35 Hilarious And Wholesome Bosses Who Made Their Employees Smile, As Shared On This Online Thread

In the modern workplace, a boss who combines humor, kindness, and leadership is a rare and cherished gem. These leaders go beyond meeting corporate goals; they create environments where employees feel valued, motivated, and sometimes even laugh out loud. Whether through small acts of thoughtfulness or big gestures of camaraderie, these bosses prove that a positive workplace culture starts at the top.

Here’s a collection of some wholesome and funny bosses who have gone the extra mile to make their employees’ lives better—and more entertaining.

#1 Alli Had A Very Rough Day At The Animal Hospital – My Employer Found Out And Sent Her A Care Package

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#2 Bro Boss

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#3 Started A New Job 3 Days Ago And I Just Lost A Family Member. This Is How My New Boss Responded. I Couldn’t Be Happier With My Decision To Work For Him. Take Notes, Employers – This Is How It’s Done

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#4 I Asked My Boss If We Could Pose With (Some) Of Our Prop Money At The End Of The Day; He Insisted We Use All Of It

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#5 Yesterday The Owner Of My Company Noticed That The Shoes I Had On Were Worn Through And The Jeans I Had On Had Holes In Them

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I was planning on getting a new pair of each on my next paycheck. Today he took me to Costco and bought me 2 new pairs of shoes, 4 new pairs of jeans, and some food.
I started in December of 2020 after being laid off/unemployed for a vast majority of the year. I’m still trying to get back on my feet financially and make ends meet. It was such an unbelievably nice gesture. I cried and gave him a hug. I can’t wait until I’m able to pay it forward.

#6 My Boss Got A Puppy And Brought Her Into The Office. Productivity Went Waaay Down

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#7 Semi Load Of Water I Just Got To Donate

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I actually work for a company that cares. My boss gave me $10k to help wildfire victims, doesn’t care how it helps as long as it helps. Started with a semi load of bottled water. In 3 decades of work, I’ve never worked for good people until now. Been smiling for 2 days about this.

#8 Beautiful To Be Supported By Such A Thoughtful Team

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#9 The Boss Is Clearly A Micromanager

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#10 Someone Asked The Boss If We Were Going To Have Cake For Halloween, He Disappeared And Came Back With This

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#11 I’m The Only Gothic Person In The Office. Halloween Is My Favourite Time Of The Year. Came To Work To My Desk Decorated For The Day By My Managers

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It was also my birthday earlier this month, but I was on holiday (which is why the desk wasn’t decorated to begin with) so they got me a Halloween themed cake! Don’t think I’ve ever felt this special. Happy Halloween everyone!

#12 Best Boss Ever

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Last week my boss asked me to go over some paperwork for a project, to which I said, I will make it a fun weekend activity to read through it with my son. For context, my wife and I have set a goal to read him 1000 books in 2024. We joked that the paperwork should count as 10 books, we chuckled and moved on. Today, I came in to work to find a couple books and this note with a couple books sitting at my desk. The fact that she cared enough to not only buy the books but to write this adorable note genuinely made me smile. It’s these small details that make her the best boss I have ever had.

#13 Boyfriend Lost His Serving Job Because Of Corona. Bosses Cleared Out The Kitchen To Provide Food For Employees And Intend On Making Them Weekly Care Packages

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#14 The Manager At This Restaraunt Is Breaking Up The Lobster Shells For These Two Old Ladies Who Are Celebrating One Of Their Birthdays

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#15 This Is My Home Office My Whole Team Works Remotely Now Since Covid. Here’s The Shelf Next To The Desk Set Up. Still Need To Get One More Shelf To Complete The Space But I Love It So Much Already!

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#16 Been Battling Mental Health Struggles The Better Part Of My Life And Finally Had A Psychotic Break Last Night And Am Now Seeking Care. Was So Nervous To Text My Supervisor About It. This Was His Response :’)

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#17 Gonna Need To See Those Welds So I Can Pretend I Know A Lot About Welding

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#18 I Jokingly Told My Boss My Basement Level Office Needed A Sky Light. He Made It Happen

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#19 My Boss Writes Notes On His Hand And Photocopies It For Later

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#20 These Were Given To Me By My Indian Boss As Part Of Diwali Celebrations. Sweet And Filled With Cashews

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They’re delicious and I don’t know what to Google to find more.

#21 What A Perfect Response

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#22 My Boss Gave Me My Christmas Gift A Little Early This Year. A Set Of All-Clad Plus A Cuisinart Food Processor!

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#23 My Boss Gifted Me My Dream Car

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The Outback has always been my dream car for the last 10 years. Started out with an Impreza that ended up breaking my heart when the CVT died and I wasn’t in a position to get it fixed. I’d given my wants up to time, if I get it, awesome. If I don’t, I still have a vehicle.

I moved 2k+ miles with just my kitties from the state I grew up in 2021. Will be at my firm 2 years on 04/25. I had a car after the Impreza died, which happened 10 months after I moved, but the Volkswagen had been stolen (then returned 12 hrs later with 7 suitcases and fentanyl in it) and it was really janky and would break down a lot.

My boss saw I had a need and only out of the goodness of his heart fully paid for my ‘21 Outback. No strings. No payments to him. However he is an attorney and made me get an insane 1M policy. But I don’t complain about that at all. I got incredibly lucky as the amazing dealer found one with 1 owner who leased it so, it only had around 18k on it. I have my dream car. 5 months later I still can’t believe it. Absolutely floored. Hard work pays off in other ways than money or promotions.

I’m so eternally grateful for the people the Universe has put in my life. Words can’t explain my appreciation and safety knowing people I have no relation to has my back. And it gives me comfort to know that my closest friends and family to think of me in such a way to see me happy.

#24 Two Years Ago, The Company I Was Working For Was Bought Out And I Lost My Job. My Manager Sent Me This Hand Forged Knife As A Goodbye Present Because He Knew I Collected Knives. It’s One Of The Kindes Gestures I’ve Ever Received

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#25 My Boss Lost A Bet

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#26 Last Day At Work, Boss Got Me A Cake

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#27 My British Boss Is Pretty Pleased With His 4th Of July Outfit

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#28 We Made Our Own Valentine’s Day Boxes For Work. This Is My Boss

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#29 I Don’t Drink Coffee And This Morning My Boss Gave Me A Strange Beverage Simply Labeled As “Ocean” And Now My Brain Feels Like It Has 800 Hp And I Can Also See God

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#30 Gift From The Boss

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I was joking with one of my bosses that when he went to Disney that he should bring me back a lightsaber. He jokingly told me one of the owners is a huge Star Wars guy himself and goes several times a year himself. I started joking with him that he should get me one next time he goes. Turns out he came back yesterday and he gifted me this bad boy today. I offered to throw him money for it but he insisted that I just have it for free. Definitely extremely grateful to my boss for this!

#31 I’d Like One Please

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#32 23 Years Ago, My Boss Gave Me This Ornament Because I Loved To Eat Hot Dogs For Lunch At Work

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#33 Boss Surprised Me With Vegan Cupcakes For My Birthday