10 Most Awkward Moments in The Office That Made Us Cringe

From an emotional rendition of “525,600” minutes, adapted from Rent to how long Michael Scott (Steve Carell) worked at Dunder-Mifflin, to Dwight (Rainn Wilson) suffering in silence over being passed over as the next host of the Dundies, “Michael’s Final Dundies” hits emotional highs and cringe moments. When Jim (John Krasinski) forgets to mention Pam (Jenna Fischer) at the Dundies that night, it makes everyone feel just a little awkward, then Dwight makes it worse.

Then, just as with the original Dundies, the awards take a turn and start to include “Worst Salesman of the Year,” “Extreme Repulsivness,” and “Diabetes Award.” It’s fitting that Michael leaves just as awkwardly as he was introduced to the audience, and no amount of character growth over five seasons will smooth out all the socially inappropriate edges.

When Robert California (James Spader) says he’s selling his massive home, the decision is made to have a pool party before it goes, and the result is a night of awkwardness for the characters and the viewers. The Office, after Steve Carell left, had trouble finding its footing, but through Erin (Elle Kemper), the awkwardness never left.

In an attempt to make Andy (Ed Helms) feel jealous, Erin flirts with Dwight all night, a plan he’s far too willing to get on board with. Until a chicken fight goes horribly wrong and he nearly dies in the pool. It only gets worse when the cellar is cracked open and the staff of Dunder-Mifflin gets drunk together, resulting in awkward conversations and brutal truths.

“Did I Stutter?” centers around Stanley (Leslie David Baker) finally snapping back against Michael during an already awkward meeting. Michael can’t handle the pushback and spends the rest of the episode unsure how to react, which is a small plot with no real stakes, but to anyone that has to work, it’s immediately relatable.

There’s no other major moments in the episode, but the entire runtime after the confrontation is one long cringe moment. The Office works best when the plots are small and relatable, and though Michael tries to “fake fire” Stanley at one point, the awkwardness of his constant misunderstandings of the situation keep making things worse and worse.

“The Golden Ticket” is about Michael’s poorly thought-out promotion, which is exceedingly cringy because of the very relatable end result. Since each ticket is good for 10 percent off, and Michael put all five in the same part of the warehouse, their biggest client gets all of them, for 50 percent off in total.

Ever have a boss that thinks something is a perfect idea, and it goes horribly wrong? That’s why this episode of The Office is painful to watch because that’s exactly what happens. It’s so bad that Kevin dropping a wildly inappropriate comment towards a co-worker is the least cringe part of the episode.

Making “Diversity Day” the second episode of The Office was a gusty call, right up there with It’s Always Sunny In Philadelphia, starting with “The Gang Gets Racist.” After Michael repeats a famous Chris Rock stand-up bit, you know the one, Dunder-Mifflin is visited by a consultant (Larry Wilmore), and he doesn’t end up fixing anything.

The worst moment comes when Michael has the staff wear index cards with different ethnic groups on them and asks everyone to imitate the group so that the card-wearer can guess the ethnic group, ending with an insulting Indian stereotype in front of Kelly (Mindy Kaling), who wasn’t actually wearing a card. Even after the series finished its run, “Diversity Day” remained one of the most cringy episodes of all time.

When Andy brings his college acapella group, Here Comes Treble, to Dunder-Mifflin, he hopes that they ask him up to sing George Michael’s “Faith.” In classic The Office fashion, the initial cringe from Pam being serenaded while fighting with Jim is overshadowed by Andy losing his cool over the revelation that Broccoli Rob (Steve Colbert) is known as “Boner Champ,” and “Faith” is his signature song.

The poor college students present, by their facial expressions alone, want to be anywhere else than in a room with Andy. Acapella drama is some of the lowest stakes ever on the show, making it even harder to handle Andy’s surprisingly strong feelings.

An entire episode of cringe, “Phyllis’ Wedding,” is a nonstop series of awkward Michael Scott moments. From asking if she “broke wind,” to announcing the end of the wedding himself, Michael keeps making things worse for Phyllis, and the viewers. The worst moment, out of many, is accusing her dad of upstaging him.

Or maybe it’s smashing the wedding cake into his own face at the very end, though it could also be the traumatic recollection of acting as a ringbearer as a kid. The wedding speech is also an option, as this episode of The Office is 22 minutes of cringe.

In “Broke,” after Michael, Pam, and Ryan (B.J. Novak) realize their new company isn’t making any money, they’re forced to negotiate for their jobs with Dunder-Mifflin. Michael stands strong against a cash offer and engages in verbal warfare to make sure Ryan and Pam have jobs to go back to. In a surprisingly tense scene for The Office, it goes beyond the usual level of cringe and becomes about people fighting for their jobs and livelihoods.

In that moment, The Office again becomes real, and while Michael’s speech about the real value of his business is idealistic, who hasn’t been present when a co-worker tries to give a profound speech and wanted to be anywhere else at the moment?

A delightfully awkward episode, “Dinner Party” was the first episode to air of The Office following the 2007 writers’ strike, and it was an immediate classic. When Michael invites the couples, Jim and Pam, Andy and Angela, to join him and Jan (Melora Hardin) for a dinner party, it starts cringy and only escalates.

From seeing Michael’s living conditions to Jan’s playing of an intimate song by her former assistant, the episode slowly ramps up the cringe; finally, the police get involved in responding to a “domestic disturbance” that occurs when a Dundie is used to break a TV. Jim and Pam are the audience, desperately trying to escape an awkward situation but unable to get away until its too late.

The one episode of The Office that is so cringe-worthy die-hard fans skip it while binging, “Scott’s Tots” is the most awkward episode of television ever filmed. The revelation that Michael promised an entire third-grade class he’d pay for their college education is paid off when the class, now seniors in high school, launch a celebration for Michael.

Michael knows he can’t pay the tuition and will have to renege on his promise, but yet, between the speeches and tribute rap, he has moments of feeling like he deserves the praise. Steve Carell’s facial expressions, from awkwardness to pride, to right back to wishing the Earth would open up and get him out of the classroom, make it a hilarious and cringy experience. Not just the most cringe-worthy episode of The Office, but of all television, “Scott’s Tots” is hilariously hard to watch.