The Office has its fair share of reoccurring gags throughout the series' nine seasons but the one that never gets old is the relationship between Michael Scott and Toby Flenderson. Due to Toby being an HR rep, Michael didn't refer to him as a member of the Dunder Mifflin Scranton family. He saw Toby as a member of corporate — someone who was trying to suck the fun out of everything Michael planned. In reality, Toby was a standup guy who got along with everyone in the office. It was his logical and ethical mindset that made him Michael's enemy.
Before Michael's departure in the seventh season, he and Toby had plenty of uncomfortable moments; moments that made viewers feel horrible for Toby. As the HR rep, he didn't really have anyone to complain to and Michael took advantage of that (comically, of course). And while it's been seven years since the series ended, let's take a look at 10 hilariously uncomfortable moments between Michael and Toby.
When Michael Tells Purse Girl That Toby Doesn't Have A Family
In the episode "Hot Girl," Dunder Mifflin hoping to sell some purses to the offices in the building. Seeing how attractive Katy was, Michael goes above and beyond to make her comfortable and gives her a place to set up in the conference room.
He introduces her to the office and when he gets to Toby, Michael butchers any chance Toby may have had at a chance with Katy. He immediately tells her that Toby is recently divorced and a single dad but he doesn't stop there. He tells Katy Toby slept in his car, which creates an uncomfortable silence between the three of them.
When Toby Comes Back From Costa Rica
No one was more thrilled than Michael when Toby decided to quit Dunder Mifflin and move to Costa Rica in the fourth season. It seemed random but Toby was looking forward to Costa Rica's island vibe in comparison to Scranton's.
But after Toby broke his neck while zip-lining, Toby returns to Scranton where he gets his job back. Michael was unaware Toby came back and was horrified when he saw him in the office. He began screaming "No! God, No!" while Toby awkwardly stood there.
The Caprese Salad Drug Bust
When Toby came back from Costa Rica in the fifth season, Michael would do anything to get him to leave. And since Toby wasn't going to quit on his own, Michael decided the only way to get him out of the office was to frame him. He went to the warehouse where he hilariously bought $500 worth of marijuana and hid it in Toby's desk.
He and Dwight then called the police to give them the tip that Toby brought drugs back from Costa Rica. But when the police searched Toby's desk, all they found was a bag full of Caprese salad... Michael is so pure that he didn't realize that what he bought wasn't drugs... it was basil and cheese...
When Michael Scarn Killed Toby
Threat Level Midnight was the screenplay Michael had been working on for years. When it came time to film the movie, he had everyone from the office participate. In the seventh season, the movie was ready for viewing and everyone huddled together in the conference room to see the final result.
In the film, Toby plays a hostage whose head gets blown up after Michael Scarn shoots him. Toby's head exploding is then shown six different times after it happens, which Michael claims was the most expensive part of the movie was "integral" to the plot...
That Time Toby Opened Up About His Parents Divorce
In the episode "Deposition," Michael is asked to help Jan in her lawsuit against Dunder Mifflin for wrongful termination. Sadly for Michael, Jan threw him under the bus in multiple ways, making him realize he loved his company more than his girlfriend.
After a hard deposition, Michael and Toby awkwardly eat lunch together because they're the only people they know in the lunchroom. Toby used this moment to tell Michael he knew where he was coming from. He was also put in a difficult situation when his parents got divorced. The moment was sincere and raw but before Toby could finish, Michael slides Toby's lunch off the table and leaves before another word is said.
Michael's Going Away Present For Toby
In the episode "Goodbye, Toby," Michael decides to throw a ginormous party to celebrate Toby's departure from Dunder Mifflin. It was essentially a mini carnival. However, what Michael didn't expect was for Toby's replacement (Holly) to show up on the same day and to be so appealing and sweet.
Realizing he had a crush on her, this made everything more uncomfortable when she sat in on Michael and Toby's exit meeting... Michael had an entire speech prepared for Toby about how much he disliked him but Holly interrupted his plan. Things got worse when Toby opened up Michael's gift to him and it was a rock that said: "Suck on this!"
Six Hours Of One-On-One Therapy
In the episode "Counseling," it's Michael's nightmare when he's forced to do six hours of one-on-one counseling with Toby after he physically assaults his nephew in the office. Not wanting to spend more than one day with Toby Flenderson, Michael wants to crush the six hours in one day. But after one hour not saying a word to Toby, he tells Michael he won't complete the session until Michael talks to him. This is Michael's nightmare.
To get Michael more comfortable, he adds games and child-like activities for Michael to do to open him up, and it worked! However, the awkwardness and the tension between Michael and Toby could be felt through the TV screen.
Toby's Radon Speech
"The Chump" has one of the most uncomfortable scenes in Office history. Toby tells the office he's putting Radon test kits around the office and to not touch or tamper with them. (Michael, of course, ignores this and thinks their ant traps.)
Michael becomes sick of Toby's speech and tells him "If I had a gun with two bullets and I was in a room with Hitler, Bin Laden, and Toby, I would shoot Toby twice." Michael took it too far with this one. Even Dwight said so!
Casino Night
"Casino Night" was an iconic episode for a multitude of reasons but it was also an uncomfortable episode for Michael and Toby. Michael wanted to host a casino night to benefit a charity of someone's choice, which ended up being the Boy Scouts of America. At the end of the night, Michael was going to give the check to a bunch of Boy Scouts to see them smile.
But, considering there's gambling involved, it was a school night, and it was catered by Hooters, Toby shut that idea down quickly, which triggered Michael. Things got worse between the two when Toby beat Michael in a game of Texas Hold 'em.
Michael's Complaint Files
In "Conflict Resolution," the office becomes divided when everyone's conflicts with one another become out in the open thanks to Michael's nosiness. The conversations between Toby and Michael become conflicts themselves and we find out that Toby has a completely different file for complaints against Michael (which Michael didn't know about).
Toby shows the camera the folder and the January through March file was already jam-packed with complaints, proving that Michael isn't as conflict-free as he thinks.