32 Times Characters On The Office Made A Bad Choice

The Office is one of television’s best comedies, and a lot of this is due to the hilarious times characters in the show messed up. Michael Scott is certainly the gold standard for characters who made epic blunders, but most everyone at the Dunder Mifflin Scranton Branch is guilty of at least one major error.

After revisiting a number of episodes with my Peacock Premium subscription, I believe I’ve whittled down a list of 30+ different moments a character on The Office messed up. Surprisingly, none of these moments are Dwight falling for one of Jim’s pranks, which really says something about how wild things got on the sitcom.

Michael Grilling His Foot Making Bacon

Loving to wake up to the smell of bacon in the morning is not worth a potential burn on your foot, though Michael Scott said otherwise in “The Injury.” Planting his foot on a George Foreman grill next to his bed might be one of the most memorable Michael blunders of all time.

 

Eating Todd Packer’s Cupcakes

Todd Packer was perhaps one of the shadiest characters of The Office, and while we didn’t need any evidence by the time he was finally fired in “The Farm”, his final act really drove the point home. Packer offered cupcakes to the staff before leaving, only to later reveal on camera that he laced the cupcakes with drugs that had a variety of affects on those who ate them.

 

Roy Attacks Jim At Work

Roy’s attempt to win back Pam was a rough arc to watch, but it came to an upsetting end in “The Negotiation” when he rushed Jim at the Dunder Mifflin office and tried to attack him. He was thwarted by Dwight, who pepper-sprayed him. Roy was fired later, and it effectively ended whatever small chance he had at salvaging his relationship with Pam.

Dwight Does A Realistic Fire Drill

“Stress Relief” features the most hilarious and preventable screw-up of The Office, when Dwight decided to stage a fire drill that involved actual fire, among other traps. Stanley ended up having a heart attack because of the ordeal, so it’s hard not to look back on this one as one of the bigger times someone messed up.

Michael Dating Jan

If there were an award for the most toxic relationship in television sitcom history, I think Michael and Jan would have to be in top contention to win. There was always a question of whether or not Jan loved Michael for who he was, or because he was around at a rough time in her life. We could debate that all day, but between the memories of the awkward dinner party to her surprise pregnancy, I think we can agree both would’ve been better off not dating.

 

Michael Starts Scott’s Tots

“Scott’s Tots” is infamous for The Office fans, and is the top-ranked cringe-worthy episode on CinemaBlend. Michael had to face the empty promise he made to a bunch of underprivileged children to fund their college education in an absolutely brutal episode of television. Just writing about it makes me feel ill.

Andy Accidentally Dates A Highschooler

Andy Bernard made a lot of mistakes when it came to love on The Office, but perhaps one of his biggest missteps came in “Product Recall” when he happened upon his girlfriend while visiting a high school on business with Jim. Fortunately, his relationship with the part-time frozen yogurt chef never went too far, minus the fact they knocked over a mailbox with her friends.

The Yankee Swap Decision

“Christmas Party” is surely on many people’s list of the best Christmas episodes of The Office, but it’s also top of the list for someone messing up. Michael messed up by buying the video iPod that far-exceeded the $20 limit for Secret Santa. Jim messed up by giving Pam a gift that might’ve been a touch too personal, and Phyllis messed up by thinking Michael would want that oven mitt. Let’s not forget Kelly also kissed Dwight, which I’m sure she also regretted.

Phyllis Letting Michael Be A Part Of Her Wedding

While it all worked out for the better in “Phyllis’ Wedding,” I’ll never for the life of me understand why Phyllis asked Michael to have any role in her wedding. Sure, he found Uncle Al (unintentionally), and made a happy day less stressful, but does that really make up for the outbursts during the ceremony, or the crude remarks during the wedding toast? I’d say no, and I’d reckon Bob Vance from Vance Refrigeration would say the same.

Angela Agreeing To Let A Duel Decide Who She’ll Stay With

Angela’s affair with Dwight led to him having a duel with Andy, but it was completely unnecessary. The smart decision would’ve been for her to just leave Andy for Dwight, as that was where her true affections were. Instead, she allowed them to fight and both men discovered she betrayed them in various ways. By the end she had neither, so it’s hard to argue this wasn’t a mistake on her end.

Deangelo Hospitalized Dunking A Basketball

Deangelo Vickers had a short run as the branch manager at Dunder Mifflin. This was due to his decision in “The Inner Circle” to try and dunk a basketball to inspire the staff, which ended up collapsing the hoop. Deangelo was rushed to the hospital and despite a brief return wrapped in bandages, was left comatose. It’s later stated that Vickers is brain dead as a result of the incident, which remains one of the roughest exits for a character on the show.

David Wallace Transferring Holly to Nashua

After witnessing them kissing in “Crime Aid,” David Wallace made the decision to transfer Holly away from Scranton, to Nashua. The move ended up putting a big wedge between David and Michael, and would only cause further tension between them down the line.

Kevin Should’ve Gotten Tupperware To Secure His Chili

The iconic chili cold-open in “Casual Friday” has driven me up a wall for years. Why did Kevin bring his chili to the office in the pot he cooked it in? Why would he not have used some kind of sealable container? If he had, perhaps actor Brian Baumgartner wouldn’t have been caked with the smell of chili, which is just one of the interesting facts from The Office fans may not know.

Jim Shouldn’t Have Accepted Dwight’s Challenge To A Snowball Fight

Jim gets the better of Dwight 90% of the time they feud, but he should’ve known something like a snowball fight wasn’t his bag. With no prep time, he strolled out to have a snowball fight, only to get obliterated by an overly prepared Dwight. It was nice to see Dwight get a win for once!

Michael Shouldn’t Have Carbo Loaded Before The Rabies Awareness Race

It’s one thing to refuse water during a rabies awareness race, and it’s quite another to “carbo load” on fettuccine alfredo moments before running. Michael Scott did both in “Fun Run,” and ended up in the hospital as a result. He did earn Meredith’s forgiveness though, so that’s something.

Stanley Shouldn’t Have Yelled At Michael

“Did I Stutter?” is a line so iconic in The Office that it’s the title of the episode. If only Stanley had remained calm and collected as he often is and not shouted at Michael during the meeting, he could’ve avoided a lot of headache trying to explain to his boss why he doesn’t respect him. It all ultimately worked out, but I doubt the crossword puzzle was finished during work hours that day.

Michael Shouldn’t Have Listened To His GPS

The unfortunate blunder in “Dunder Mifflin Infinity” is so on point with the rest of the episode, one can’t help but laugh. Only Michael Scott would set out to prove that being tech savvy isn’t the key to a flourishing business, only to be rejected by former clients complaining about their bad website. Michael then crashing a rental car into a lake because he was listening to his GPS is the perfect exclamation point that drives the joke home oh so perfectly.

 

Darryl Shouldn’t Have Listened To Kelly’s Subtext Texting Notes

Darryl deserves a reckoning for hitting on a woman in a committed relationship the same as Jim does Pam, though he was far less sneaky. Allowing Kelly to analyze the dots in the text in “After Hours” helped Val’s boyfriend Brandon realize something was up, which made for some awkward moments between them.