19 Moments From "The Office" So Awkward You Might Have Skipped These Episodes Entirely

19 Moments From "The Office" So Awkward You Might Have Skipped These Episodes Entirely

The Office is a masterclass of cringe, but that isn't always a good thing.

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This classic workplace sitcom has many cringe-inducing moments that even the most diehard fans have trouble watching. Since we're visiting Dunder Mifflin once again, let's go through the most awkward moments from The Office.


19. Enter Date Mike

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The situation here is that Jim and Pam set Michael up on a date without him knowing. Though he and his date have a good time with him just being himself, Michael eventually learns the truth and ends up dropping the ball. He does this by transforming into Date Mike, his idea of a cool and wild guy that gets all the ladies. He does not, and everyone knows why.

18. The Dinner Party

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Jim and Pam are invited to a dinner party and Michael and Jan's condo, and it's just a full half-hour of weapons-grade cringe. The party hosts slowly lose their minds as they get at each other's throats, and many uncomfortable truths come to light. These include Dwight dating his old babysitter and Jan being attracted to her former teen intern. All in all, this episode is a classic, but it's still a challenge to get through.

17. Stamford Orientation

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When Michael's branch absorbs this closed Stamford branch, he introduces them to life in Scranton in the most uncomfortable way possible. He acts so inconsiderately ridiculous towards them, it's no wonder that most of them didn't stay long. Part of us wishes we could work at this wacky paper company, but the Stamford people's experience on their first day is basically what it would be like if someone actually joined an office like this in real life.

16. Andy Breaks Up With Jessica

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After Andy gets back together with Erin in Florida, they both drive to a bachelorette party that his girlfriend, Jessica, is at. She was a wonderful woman for him, so it was hard to watch him dump her the way he did. However, having lied to her about his reason for their breakup, he ends going to see her AGAIN to tell the truth, but it doesn't make it any better. 

15. Pam Tells Roy the Truth

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We were all rooting for Pam to start dating Jim, but it was still hard to see her tell Roy about their kiss. He is understandably upset, but he takes it a step too far and wrecks the bar they're sitting at in a blind rage. The man edges toward assault in this scene, making it even harder to believe Pam stayed with him for so long.

14. Michael's Casino Date(s)

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In the Season 2 finale, Michael accidentally gets two dates with Carol and Jan for his branch's casino night. We've all seen this sitcom trope at least once, but since all of them are fully aware of the dilemma, this makes this classic episode somewhat difficult to watch. Jan isn't the character everybody routes for, but seeing how mad and uncomfortable she is is enough to make you uncomfortable too.

13. Toby Touches Pam's Knee

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Jim's face in this one says it all. When the office gets their cars trapped in the parking lot, Toby tells a joke and ends up making a pass at Pam. Everyone is clearly thrown off by this, and so Toby reveals he's leaving for Costa Rica before literally hopping the fence and running away. It's this kind of creepy behavior that makes us think that Toby is the Scranton Strangler. #tobyisthescrantonstrangler

12. Andy's Revenge

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To say that Andy was a jerk to Erin in Season 9 is an understatement. He neglected her, left on a months-long boat trip without her, and still had the audacity to seek payback after she broke up with him. To get back at her and Pete for dating behind his back, Andy brings their exes to the office and watches with glee as they fight. It's an uncomfortable episode to watch, especially since Andy didn't quite get any comeuppance for his jerkish behavior towards her.

11. Michael Dates Pam's Landlady

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After Michael's inglorious breakup with Jan, Pam sets him up on a blind date with her landlord. Though Pam claims she is "sweet," Michael gets put off by her appearance. After trying to pretend he isn't her date, he spends their whole date being a jerk and talking about how much prettier Jan is. It's a miracle Pam wasn't kicked out of her apartment after this disastrous date.

10. Michael at Phyllis's Wedding

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On what was supposed to be a completely happy day, Michael wheels Phyllis's father down the aisle, only for him to walk the last few steps. Feeling the spotlight was taken from him, Michael attempts to get it back. This culminates in a long-winded and embarrassing wedding toast that gets him booted from the celebration. Michael has always had a compulsive need for attention, but seeing him get in the way of Phyllis's day is just hard to watch.

9. Andy Gets Upset Over A Cappella

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In the hopes of mentoring the successors of his college a cappella group, Andy invites them, to sing at the office. However, he becomes frustrated when they claim that his old friend, Broccoli Rob, was called "The Boner Champ." It's hard to watch Andy in this scene, you could tell that those college kids are just aching to leave, praying he doesn't kill them. It was Halloween, after all.

8. Pam and Dwight Reunite With Jan

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This was a reunion these two hoped they never had to endure. When the two of them go on a sales call together, they are horrified to learn that their client is their old superior, Jan. Dwight understandably leaves, forcing Pam to suffer through an agonizing meeting with her volatile client, praying she doesn't make her angry.

7. Michael Ruins Holly's Christmas

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When Michael's true love, Holly, returns to Scranton, Michael decides to throw a fancy Christmas party for her in the hopes of getting back together with her. However, when he finds out that she is still dating her boyfriend, A.J., Michael defaces her favorite Woody doll and tries to brush it off as a joke when she finds out. It's still hard to believe she married him after that.

6. Michael Proposes to Carol

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Michael really jumped the gun on this one. When Kelly invites the office to her Diwali celebration, Michael decides to get up on stage and propose to his girlfriend, Carol. Since they've only gone out on nine dates, Carol understandably leaves the room. And this scene leads me to the next entry on this list.

5. Michael Tries To Kiss Pam

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After Michael is left saddened by his failed marriage proposal, Pam sits outside with him to provide some comfort. However, Michael misinterprets this and tries to kiss her, making the night much worse than it already was. Michael has always yearned for human intimacy, but he just doesn't know how to read a room.

4. Michael Cries at Holly's Office

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When Michael visits Holly's new office, he learns that she is now dating another man. This leaves Michael's heart shattered, and he breaks down crying in his presentation to the branch. He was just lucky Holly didn't have to see them like this, because it is just painful to witness.

3. Jim and Pam Fight

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This was the lowest point in the duo's marriage. After Pam fails to film her daughter's dance recital for Jim, the latter yells at her over it. In response, Pam lets out all her pent-up frustration over him taking his new job behind her back. After Jim angrily hangs up, Pam cries to the point that she needs one of the documentary's crewmen to comfort her. It's a truly upsetting and uncomfortable way to end an episode.

2. Michael Dumps Pam's Mom

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Michael has had some pretty nasty breakups, but this was a new low. After throwing a wonderful birthday party for Pam's mom, whom he's been dating, Michael decides to break up with her after learning she's 58 (even though he's around the same age). He immediately goes from a loving boyfriend to a judgmental jerk, and him slowly ending their relationship is like watching a fish die on dry land.

1. Scott's Tots

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This was a huge Band-Aid Michael had to rip off. In this infamous episode, Michael remembered promising to pay an entire class's college tuition out of his delusional belief that he would be rich by then. He then has to sit and watch them all dance for him, knowing he has to tell them the truth and shatter their dreams. And watching him actually do it is just as painful. It's baffling that some people actually considered this episode one of the best in the series. Meanwhile, the rest of us happily skip it whenever it shows up.

Do you agree with this list? Were there any other awkward Office moments we missed? Please let us know in the comments section below.