the office

The Top 5 Cringiest Episodes of TV Sitcom ‘The Office’

Thanks to Michael Scott, things are about to get awkward.
September 9, 2019
9 mins read

The Office” is arguably one of the most popular TV shows in America. Pop culture is rife with references to the classic sitcom; just take one look at Instagram or Twitter and you’ll find thousands of memes from “The Office.” Walk onto a college campus and you’ll see Michael Scott stickers plastered across MacBooks. I mean, if you haven’t watched the show all the way through, three times, then what are you doing with your life?

But as anyone who has seen the iconic show knows, much of the comedy revolves around the cringy escapades of regional manager Michael Scott. His offensive jokes and insensitive manner create some funny scenes, but it also leads to tangibly awkward moments.

Sometimes Scott’s socially inept ways cause the viewer to look away from the screen out of sheer embarrassment. Although this is an extremely difficult endeavor, I will attempt to rank the top 5 cringiest episodes of “The Office.” And trust me, this is going to get awkward.

(All of these episodes can be found on Netflix … for now.)

5. “Phyllis’ Wedding” (Season 3, Episode 15)

A person’s wedding should be the most memorable day of their life, and this is definitely true for Dunder Mifflin saleswoman, Phyllis Vance, but not in a good way. Phyllis’ first mistake was giving Scott a role in the wedding party. She asks him to push her father’s wheelchair down the aisle, secretly hoping that Scott will give her six weeks off for her honeymoon in return.

Imbued with a sense of responsibility, Scott assumes the role of “father of the bride” and commences to upstage the whole ceremony. He haphazardly rolls Phyllis’ father down the aisle, trying to make a scene. Yet her father upstages Scott by miraculously walking the last few steps to his daughter, making Scott boil with anger like a lunatic. Scott then cuts the preacher off by introducing the newly married couple.

At the reception, during the toasts, Scott wrestles away the mic and then proceeds to embarrassingly (for the audience) poke fun at Phyllis’ sexual history. “She looks kinda matronly now, but back in high school her nickname was ‘easy rider,’” Scott proclaims. Phyllis’ husband, Bob Vance (from Vance Refrigeration, of course), promptly kicks him out.

4. “Double Date” (Season 6, Episode 9)

Rule No. 1 of working at an office: Don’t date your coworkers’ relatives. Yet, as usual, Michael Scott has no regard for the rules. To summarize previous episodes, Scott begins dating Pam’s mom, which sends Pam into a rage. In this episode, Jim and Pam finally go on a double date with Scott and her mother, Helene.

Just when Pam is starting to accept her mother’s new relationship, Scott ruins everything. For Helene’s birthday, Scott surprises the group with a lunch, complete with decorations. But, upon learning that Helene is turning 58, Scott starts having second thoughts about the relationship he was just so confident in. This is where Scott’s complete lack of social intelligence comes in: He dumps Helene in the middle of the lunch.

Pam, of course, is furious. When Scott bribes Pam with a pay raise, she counters with getting the opportunity to punch Scott in the face. They meet in the parking lot after work, and although Pam initially shies away, after Scott claims Helene came onto him, she slaps him. It’s enough to make any viewer feel the second-hand embarrassment.


3. “Moroccan Christmas” (Season 5, Episode 11)

As head of the Party Planning Committee, Phyllis plans a Moroccan-themed Christmas celebration. But when you combine alcohol, fire and a tense office environment, you know things are going to get interesting.

As to be expected, Meredith gets drunk and, in the process, she manages to set her hair on fire. Scott attempts to stage an intervention but is ultimately unsuccessful. Instead of leaving well enough alone, Scott basically kidnaps Meredith and tries to force her into rehab. The ensuing struggle between the two is hard to watch.

Unrelated to Scott, the cringiest moment of the episode comes when Phyllis reveals that Angela and Dwight are having an affair. The only person who doesn’t hear the declaration is Andy, Angela’s fiancé. The whole office is forced to keep the secret while Andy remains oblivious.

2. “Dinner Party” (Season 4, Episode 13)

A solid contender for first place, “Dinner Party” is deliciously hilarious, but extremely embarrassing. In this episode, Scott ropes a reluctant Jim and Pam, along with Andy and Angela, into coming over to his condo for a dinner party with his live-in girlfriend, Jan.

The night starts off on the wrong foot with the home tour. After saying the food won’t be done for another three hours, Jan shows them her candle making business and her home office as Scott repeatedly belittles her for being jobless. When showing them the bedroom, it’s obvious that Jan wears the pants in the relationship; she forces Scott to sleep on a tiny bench because of her “space issues.”

The night gets progressively more cringy with the tension escalating at dinner when Jan breaks Scott’s $200 plasma TV with a self-awarded trophy, causing the police to come knocking. The unhealthiness of Scott and Jan’s relationship, and the fact they put it so openly on display, makes for a high-key embarrassing experience.


1. “Scott’s Tots” (Season 6, Episode 12)

We’ve finally arrived at the cringiest episode of “The Office.” In this episode it is revealed that 10 years ago, Scott promised a group of underprivileged kids that he would pay their college tuition if they graduated high school. Well after 10 years, Scott obviously can’t follow through, and he must admit his mistake when the class invites him back for their senior year.

The kids are ecstatic to see Scott, and break out into song: “Hey Mr. Scott, what you gonna do, what you gonna do, make our dreams come true!” It’s enough to make anyone wince uncomfortably.

The kids are then obviously distraught when Scott admits he can’t pay for tuition and he makes it worse by offering them computer batteries to make up for it. One of the kids tells Scott that what he did was “messed up,” which would be anyone’s thought who watched the episode. Dozens of ruined futures make for the cringiest episode, hands down.

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