10 Most Cringe-Worthy ‘The Office’ Moments

Cringe-alert!!! Hey folks, as we know, “The Office” is one of the most-watched and loved sitcoms of all time. And if you have watched the show, you know it very well that this mockumentary sitcom is packed with a lot of cringe humor. So much so that cringe often becomes a necessity for the show to be funny and comedic.

It would not be wrong to say that ‘The Office’ is one of the best shows that makes us love to cringe humor, and it portrayed it so well on our televisions for years and years. And we must admit, it got better year after year. So keeping that in mind, we thought why don’t we compile a list of the most cringe-worthy ‘The Office’ moments.

Here are the 10 most cringe-worthy ‘The Office’ moments. So let’s start.

10. Michael announcing Bob and Phyllis’ marriage and the toast

Bob and Phyllis’s wedding was one of the most awkward moments of ‘The office’. Phyllis’ stealing Pam’s ideas for her wedding was too hard to watch. But to make matters worse, we saw Michael announcing Bob and Phyllis’ wedding even before Bob said “I do”. And to make things even more uncomfortable, Michael also gave an awkward toast which wasn’t at all necessary. And this became one of the most hilariously awkward moments of the show, which will make you awkward every time you watch it.

9. Kevin dropping his chilies

We all love Kevin’s smile after saying almost everything on the camera but when we all felt sorry when Kevin spilled his chilies in the ‘Casual Friday’ episode. On top of that, Kevin slipping on the spilled chilies made it even more memorable. And knowing the fact that he spent the whole night making this for his friends makes us even more sorry. It definitely is one of the hilariously portrayed uncomfortable scenes of ‘The Office’, making anyone feel cringe.

8. Toby touching Pam’s legs

Toby’s attraction towards Pam was in itself one of the most awkward things for the office. But to top that, when everyone was locked in the office, Toby affectionately touched Pam’s knee as if he was in a relationship with her. This was so hard to watch, not only for fans but for the office employees as well that Toby left the place as soon as possible which made the scene, even more, cringe-worthy.

7. Michael’s Indian character on diversity day

It is Michael’s habit to making fun of almost everything but sometimes it becomes very serious that it becomes too hard to handle. One such instance was when Michael talked in a weird Indian accent to Kelly on ‘Diversity Day’. Though the scene started as a hilarious one, it made Kelly very embarrassed and she ended up slapping Michael. Maybe we would have done the same!

6. Jim signing Meredith’s crotch cast

This is one of the most problematic scenes of ‘The Office’. If you just watch this scene carefully, you will see how awkward Jim felt when Meredith asked him to sign her crotch cast. Oh my God! It was too hard for anyone to watch that and not feel awkward. And above all, Jim’s facial expression after signing the cast was the best expression ever. So now let’s see what are the top 5 most cringe-worthy ‘The Office’ moments.

5. Michael and Oscar’s kiss at Diversity day

‘Diversity Day’ episode is stuffed with the most awkward moments and the one we have here was actually an improvisation by the actor Steve Carell. While telling other how they should be open to people of all cultures and orientation, Michael very awkwardly kisses Oscar. Oscar on the other side does everything to stop but couldn’t do so. This scene is funny and embarrassing all at the same time.

4. Michael’s blind date in the Model chair

When Michael felt sad because of the death of the model he saw in an ad post, Pam fixed him a blind date. But to Pam’s horror, Michael didn’t like her face and pretended he wasn’t the Michael she was asking for. This scene is again packed with cringe-content and it also makes you hate Michael but surely one of the scenes you can’t see without getting a little bit embarrassed.

3. Holly thinks Kevin is mentally-challenged

Holly was very much like Michael when it came to being funny, but one of the things that were indigestible and made us very uncomfortable was the fact that she really believed that Kevin was mentally challenged. Though we did love her caring, sweet attitude towards him as a whole this made many cringe hard just like Kevin and other office members.

2. Michael and Jan’s dinner party

Before Holly, all the romantic relationships of Michael were a mess. But his relationship with Jan was very weird and often left us shocked. And one of the embarrassing moments of their relationship was the dinner party they hosted for Andy, Angela, Pam, and Jim. To everyone’s horror, Jan and Michael started attacking each other first through words and eventually physically. This not only made the party members cringe but made all of them cringe as well.

1. Scott’s Tots

For anyone who has seen ‘The Office’ knows that Michael is not a bad person at heart and it appears in many things, he does for others. But one of the most cringe-worthy moments was him telling the students of Scott’s tots that he will not be able to pay for their studies. Fans find it hard to watch the episode without pausing it in between. The moment is so packed with cringe, awkwardness, and embarrassment that you cannot help but watch it through your fingers.

There are so much more cringe-worthy moments in ‘The Office’ but this was our list of top 10 most cringe-worthy ‘The Office’ moments. Let us know your thoughts about it and your most cringe-worthy ‘The Office’ moments in the comment section below. Thanks for reading.

Checkout: The Hardest ‘The Office’ Quiz