Ackroyd hilariously lampooned the culture of the twentieth and twenty-first century in his futuristic satire The Plato Papers, as a historian in the year 3700 looks back on our epoch, known as the “Age of Mouldwarp,” when people apparently spent their days covered in webs and nets. “They seem to have worn these dismal garments as a form of enslavement as well as worship…”)

For me, all these questions crystallized recently when I was attempting to CC several administrators and faculty on an email. Instinctively, I went to hit the “attach” button when I meant to add another person’s email address to the message.  Of course, no one attaches a coworker to an email, but that unthinking movement seemed to come naturally.  You’re adding someone to something, forming an association or connection—but the paperclip is obviously not the right icon.

It’s “carbon copy,” another holdover from written or print culture that feels almost endearingly antique in 2016.  From a time before the Xerox machine, when the best choice available to duplicate a message was to make a messy, fuzzy impression of what one wrote or typed, we still use the same language for an electronic message about scheduling a meeting or filing paperwork (which, itself, might not actually be paper anymore).

These choices are arbitrary, occasionally cute, and often annoying. (Hello again, Clippy; he recently made a cameo in an episode of HBO’s Silicon Valley as the avatar of bad corporate design thinking.) But I wonder what these symbols mean to us—why they get picked at pivotal moments in the development of software or an interface, and how their implications come to be as commonplace as water.  You attach a file with a paperclip, you embed—there’s another interesting, unexamined word—a link with a chain.  You carbon-copy a friend or coworker, as if sending an email to multiple people makes multiple copies.  We do not think of a broadcast or a robocall making “copies,” though in some sense the effect is similar.

A chain is stronger than a clip, implying that the connection between links is stronger than that between a message and an attachment.  Given a different history or a few different critical choices, we might have thought in terms of other metaphors—tying, taping, gluing, affixing, even embroidering connections from one thing to the next. I won’t hold my breath, though, for the idea of bedazzling an email or webpage with links catching on.

Editor’s note: if you find this to be pointless navel-gazing, we only sort of care. Also, we blame Gaston Bachelard generally, and his book The Poetics of Space more specifically, for the whole thing.