When you think of The Office, the first words that come to mind are probably “hilarious” and maybe even “heartfelt.” But shortly behind are definitely “awkward” and “cringeworthy,” thanks to the many uncomfortable moments Michael Scott and the entire Dunder Mifflin gang get themselves into on an episode basis.
From Michael promising to pay for students’ college tuitions, to Ryan being pressured to propose to Kelly by her parents, there are tons of cringeworthy episodes in the NBC show’s amazing nine-season run. Here are 10 of the best ones that’ll make you cover your eyes with discomfort.
Taking the top spot for the most cringeworthy episode ever comes during season 6, when Michael is reminded that it’s been 10 years since he promised elementary school students he would pay for their college tuition if they graduated high school. Obviously, Michael does not have the funds to do such a thing, and instead shows up to the class only being able to buy them computer batteries. It hurts my soul just thinking about those poor kids.
My personal favorite episode of The Office also happens to be one of the most awkward. The season 4 episode “Dinner Party” sees Michael and his girlfriend Jan hosting a dinner for four of Michael’s co-workers (and a couple of self-inviters). Viewers get to see Jan turn from a bit quirky to absolutely insane, as well as Michael attempting to deal with the situation. It’s TV gold.
The season 8 episode “Garden Party” is essentially all about Andy’s rejection by his family, and yes, it gets kind of dark. When he decides to throw a party at Schrute Farms to impress his parents, things don’t exactly go as planned. Andy is publicly embarrassed by his dad and his brother, which leaves him defeated.
If someone asked me which episode of The Office fully wouldn’t work in today’s climate, I’d have to pick “Diversity Day” from season 1. Though Michael has good intentions (I think?) in trying to educate his employees on the importance of inclusivity and diversity, his plans go horribly wrong when he challenges the office to highlight and embrace offensive stereotypes.
There’s no Dunder Mifflin wedding without Michael, as he’s proved plenty of times over. When Phyllis marries Bob in season 3, tension begins after Pam realizes her co-worker had copied her exact designs for her planned wedding to her ex, Roy, and things escalate when Michael tries to take on the “father of the bride” role. Yeah, ew.
Going on a double date with one of your parents and their new significant other must be strange, but what happens when their object of affection is your boss? That’s exactly what happens to Pam in season 6, when Michael starts dating her mom, Helene. To make matters worse, when they go out to eat for Helene’s birthday, Michael finds out her age and quickly breaks up with her right then and there. Ouch.
Another terribly awkward moment from Michael comes during season 7, when his nephew Luke is hired as the new office assistant. It soon becomes evident that he new kid is not exactly the best worker, and the Dunder Mifflin employees want him out. But instead of firing or even lecturing him, Michael repeatedly spanks Luke in front of the office in a weird display.
The season 3 episode “Diwali” is full of awkward moments, but the best scene of all has to be when Michael proposes to his girlfriend Carol in front of the entire Diwali celebration, all while she’s wearing a cheerleader uniform (Michael had wrongfully informed her they were going to a costume party). Clearly, the gathering is a culture shock for many of the Dunder Mifflin employees.
Every Christmas episode on The Office is special in its own way, but season 6 definitely brings the most cringeworthy. This episode shows Michael upset and angry that the office allowed Phyllis to take on the role of Santa, which leads to him deciding to dress up as Jesus. Things get even worse when Michael is alerted that the company might be sold, and he almost immediately tells his employees that they’ll likely be losing their jobs.
Though the season 5 episode “Company Picnic” might be one of the cutest ever because of Jim and Pam finding out they’re expecting their first child, it’s also one of the most uncomfortable. Why? Well, because of Michael, of course. Amidst him trying to win Holly back, he also casually announces to the whole company that one of the branches will be closing, marking the first time they’re hearing the news.