While it was nearly impossible to compile a list this brief, here is our collection of 10 moments from The Office so embarrassing that the audience cringes in solidarity along with the characters.

10- Michael’s Racist Conversation with Kelly Diversity Day (Season 1, Episode 2)

It may only be the second episode of the series, but Michael’s failed attempt at leading the Scranton branch in sensitivity training is well remembered. After offending people with a Chris Rock comedy routine, Michael and the rest of the office must undergo sensitivity training. Michael, needing to prove that he is the most sensitive of all, sets out with the best of intentions, but instead creates offensive moment after offensive moment. The episode comes to a peak as he speaks to Kelly in a very racist specific accent.

Ranking The Office Halloween Episodes

9- Toby Touches Pam’s Knee in Night Out (Season 4, Episode 15)

Me watching this scene- (Hand over mouth) “Toby, what are you doing?!?!” EVERY. DAMN. TIME. Toby handles his instant regret of an awkwardness bomb by announcing that he’s moving to Costa Rica, abandons his car, hops a large fence, and jogs home.

8- Jim Gets Put in the Middle of Robert and Andy in Mrs. California (Season 8, Episode 9)

Yes, I included something post-Michael from The Office. For those of you who stopped watching after Michael Left, Robert California was the very intimidating, and often confusing, CEO of Sabre: the company that purchases Dunder Mifflin. He places Andy in a difficult spot when he informed him that his wife wanted to work there, but under no circumstance was he to hire her. All the while, Robert encourages his wife and tries to strong arm Andy into hiring her. A confused Andy and an angry Robert look to Jim to sort out what was and was not said directly in front of Mrs. California. Jim, however, goes into hiding and is forcibly dragged into the conference room to have a very uncomfortable conversation.

The Office gets its own version of Clue

7- Jan Listens to Michael’s Break-Up Voicemail In-front of him (Season 3, Episode 22)

In Women’s Appreciation, Michael takes the ladies of Scranton to the mall for lunch and a chat. After revealing how much he does not enjoy being with Jan, the girls empower Michael to break up with her. So, Michael does what any sensible gentleman would do: breaks up with her via voicemail. Jan walks in just as Michael finishes recording, sees that she has a voicemail, and begins to listen to it as she discusses dinner plans with him. Cue uncomfortable shifting in seat…

6- Kevin’s Attempt at an Inspirational Speech in The Seminar (Season 7, Episode 14)

Kevin tries so hard to help Andy out when Jim bails on his small business seminar. He creates a grand entrance complete with running and rock music, and delivers attempts to deliver an inspirational speech about achieving your dreams. Kevin unfortunately runs a bit too much, can’t catch his breath, falls to the ground, and vomits all while delivering his message. This is almost as heartbreaking as when he drops his famous chili…

5- Pam’s Accidental Pregnancy Reveal in Niagara Pt. 1 (Season 6, Episode 4)

Pam and Jim make it very clear to their friends and family that her pregnancy must remain a secret from her very conservative grandmother until after the wedding. At the tail end of a beautiful speech declaring how much he loves his bride-to-be, Jim mistakenly asks everyone to raise their glasses except for Pam “for obvious reasons.” Instantly, Pam’s grandmother catches this and asks why she cannot drink. Jim stumbles, calling Pam an alcoholic, and then is “saved” by Michael who babbles on about sex with and without condoms. “To waiting!”

4- Andy’s Cellphone in Andy’s Play (Season 7, Episode 3)

Is there anything more embarrassing than your cellphone ringing when you are attending a show? How about your cellphone ringing while you are on stage… in your pocket… with the ringer on… twice? And then awkwardly trying to improvise and make it part of the show, but actually ruining ongoing plot points?

Own all 9 seasons of The Office in one shiny collection.

3- Michael’s Meltdown in New Boss (Season 5, Episode 20)

Michael becomes so flustered with his new boss, Charles, that he actually starts repeating everything he says in front of all of the employees. The Dunder Mifflin employees, along with most viewers, beg him to stop due to embarrassment through sheer osmosis. As Pam says, “I can tell Michael’s mood by which comedy routine he chooses to do. The more infantile, the more upset he is. And he just skipped the Ace Ventura talking butt thing…This is bad.”

2- Dinner Party (Season 4, Episode 13)

The best My personal favorite episode of the series pulls the audience in to experience the world’s most awkward dinner party. This 22-minute episode is noticeably darker in its comedic choices than the rest of the series – a risk that paid off big time. It’s hard to not look away as we go further down the rabbit hole of Michael and Jan’s unraveling relationship, discovering the emotional toll that 3 vasectomies can have on a person, veiled threats, fights, guests failed attempts at ducking out of the whole event, and more. Hunter’s song (Jan thinks he’s very talented) sums up this episode best: “So raw, so right, all night, all right, oh yeah.”

1- Every Stress-Inducing Minute of Scott’s Tots (Season 6, Episode 12)

If you’ve seen the series, this should come as no surprise. Scott’s Tots stands out among fans as one of the most cringe-worthy episodes of any television show ever made. It is not uncommon to skip this episode when re-watching the series because it is that uncomfortable to get through. 10 years in the making, Michael Scott promised a classroom of elementary students that if they could make it to graduation and get into college he would cover their tuition. As a Dunder Mifflin Regional Manager, Michael can barely afford his condo. The entire episode places layer after layer of awkwardness building towards Michael needing to come clean after being celebrated as a great philanthropist. It’s something that you must see to believe.

Elizabeth Sanderson is a teacher, musician, and board gamer extraordinaire. She is eagerly awaiting her birthright to appear in a Hocus Pocus reboot and is currently rewatching The Office for the 15th time.

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