25. When Pam got Jim into the Finer Things Club and then he didn't even read the book.
Season 4, Episode 6: "Branch Wars"
Just read the book, dude! Come on! Other people (Andy) have been waiting for the day they get called in to join the best club at the Dunder Mifflin Scranton branch, and you’re just making jokes.
24. When Michael promised Bruce Springsteen tickets for the Crime Aid auction but never actually had any tickets.
Season 5, Episode 5: "Crime Aid"
Let's be honest, did anyone really think Michael bought tickets to see The Boss? Does that sound like something Michael would do?
23. When Michael tried to make good with Phyllis but took it too far.
Season 2, Episode 2: "Sexual Harassment"
Michael had the situation all settled. He was GOOD. Phyllis was happy, laughing, and appreciated Michael sticking up for her after Packer made a joke... but then it happened. Like a million times before and a million times after, Michael took it too far.
22. When Michael was set up on a blind date by Pam, saw the woman he was supposed to go on a date with, and then pretended not to be himself because he didn't like her face.
Season 4, Episode 10: "The Chair Model"
You can see the pain on her face as she tries to make the best of this god-awful situation. You'd think Pam and Jim would learn not to set Michael up on dates with people they know but...
21. When "Date Mike" was asked to leave the bar by the manager.
Season 6, Episode 21: "Happy Hour"
Michael was all fine and dandy until he realized Pam and Jim set him up on a date. Date Mike took it too far after trying to imitate "dating experts" he saw on TV... then continued to take it farther. May Date Mike never resurface again.
20. When Andy's phone went off while he was on stage during his play.
Season 7, Episode 3: "Andy's Play"
To all of us watching, this is fairly hard to watch. To anyone who has ever participated in local musical theatre, this is unbearable.
19. When Michael brought in the owner of the building and tried to act like him clamping his foot in a grill is like being in a wheelchair.
Season 2, Episode 12: "The Injury"
If we've learned anything from this cringy moment, it's that Michael brushes his teeth for only 10 seconds.
18. When Michael broke up with Pam's mother ON her birthday.
Season 6, Episode 9: "Double Date"
Some advice for anyone reading this, don't date your friend's or coworker's mothers. Maybe that didn't need to be said, but just in case.
17. When Darryl tried to gain sympathy by having his daughter talk him up and it went very wrong.
Season 7, episode 26: "Search Committee: Part 2"
This is a historical moment on The Office, as it is one of only a few moments where a character messes up, realizes it, and immediately aborts the plan.
16. When Andy pretended to be down on his luck even though he knew David Wallace would be making him manager.
Season 8, Episode 24: "Free Family Portrait Studio"
NEVER. TRY. TO. FORCE. A. MOMENT. If you didn't know that by now, Andy proves it here as he tries to force a "started from the bottom now we here" situation.
15. When Michael prematurely announced Phyllis and Bob as a married couple before Bob had said "I do."
Season 3, Episode 15: "Phyllis' Wedding"
1. Michael wasn't suppose to even be up there. 2. This was after he dragged a wheelchair down the aisle loudly. 3. He yelled loudly in a church so his interruption echoed off the walls 'til the end of time.
14. And later that same night, when Michael gave an unwanted toast.
Season 3, Episode 15: "Phyllis' Wedding"
The look on Bob's face, OMG. I swore this was the moment when Michael would finally get punched in the nose.
13. When Jim defaced a photo of his own daughter to try and get Dwight in trouble for it, but it backfired quickly.
Season 8, Episode 10: "Christmas Wishes"
Jim may be a dick sometimes, but he isn't going to get Dwight fired over a prank. Too bad, because it really would have helped him get out of this awkward jam if he just let Dwight falsely be accused of drawing devil horns on a photo of Cece.
12. When Toby touched Pam's leg.
Season 4, Episode 11: "Night Out"
Get your grimy hands off Pam's leg! No one wants you to touch them! This is the moment you finally understood why everyone hates Toby so much.
11. When Cathy wouldn't leave Jim's hotel room and kept making advances on Pam's husband.
Season 8, Episode 16: "After Hours"
You want to mess with Jimmy Halpert, Cathy? Then you will have to face the wrath of a one Mr. Dwight K. Schrute! Even if Dwight doesn't realize he's helping.
10. When Michael and Dwight tried to push Tony up onto the table.
Season 3, Episode 8: "The Merger"
This moment seemed like it was never ending. How many times does someone have to say "stop" before you stop?!? Ugh, Tony is better off not staying at the Scranton branch.
9. When Michael ruined Holly's Woody doll, then was confronted about it.
Season 7, Episode 12: "Classy Christmas: Part 2"
If anyone out there has a crush on someone, may I politely suggest you don't ruin their personal belongings and tell them you want to have children with them.
8. When Michael tried to forcibly hug Oscar but Oscar didn't want to be hugged. Then, after lashing out at Michael, Oscar endured being kissed.
Season 3, Episode 1: "Gay Witch Hunt"
This moment did give Oscar some paid vacation time, but was it really worth it?
7. The "Dinner Party" episode as a whole.
Season 4, Episode 9: "Dinner Party"
This episode was an uncomfortable roller coaster ride from start to finish! If the end wasn't saved by a cute Pam and Jim moment then ohhhh boy, this would have left me in a fetal position after watching it.
My face during the whole "Dinner Party" episode.
6. When Michael proposed to Carol at Diwali.
Season 3, Episode 6: "Diwali"
OMG! You know that feeling when you make a joke and someone barely hears it and asks you to repeat it? But by the time you repeat it, the moment has passed and there is just this lingering awkwardness? Well this moment is that times infinity.
5. When Holly mistook Kevin for being mentally disabled thanks to Dwight.
Season 5, Episode 1: "Weight Loss: Part 1"
This moment is extra hard as Holly was only doing what she thought was right, but was on the wrong end of a prank by Dwight.
4. When Michael fake fired Pam and it wasn't as funny as he hoped.
Season, Episode 1: "Pilot"
You'd think Michael would learn from this moment and not just repeat it again in season 5, but then again, there are a lot of things Michael shouldn't do that he ends up doing.
3. When Michael showed the clip of him on Fundle Bundle in which we get a glimpse of how lonely he has been his whole life.
Season 2, Episode 18: "Take Your Daughter to Work Day"
The one benefit of having children is you can force them to be your friend and they can't do ANYTHING ABOUT IT.
2. When Kevin spilled his homemade chili he spent hours making.
Season 5, Episode 26: "Casual Friday"
Oh Kevin. This is one of those moments where if this happened to me I feel like I'd just quit, never to return again. Actually, that is how I feel when I watch this moment.
1. And finally, Scott's Tots... do I really need to say much more?
Season 6, Episode 12: "Scott's Tots"
Similar to a horror movie when the music gets more dramatic as the killer gets closer, the episode built to Michael breaking the news he can't pay for anyone's college in the most tense way possible. The whole time Michael made his speech to the class, I hid my face in my shirt because I just can't bare to watch!
