Embarrassing moments are an inevitable part of life. Whether you realized after getting home from a first date that you had spinach in your teeth the whole time or you accidentally sent your father a spicy text meant for your partner, we’ve all been there. But these awkward moments can be even more painful when they happen in professional settings.
Bored Panda has searched far and wide and gathered photos of the most mortifying interactions that have occurred between bosses and employees. I’ll warn you right now, pandas, that this list will probably give you second-hand embarrassment. But enjoy scrolling through these painfully awkward pics, and keep reading to find conversations with Ekta Capoor, Co-Founder and Editor-in-Chief of Amazing Workplaces, and Career Coach Dr. Twanna Carter!
#1 Such A Worthy Memory

Image source: afaang_
#2 The Look Of Pure Potato Sadness

Image source: PettyClegg
#3 What I’m Hearing Is That You Should Be The Boss Instead Of Someone Flustered By Arrows

Image source: TheLilyLester
#4 It’s Pretty Funny

Image source: PaxBiggs
#5 Work Just Got Very Interesting

Image source: Cherrybomb1993
#6 Oops

Image source: Twelvyyyyyyyy
#7 This Is The Correct Response

Image source: Marshall__Scott
#8 Hope They Felt Really Awkward

Image source: OutofstpmaineAF
#9 At Least You Didn’t Get Fired

Image source: _claudiapolanco
#10 Respect The Honesty

Image source: billybrizzle420
#11 I Accidentally Told My Boss To “Come Grab My Meat” Instead Of My Wife

Image source: thebluevanman73
#12 There Was An Attempt To Text An Old Boss Of Mine, Professionally

Image source: rehabforcandy
#13 Boss Got Locked In His Office And A Section Of The Wall Had To Be Cut Out

Image source: thowitawaypeese
#14 Accidentally Reported My Bowel Movements To My Boss Instead Of My Girlfriend

Image source: Bennybyrnes
#15 There Was An Attempt To Get A New Job

Image source: Sapionist
#16 Yikes

Image source: jamill_steezy
#17 Boss Is Probably Freaked Out

Image source: atdanwhite
#18 A New Guy At The Company Accidentally Sent These Texts To His Manager

Image source: Time_Advisor4822
#19 Subtle

Image source: A_gligs
#20 This Is Really Awkward

Image source: LukeMones
#21 That Awkward Moment When You Accidentally Ask Your Boss For A Hookup

Image source: ShakesSpear
#22 So My Boss Kept Asking Why His Battery Was Running Out So Fast. He’s Pretty Much Had The Stopwatch Running Since He Got The Phone. 631 Days

Image source: Nightspade
#23 Zoom Meeting

Image source: myungbug
#24 Text From My Boss

Image source: senti_naro
#25 Insane Boss Story

Image source: RyanLostinTX
#26 Nothing Like A Sincere Apology

Image source: Barphbie
#27 Insane Boss Story

Image source: vaughnbroadnax
#28 Sending A Text To The Wrong Person

Image source: ChrisIsFantastic, GoHeadBlockMe
#29 Unbelievable

Image source: jenilane29
#30 This Wins

Image source: daberhasher
#31 Insane Boss Story

Image source: KatieSSanders
#32 There Was An Attempt To Check In With My Boss

Image source: 42words
#33 Well. I’m Sure That Was Great For My Friend’s Coworkers And Bosses To All See

Image source: moumou122
#34 Been Working My Butt Off For Over A Year At Work In Hopes Of Getting A Management Opportunity This Summer And Just Received This Text Message From My Boss

Image source: phoxious
#35 Started A New Job Today And My Teenager Had The Computer Before Me. I Opened It In Front Of My New Boss

Image source: Wldhorscodntkepmeawa
#36 Boss Just Sent Me This Text Twice. Shouldn’t Make Things Awkward I’m Sure

Image source: kGibbs
#37 That’s No Way

Image source: momofemcel
#38 This Is A Valid Reason

Image source: johnsiyawajr
#39 Oh, To Be A Boss, Not Knowing How Anything Works, And Still Earn More Than Anyone Else

Image source: MeekyBlinders
#40 That Is Unfortunate

Image source: 2bkomfykozy
#41 Left My Boss A Birthday Cake. The Tube Of Frosting I Was Writing With Broke So I Squiggled On There. Now I Have To Have A Meeting With My Boss And Union Rep To See If I Was Drunk At Work

Image source: reddit.com
#42 There Was An Attempt By My Significant Other’s Korean Boss To Get A Cake That Says “Happy Birthday Hong”

Image source: heritagepilot
#43 I’m Sorry The “Hehe” Made Me Fall Over

Image source: fcksighmoan
#44 The Lecture After

Image source: keeiir
#45 Got A Phone (Didn’t Have One). Texted My Boss To Verify I Had The Right Number And This. I Didn’t Know

Image source: oodlesofschmoodles
#46 At Least He Knows What The Meme Means

Image source: MUSlCALKORDEI
#47 That’s Awkward

Image source: zozyjh
#48 He Probably Did Need It

Image source: jaredadairbell
#49 My Boss Texted Me This. Just Thought This Was Funny

Image source: Correct_Luck3831
#50 When The Hot Straight Boss Sends Me A Rude Email On The Weekend

Image source: TN_GA_Bromo
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