Top 10 Awkward Moments in The Office US Series

If there’s one thing you don’t do at a wedding, it’s to make it about yourself. Of course, Michael just can’t help himself. After Phyllis says, “I do,” Michael breaks from the groomsmen to loudly announce the marriage, only to be greeted by confused looks and a horribly painful silence. And just when we thought that we couldn’t cringe any harder, the officiant repeats the process to Bob, and not even Michael can handle the embarrassment. Of course, that doesn’t stop him from repeating it AGAIN after Bob says, “I do.” And then he makes a horrific speech, and what was already a terribly weird wedding turns disastrous. This episode is just too much to handle.

Poor Kevin. You just can’t help but feel bad for the poor, pitiful man. In one of the show’s greatest cold opens, Kevin talks about how he spent all night studiously cooking chili for the office, only to drop it all over the floor. It’s a brilliant bit of editing, as Kevin’s panicking and looks of utter desperation are juxtaposed with his prideful boasting. Of course, the show has to take the scene one step further, and Kevin starts slipping in the spilled chili. He’s just so pathetic it hurts. Forget Jim saying goodbye to Michael or Pam crying over her broken dreams – this is the saddest moment in “The Office.”

We’re glad they toned down Michael’s obnoxiousness for Season 2, because Season 1 Michael is just unbearable. Take, for example, the entire “Diversity Day” episode. The whole thing was an absolutely horrible idea, but it culminates in one of Michael’s most punchable moments. Once Kelly shows up from a meeting, Michael approaches her and begins a terribly racist tirade that leaves Kelly, and the rest of the office, in utter shock and disbelief. We watch as Kelly’s face goes from happy to furious, and it culminates in a totally warranted slap to the face. Even if you adore Michael, you have to admit that he was a total SOB here.

And here we see Meredith go from sexually promiscuous to full-on harassing. It’s… a little awkward, to say the least. Meredith’s fractured pelvis leaves her with a crotch cast, and naturally, she wants Jim to sign it. And of course, Jim is too nice to say no. John Krasinski is fantastic in this scene, as he naturally, and hilariously, switches from openly polite to politely uncomfortable once Jim realizes what Meredith wants. And once the painful deed is finished, he looks utterly shell-shocked, clearly disturbed with what he has just been put through. When it comes to reacting to uncomfortable situations, John Krasinski has no equal.

Season 3’s “Gay Witch Hunt” is arguably one of the most unbearable episodes of “The Office.” It’s up there with “Phyllis’ Wedding” and “Diversity Day,” that’s for sure. After using a derogatory term and accidentally outing Oscar to the office, Michael hosts a… um, seminar, we guess you could call it… on homosexuality. And to make Oscar feel welcomed, Michael kisses him on the lips. Yeeeah. While his intentions were good, the kiss was wildly inappropriate, and it only makes the dicey situation that much worse. This scene also proves that Steve Carell had a firm grasp on his character, as the kiss was totally improvised. You can even tell by Oscar’s legitimately surprised reaction. Good on him for staying in character, though.

Michael’s infatuation with Carol is one of the show’s most wince-inducing storylines, and it provided some of the most gloriously uneasy scenes in the show’s history. Like this complete abomination of a proposal! Not only does Michael interrupt the Diwali celebration, he also refers to himself as a “gringo” and singles out Carol, who is inappropriately dressed as a cheerleader (thanks to Michael). It’s problematic enough before the actual proposal, and the whole thing is just a recipe for disaster. The tension explodes when Michael proposes, as Carol rejects him by wishing to talk in private and storming off in embarrassment. Rejected public proposals are always painful to watch, and even though this is fiction, we can’t help ourselves from cringing in discomfort.

Forget Carol – Michael’s entire dating life pre-Holly was just one giant mess. For example, he knowingly dated Pam’s mother and then broke up with her during her own birthday lunch. That understandably caused some friction in the office. But perhaps the most horrible, and funniest, dating snafu comes in season four’s “Chair Model.” Pam sets Michael up on a blind date with her landlady, and Michael obviously expects a 10/10 bombshell. But when Michael spots his homely date, he grows visibly distraught and even feigns total ignorance when she approaches. Funnily enough, it actually seems to work… until the barista blows it up in Michael’s face. The following fifteen seconds of silence are pure torture, and we love it. It’s delectable “Office” cringe.

Alright viewers, be warned. We have left the humor behind and have now entered into the excruciating part of the list. And what better way to start that off than Toby affectionately touching Pam’s leg? Everything about this scene makes us squirm, from the way the camera zooms into Toby’s hand to everyone’s looks of total disbelief to the unpleasant silence following the action. The situation is so awkward that Toby literally runs away, and really, we would too if we could. It’s moments like this that make us both love and hate “The Office” – we love it because it’s so deliriously cringe-worthy and funny, but we hate it because it physically hurts to watch.

Michael and Jan’s dinner party is the stuff of nightmares. Jim, Pam, Andy, and Angela all go over to Michael’s place for dinner, and what results is the most agonizing twenty minutes ever put on television. Things start off weird, as we see their ridiculous sleeping arrangements, sex camera, and Michael’s hilariously small TV, which he is forced to stand in front of. But then things go off the rails with Jan’s intimate song, Michael’s attempt at scamming Jim and Andy, and Jan destroying Michael’s $200 TV. It’s said that the actors had a difficult time filming this episode, and we can see why. It’s absolutely hilarious, but it’s probably one of the hardest things we’ve ever had to watch.

Before we recoil from our top pick, here are a few honorable mentions.

Pushing Tony Onto the Table
“The Merger”

Andy Dates a High Schooler
"Product Recall"

Toby Can’t Go to the Beach
"Beach Games"

Holly Thinks Kevin Is Mentally Disabled
"Goodbye, Toby"

Jan’s Baby Shower
"Baby Shower"

We don’t think it’s possible to watch “Scott’s Tots” all the way through. It’s just a little too much. Ten years earlier, Michael promised a group of underprivileged children that he would pay for their college tuition if they graduated high school. Now is the time to make good on the promise, and Michael doesn’t have the money. Cue the unbearable tension as Michael finds a way to break the news to the elated teenagers. To make matters worse, he offers an appeasement… with laptop batteries. And with that, we’re out. We can’t watch anymore. This episode ventures into full-on unpleasantness, and we challenge anyone to watch it without looking through their fingers. It’s a masterpiece of cringe comedy.