By
Updated 2 weeks ago,April 15, 2025
If ever a show perfected the use of cringe comedy, it would have to be the cult favorite NBC series,The Office.
Spanning nine seasons of ceaselessly entertaining storylines,The Officecontinuously drew on a distinct idiosyncratic sense of humor that mainstream audiences instantly fell in love with.
However, its also no secret thatThe Offices showrunners occasionally went abittoo far in their comedic subject matter, inducing as many groans of embarrassment as it did avid laughter from viewers.
The Office
From awkward wedding ceremonies to uncomfortable dinner parties, here are some of the cringiest moments inThe Office,ranked from humiliating to practically unwatchable.
Michael Nearly Derails Phylliss Wedding (Season 3, Episode 16)
Leave it to Michael Scott to very nearly ruin a wedding by throwing a temper tantrum like some melodramatic 9-year-old child.
While everyone else can only express amazement and admiration as Phylliss father pushes himself out of his wheelchair to personally walk his daughter down the aisle, Michael stubbornly refuses to pass up his golden moment, dragging the empty wheelchair with him to the altar and forcefully inserting himself amidst Bob Vances groomsmen.
If that werent bad enough, he then proceeds to unsuccessfully steal the spotlight once again by proclaiming Phyllis and Bob Vance as officially married beforethe minister can declare them an official couple.
Talk about going from bad to worse…
Michaels Botched Marriage Proposal (Season 3, Episode 6)
Say what you will about Michaels antics in the earliest seasons ofThe Office,butno onedeserves the treatment he received in season 3s Diwali.
Caught up in the festivities of Kellys Diwali celebration, Michael makes a spur-of-the-moment decision to propose to his short-lived girlfriend, Carol, in front of the teeming party guests.
Though a romantic gesture in and of itself, the fact that he and Carol had only gone on nine dates together should have been a clear sign that he was moving a little too quickly, culminating in Carol awkwardly asking to speak to Michael in private rather than uttering yes to his proposal.
Michael Tries to Kiss Pam (Season 3, Episode 6)
Whats worse than having your significant other shoot down your marriage proposal in front of your coworkers and a bunch of strangers?
Hmm, its difficult to say, but well go with having your receptionist deny your romantic passes immediately after the fact.
Though the scene starts off normal enough, Michael characteristically manages to ruin his emotional heart-to-heart with Pam through an ill-advised attempt at a kiss.
In a night filled with heartbreak and heartache, this was just one more embarrassing incident Michael had to deal with over the course of Diwalis cringe-inducing runtime.
Jim and Pams Dojo Disaster (Season 2, Episode 6)
Sure, Jim and Pam had plenty of adorable moments flirting with each other throughoutThe Office, but season twos The Fight isdefinitelynot one of them.
As they await Dwight and Michaels karate showdown in Dwights dojo, Jim and Pam get a bit physical on their own, leading to Jim accidentally exposing some of Pams midriff in front of her coworkers (much to Pams shock and embarrassment).
In a season filled with plenty of romantic back-and-forth interactions between these two, this brief scene in The Fight is enough to make every viewer who shipped Jim and Pams relationship absolutely mortified.
Michael and Jan Ruin Their Dinner Party (Season 4, Episode 13)
Say what you will about Scotts Tots, but at least that now infamous scene doesnt span an entire episode.
The moment Jim and Pam arrive at Michaels humble abode in Dinner Party, however, viewers cant help but instinctively start to tense up from sheer discomfort.
Of course, it doesnt get any better the longer the night draws on, with Jim perfectly summing up his hosts recurring arguments: Michael and Jan seem to be playing their own separate game, and its called Lets See How Uncomfortable We Can Make Our Guests?
Watching the finished episode including Michael and Jans awkward house tour and their full-blown shouting match over dinner its hard to argue against Jims highly accurate assessment.
Toby Touches Pams Leg (Season 4, Episode 15)
Ironically, one of the most painful moments ofThe Officedoesnt involve Michael at all, but instead focuses on his one-sided nemesis, Toby Flenderson.
Trapped inside the Dunder Mifflin office building as they await Hank to fire up the parking lot gate, Toby makes the unfortunate mistake of placing his hand on Pams knee in a random flirtatious gesture.
Normally, this would be awkward enough on its own but the fact that it happens in front of the entire branch issomuch worse.
Scotts Tots (Season 6, Episode 12)
Without a doubt the most difficult episode ofThe Officeto sit through, anyone able to watch Scotts Tots without seizing up in embarrassment needs to see some kind of medical professional.
Quite possibly the most awkward moment inThe Offices history, watching Michael struggling to tell a group of high school kids hes unable to pay for their college education is enough to leave the most hard-hearted viewers gritting their teeth and shaking their head.
Of course, in true Michael Scott fashion, the Dunder Mifflin branch manager somehow manages to make his apology even worse when he meekly tries to substitute college tuition for laptop battery packs, eliciting a chorus of boos from the former Scott Tots program members.
