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The Office: 10 Times Toby Flenderson Broke Our Hearts

Toby Flenderson was The Office's resident sad sack. There were plenty of times that this poor guy's situation just broke our hearts.

Every sitcom seems to have that one character that always gets a raw deal. In The Office, that character is obviously Toby Flenderson. As the Human Resources agent in the office, Toby is often the one that has to put an end to all the wild and crazy activities. This makes him pretty unpopular and an archenemy of Michael.

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Despite being a kind and thoughtful person, nothing seems to go Toby's way. While it can be pretty funny watching him always be the butt of the joke, it's hard not to feel sorry for him every so often. Here are some of the times Toby broke our hearts.

10 Diversity Day

Michael's "Diversity Day" seminar is a legendary and cringe-worthy moment in the show's history. It is the perfect display of Michael's oblivious offensiveness and would surely have been an HR nightmare. However, Toby is excluded from the meeting before it even begins.

After making a harmless joke while entering the conference room, Michael ejects him from the meeting, unironically saying "This is an environment of welcoming and you should get the hell out of here." But Michael seems less angry about the joke and angrier that people found it funny.

9 Prize For Pam

Jenna Fischer as Pam Beesly in The Office

Toby has always had a pretty awkward love life. No failed romance is as uncomfortable as his secret love for Pam. Not being the most confident man on earth, Toby is unable to tell Pam how he feels so he tries to court her in subtle and ineffective ways.

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When the whole office goes out to a bar for happy hour, Pam makes a comment about a stuffed animal prize in one of the bar's games. Toby then spends the entire night trying to win the prize for Pam only for Pam to suggest he give it to his daughter.

8 Too Far

Michael's intense hatred for Toby is so over-the-top, it's hard not to find it funny. Michael is usually not such a negative person but he seems to dedicate all of his anger towards that one man. And sometimes he can go overboard.

While Toby is giving one of his boring talks to the office, Michael makes a joke at his expense, getting a laugh from everyone. He then says "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." Everyone agrees he went too far with that one.

7 Christmas Gift

Poor Toby. Even on Christmas, he ends up being the outcast of the office. During the office Christmas party, everyone is handed out their corporate gift which is a fairly nice bathrobe. But when Michael decides to give one of the robes to Holly, it means someone has to have theirs taken away.

It's certainly not surprising that Toby is the unlucky employee who doesn't get one, but the fact that he seems to be really excited about it before Dwight snatches it from him is really sad. Luckily, Pam gifts him with one in the end.

6 Framed

The day Toby leaves Dunder Mifflin is one of the happiest days in Michael's life. Predictably, he doesn't handle Toby's return very gracefully. In an effort to get rid of Toby for good, Michael plants drugs in his desk and calls the police.

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The dugs are actually just salad, but Michael doesn't know that. So when the cops arrive and search Toby's desk, we can see him get genuinely distressed that he is being framed. Even Michael knows the prank went too far and Toby is very shaken by the situation.

5 Beach Day

"Beach Day" is another classic episode from the show where the entire office gets to have some fun in the sun. Well, almost the entire office. Just as they are getting ready to leave, Michael informs Toby that someone has to stay behind and run the office.

Even though it is a ridiculous task, Toby sadly does as he's told. Watching him stay behind after getting so excited about the idea is truly devastating. It gets worse as the episode periodically cuts back and forth between the fun at the beach and Toby along in the office.

4 Sharing Lunch

Despite all the abuse and tormenting Toby experiences at the hands of Michael, he remains a total professional. Not only that, Toby actually tries to help Michael out on several occasions. And he never gets any respect in return.

After Michael has a terribly embarrassing deposition at the corporate offices, he is forced to have lunch with Toby. Right away, Toby is sympathetic and understanding to Michael. He even mentions how he went through similar things with his divorce. In response, Michael pushes Toby's food off the table.

3 Counseling Michael

The Office Michael Scott Toby

After Michael goes a little too far in disciplining a disruptive employee, he is ordered to undergo counseling. Much to Michael's horror, the counselling is provided by his very own HR officer.

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Michael is obviously quite childish throughout the entire counseling session, refusing to participate at all. However, Toby proves to be quite effective and gets Michael to open up about his past. When Michael realizes he was tricked, he lashes out at Toby in a pretty brutal fashion.

2 Speaking To God

Toby seems to spend most of his life getting kicked around. He has been divorced, he has been unlucky with other relationships, and he is mistreated at work. All that most start to weigh on a person and make them question why so many bad things happen to them.

When the office goes to the christening of Jim and Pam's baby, Toby hesitates to go into the church as it has been a long time since he talked to god. After summoning the courage, he finally walks in a says, "Why you always gotta be so mean to me?"

1 Costa Rica

After abruptly deciding to move to Costa Rica, there was a glimmer of hope that Toby might actually start to find happiness in life. He is leaving everything behind and escaping the mundane working world to have some fun for once in his life.

After being gone for some time, we get to check in on his new life in Costa Rica. He is shown in a hospital bed with several broken bones. He explains that he broke his neck in a ziplining accident shortly after arriving. Poor Toby.

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