The 7 Cringiest Moments of The Office, Ranked

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 Office continuously drew on a distinct idiosyncratic sense of humor that mainstream audiences instantly fell in love with. However, it’s also no secret that The Office’s showrunners occasionally went a bit too far in their comedic subject matter, inducing as many groans of embarrassment as it did avid laughter from viewers.

From awkward wedding ceremonies to uncomfortable dinner parties, here are some of the cringiest moments in The Office, ranked from humiliating to practically unwatchable. 

Michael Nearly Derails Phyllis’s 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 Phyllis’s 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 Vance’s groomsmen. If that weren’t bad enough, he then proceeds to unsuccessfully steal the spotlight once again by proclaiming Phyllis and Bob Vance as officially married – before the minister can declare them an official couple. Talk about going from bad to worse… 

Michael’s Botched Marriage Proposal (Season 3, Episode 6)

Say what you will about Michael’s antics in the earliest seasons of The Office, but no one deserves the treatment he received in season 3’s “Diwali.” Caught up in the festivities of Kelly’s 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)

What’s worse than having your significant other shoot down your marriage proposal in front of your coworkers and a bunch of strangers? Hmm, it’s difficult to say, but we’ll 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 “Diwali”’s cringe-inducing runtime.

Jim and Pam’s Dojo Disaster (Season 2, Episode 6)

Sure, Jim and Pam had plenty of adorable moments flirting with each other throughout The Office, but season two’s “The Fight” is definitely not one of them. As they await Dwight and Michael’s karate showdown in Dwight’s dojo, Jim and Pam get a bit physical on their own, leading to Jim accidentally exposing some of Pam’s midriff in front of her coworkers (much to Pam’s 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 Pam’s relationship absolutely mortified.

Michael and Jan Ruin Their Dinner Party (Season 4, Episode 13)

Say what you will about “Scott’s Tots,” but at least that now infamous scene doesn’t span an entire episode. The moment Jim and Pam arrive at Michael’s humble abode in “Dinner Party,” however, viewers can’t help but instinctively start to tense up from sheer discomfort. Of course, it doesn’t 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 it’s called ‘Let’s See How Uncomfortable We Can Make Our Guests?’” Watching the finished episode – including Michael and Jan’s awkward house tour and their full-blown shouting match over dinner – it’s hard to argue against Jim’s highly accurate assessment.

Toby Touches Pam’s Leg (Season 4, Episode 15)

Ironically, one of the most painful moments of The Office doesn’t 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 open the parking lot gate, Toby makes the unfortunate mistake of placing his hand on Pam’s 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 is so much worse.

Scott’s Tots (Season 6, Episode 12)

Without a doubt the most difficult episode of The Office to sit through, anyone able to watch “Scott’s Tots” without seizing up in embarrassment needs to see some kind of medical professional. Quite possibly the most awkward moment in The Office’s history, watching Michael struggling to tell a group of high school kids he’s 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.