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From Eggplants to Lawsuits: Are Your Emojis Jeopardizing Your Job?

Once upon a time, in the not-so-distant past, emojis were the domain of casual chats among friends, a fun way to add a splash of emotion or humor to our digital conversations. Fast forward to today, and these colorful symbols have infiltrated our digital lives, including the once-staid realm of professional communication. But as we've come to discover, this transition is not without its pitfalls and costly repercussions, including litigation. 

Take, for example, the tale of a significant investor in Bed Bath & Beyond, who, with the seemingly simple inclusion of a side-eyed moon emoji in a tweet, found himself entangled in a lawsuit accusing him of securities fraud. The emoji was interpreted to mean the stock was “going to the moon,” according to a story in The Atlantic. The investor’s attorney was quoted: “There is no way to establish objectively the truth or falsity of a tiny lunar cartoon.”

To make things more confusing, emojis may display differently, depending on the platform, according to

Viewed on desktop, the emoji in the investor's original tweet on X appears as a yellow face emoji with a slight smile, but when hovering a mouse over the emoji, X describes the image as a "full moon emoji." On an iPhone and in WhatsApp, a full moon face appears with eyes looking to the left, giving a "side eye," whereas on Android devices, the full moon face may appear more like a yellow smiling face.


The meaning depends on what you see and how you interpret it, and that can diverge from what the sender intended. A slight smile indicates tepid happiness. A side-eye full moon face emoji can be a swap for a smiley face, can denote embarrassment, or can be interpreted to mean awe and excitement. 

Tiny cartoons come with big risks, because they’re vague and do not carry the clarity of words. Consider: 

Legal Recognition: With hundreds of active legal cases in the U.S. involving emojis, it’s become increasingly clear that smiley faces can quickly turn into frowns. They can convey everything from friendship and happiness to aggression and fear. Courts are taking them seriously, recognizing their potential to convey specific, impactful messages. The side-eyed moon emoji's role in the ongoing shareholder lawsuit underscores the growing understanding that these symbols can carry weighty implications. 

Corporate Communication Shifts: When OpenAI briefly fired its CEO Sam Altman, employees reportedly posted a “f— you” emoji on Slack. When approvals were needed for multimillion-dollar payments at the cryptocurrency exchange FTX founded by Sam Bankman-Fried, supervisors responded favorably with their personalized emojis, according to a Wall Street Journal story. Bankman-Fried is now in jail for fraud. 

The Challenge of Ambiguity: Emojis can be a minefield of misinterpretation, with their meanings varying across different devices, cultures, demographics, and personal interpretations. This ambiguity can lead to misunderstandings in professional exchanges, complicating the evaluation of intent and meaning in legal contexts.

From Silly to Sexting: The impact of emojis on perceptions of professionalism cannot be understated. A text with a peach or eggplant carries overt sexual connotations. Emojis such as a beer mug may be fun to some, but are inappropriate to others. Same for the poop emoji, hand gesture emojis, and countless others. Sexual harassment cases and claims have centered around messages involving winking emojis, dinner plates, and dripping water. 

As emojis cement their place in our professional lives, it's essential to tread carefully and consider context, clarity, and what you are trying to communicate. Ask yourself: Will this come across as respectful and appropriate? How will this be received? Remember, reflect before you hit send, and wield your emojis wisely — if you use them at all. 

Julian Guthrie is the CEO and Founder of Alphy.

Reflect AI by Alphy is an AI communication compliance solution that detects and flags language that is harmful, unlawful, and unethical in digital communication. Alphy was founded to reduce the risk of litigation from harmful and discriminatory communication while helping employees communicate more effectively.


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