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Boss Orders Employee To Smile More, Gets Creepy Grin That Haunts The Office!

by Annie Nguyen
October 28, 2025
in Social Issues

Navigating a new boss’s expectations is tough, especially when they seem to have it out for you. At a major insurance company, one tech support employee, valued for their humor and rapport with colleagues, faced a new manager whose abrasive style and personal bias disrupted the team’s harmony.

When the manager called them out for not smiling enough during a review, complete with a condescending demonstration, it sparked a bold move that shook up the workplace. Scroll down to discover how this employee turned the tables.

One Redditor faced a new manager’s wrath when he demanded she smile more during an employee review

Boss Orders Employee To Smile More, Gets Creepy Grin That Haunts The Office!
Not the actual photo

I was told I needed to “smile more”, ok then

I worked as a tech support for a global insurance company with three big letters.

Our old manager retired, a cool guy, not a micromanager.

We get this new one who was, right away, very confrontational.

He was a my way or the highway kind of guy, even when we explained the bureaucracy of our company and processes.

For whatever reason, he had it in for me, went as far as making comments in front of everybody about replacing me.

At one of our employee review meetings, he said he was getting complaints of me “not smiling enough,”

which I found very odd because I consider myself a likable person.

I’m always joking with other users and employees, which I’ve found helps with the job.

So he continues and even goes as far as to show me how to smile.

Cue the malicious compliance.

I proceed to give out the most forced,

creepy smile humanly possible every time I interact with a user, every single time.

People asked me what was wrong, and I always answered,

“Following an employee review, I was instructed to smile more, so I’m smiling.”

I was doing this for like a couple of days,

and after an interaction providing support for Human Resources

with a smile and explanation, I went back to my desk.

Couple of minutes later, I saw the HR lady go to my boss’s office; they were there for like half an hour.

After she leaves, the boss calls me in, and tells me I don’t have to smile anymore.

I respond sarcastically with, “Aww do I really have to stop?”

He looks at me and tells me that’s all.

He left like a year later; no one, not even the other managers, liked him.

Micromanagement and inappropriate workplace demands, like the manager’s insistence that a tech support employee smile more, can create a toxic work environment.

The employee, known for their humor and likability, faced unwarranted criticism from a new, confrontational manager who dismissed their contributions and even demonstrated how to smile during a review.

This not only humiliated the employee but also ignored their effective customer interactions, highlighting a broader issue of misguided leadership.

Such demands often reflect a manager’s attempt to exert control rather than foster productivity.

According to Harvard Business Review, micromanaging behaviors, like dictating personal expressions, erode trust and morale, leading to disengagement or resistance, as seen in the employee’s exaggerated, unsettling smiles.

The Reddit comments echo this, with users sharing similar experiences of being pressured to smile despite personal or professional challenges, underscoring the demand’s insensitivity.

The employee’s response, a form of malicious compliance, exposed the absurdity of the directive.

Organizational psychologist Dr. Amy Edmondson notes that such actions often arise when employees feel undervalued, using compliance to highlight flawed policies without direct confrontation.

Here, the employee’s exaggerated smiles prompted an HR intervention, illustrating how poorly judged demands can backfire when clients or colleagues react negatively.

Workplace policies should prioritize respect and focus on job performance over superficial traits.

The Society for Human Resource Management advises that feedback must be specific, job-related, and constructive to avoid alienating talent.

For employees facing similar situations, documenting incidents and escalating concerns to HR, as the employee indirectly did, is effective. They should also review company policies to understand their rights.

Managers must foster open communication, focusing on measurable outcomes rather than personal demeanor.

In this case, the manager’s departure suggests broader disapproval, but proactive training and clear policies could prevent such conflicts, ensuring a workplace where respect drives performance, not arbitrary demands.

Here’s what Redditors had to say:

These Redditors shared stories of being told to smile despite personal struggles, slamming such demands

BbyAngeleyez1226 − I hated when people told me to smile more when I worked at my night shift coffee drive thru.

One guy said "you know, if you smile more, you'll get better tips."

At the time I was going to college during the day, freshly lost my mother to cancer and working nights full time. I replied with, "

you know, you should say that to your wife and have her make your coffee then."

He never said anything about me smiling again, and he started tipping the night shift staff.

NikkiCanada − I get told to smile more all the time, but honestly, after my son died three years ago,

I find it really hard to smile anymore. So, people who tell strangers this, please stop!

It may be a nice gesture in your world, but for some of us who struggle just to get up every day

and do the basic functions to exist, we don't care for it.

I'm sure there are very good intentions behind them, saying that

but please just let me be angry with the world in peace, thank you

AccentFiend − I have RBF. I'm also constantly cracking jokes to friends and laughing.

As a female, the number of times I've had a male tell me something along the lines of "you have a beautiful smile

you should use it more often" is countless. And there's no good response to it.

What, do you want my now VERY awkward smile?

Do you want me to thank you for your backhanded compliment?

Should I throw myself at your feet, sobbing in silent gratitude that you've acknowledged my existence

so you feel you've done a good deed? I started responding. "Well, give me something to smile about, then." Deadpan.

Dead look in my eyes. Not even an eye twitch. NOW who's smiling awkwardly? Stammering?

Or they get indignant, and then I just laugh and say something like "rude, isn't it?" No regrets.

This group defied “smile more” orders with sarcasm or deadpan stares, relishing the awkwardness

QueenMidnightWolf − When I was working in customer service at a grocery store

I absolutely hated when people told me, "You need to smile more" or "you'd look so much more beautiful if you smiled".

A few times during covid when masks were mandatory customers still said, "I don't see you smiling".

So what did I do? I closed my eyes, tilted my head a bit, and drew an imaginary smile over my mask.

Do I have a resting b__ch face? Yes. Does that mean that most times I'm in a bad mood?

Depends. Am I going to work on fixing my resting b__ch face?

No. Because it keeps most strangers from approaching me when I'm out in public.

bearandtherats − My favorite is when old white men tell me "you'd be prettier if you smiled".

I always tell them that they would look smarter with their mouth shut.

dr-sparkle − I like to either look them in the eye and say "I AM smiling"

and maintain eye contact until they go away or do the "m__der" smile.

These users recounted creepy compliance or bosses being called out for policing expressions

dropshortreaver − About a decade ago, I worked as a Security guard at a big name British supermarket.

The company actually had two types of guards, their own internal security who(other)manned the CCTV out the back

and did LP in the store and uniformed Security guards (Contractors), like me.

Who stood at the entrances whose basic job was to be visible, check receipts when the anti theft scanners went off

and occaisionly stop shoplifters as they exited when the CCTV had caught them.

They used to insist we had to do the same internal training courses as their own staff.

One of these was a customer service course, where one of the suggested activities would be for everyone on the course to go to the main entrance

and stand outside waving and smiling to people as they entered.

I pointed out we were ALL noticeably wearing uniforms with Security written all over them

and that personally if I went to a Shop and saw about 10 Security guards waiting outside the entrance smiling

and waving would turn around and leave thinking something major was about to go down.

lura66 − I was working in a large office with a ton of people and this one older guy was OBSESSED with me smiling more.

He wasn't my boss, nor even a colleague. He was essentially a client that worked within the office.

He complained and complained about me smiling constantly.

My boss caved to this man's demands and was always telling me I needed to smile. This pissed me off for two reasons.

I was in the middle of having major dental problems and was having a major procedure or surgery on my mouth

about once a month or so at that point. I had very limited movement there, and my boss knew that.

He was one client out of 300. Not one other client ever mentioned it at all.

Well I did smile at him after while, creepy just like you did.

But one day I was distracted and didn't notice him walk in, and he went full on lecture about me smiling.

One of his favorite points was "It is just rude and unbecoming of a young lady to not smile"

The owner (my big boss) happen to walk in behind him and he didn't notice because he was too busy being a d__k.

She let him finish, then made herself known and said, "I find men trying to control a woman a third of their age really unbecoming and rude."

He never spoke another word about the smile. I worked there for another year and never once smiled at him again

and I could just see how much it killed him not to say anything. Eventually, he just avoided m,e and I was A-ok with that!

These Redditors mocked the absurdity of smile demands, citing physical or emotional barriers

SordoCrabs − "Gosh, I'd love to stop, but my mom was right about making faces and now it's stuck this way."

GottaLoveHim − We had a family member that had some kind of nerve damage in her mouth/face

and she could NOT smile. People could be so rude - was she supposed to wear a sign? ??

These users criticized workplace smile mandates, suggesting HR intervention for toxic bosses

Murky_waters13 − I've always hated this, 'you should smile more.' 'Smile, it's not that bad.' 'won't k__l you to smile.' A few times my response was, why! ?

Look around you whooo tf is smiling right now? No one.

No one walks around smiling all the time, it's creepy. Find me one, right now and I will smile all you want.

Stabbmaster − Glad he ended up leaving, the "talking about getting rid of you in front of others" bit would have been enough for me to open a case with...

The Redditor’s tale of turning a boss’s smile demand into a creepy office legend is pure workplace gold. Was her over-the-top grin a stroke of genius, or did it risk escalating the drama?

Should employees fake cheer to keep the peace, or is pushing back with petty compliance the way to go? Share your hot takes below. This story of office rebellion deserves a round of applause or a heated debate!

Annie Nguyen

Annie Nguyen

Hi, I'm Annie Nguyen. I'm a freelance writer and editor for Daily Highlight with experience across lifestyle, wellness, and personal growth publications. Living in San Francisco gives me endless inspiration, from cozy coffee shop corners to weekend hikes along the coast. Thanks for reading!

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