10 Things About Toby Flenderson That Make No Sense


Toby Flenderson was the sad-sack HR rep for Dunder Mifflin Scranton, but what doesn’t make sense about this character from The Office?

The Office is full to the brim with some of the most imaginative and memorable characters in sitcom history. From the bumbling manager Michael Scott to the lovable girl-next-door Pam Beesley — there’s no shortage to the sheer number of characters that have made their mark in television history with their infectiously charming performances.

RELATED: Ranked: All Seasons Of The Office

One such character who has served as a punching bag of sorts throughout the office — especially for the aforementioned Michael Scott — is none other than Toby Flenderson, the sole member of HR who tries his hardest to make the characters of The Office listen to a much-needed voice of reason, to no avail.

While Toby might seem like a fairly innocuous character for the most part, there are some inconsistencies about him upon taking a closer look.

10 As A Member Of HR, He Is Ridiculously Ineffective


The whole point of having a Human Resource department is for the employees to remain satisfied and for the organization to follow a set of preordained guidelines in order to avoid any unnecessary controversies.

Anyone who’s seen The Office can attest to the fact that Toby definitely failed spectacularly in this regard since he barely did anything to maintain proper conduct in the office.

9 Jan Ends Up Doing The Bulk Of Toby’s Work

Jan in The Office

The fact that corporate had to send Jan time and time again to deal with Michael’s inappropriate behavior and callous management is a testament to the fact that Toby was absolutely useless as a representative of HR.

At this point, Toby should’ve either been transferred or fired, since he clearly wasn’t doing anything substantial in the Scranton branch.

8 His Behavior With Pam Is Wildly Inappropriate

For someone who works in HR, Toby has shown a penchant to be ridiculously creepy at times, to the point where it’s a wonder why his behavior had never been reported.

RELATED: The Office: 5 Characters That Became Parodies Of Themselves (& 5 That Had Great Character Development)

Take his obsession with Pam for starters — it was clear from his words that he used to stalk Pam, which was ridiculously unsafe for the then-receptionist.

7 Nellie Should’ve Reported Him For Harassment Too

The Office Nelly and Toby

Pam isn’t the only woman who felt uncomfortable around Toby — Nellie Bertram had also been subject to his creepy behavior at times, too.

Sure, it’s true that Nellie kissed him first… but that was in order to shut Toby up about the Scranton Strangler.

6 His Obsession With The Scranton Strangler Is Ridiculous

Jury duty is mandatory for everyone, and the fact that Toby lucked out and got an interesting case in the form of the Scranton Strangler doesn’t make it a topic of discussion for years.

However, this is exactly what he does — talk about the Scranton Strangler all the time and bores everyone to bits, to the point where Nellie has to go so far as to kiss him just so he could shut up for one moment.

5 It’s Sad That He Doesn’t Have Any Other Achievements To Talk About

toby the office

If there’s one thing that most people would know about Toby, it’s the fact that he has absolutely no achievements to talk about in his life.

From what people can glean given his appearances on The Office, there are only two things he’s proud of — being a juror on the Scranton Strangler case and being part of the documentary that was finally shown to the public in the final season.

4 It’s Weird That Michael Never Tried His Hardest To Fire Him

Anyone who’s seen The Office can attest to the fact that Michael absolutely hated Toby’s guts, and went out of his way to make life miserable for the sole representative of HR in Dunder Mifflin Scranton.

Given how much he hated the dude — coupled with the fact that Toby wasn’t really great at his job either — it’s weird how Michael never tried his hardest to kick Toby out of the office. Surely he had the grounds for it, personal reasons aside?

3 It’s Weird That Toby Didn’t Report Michael’s Behavior To Corporate More Often

The situation between Toby and Michael can be flipped too — Michael was unfairly harsh on Toby at times, to the point where one could qualify it as harassment.

This, coupled with Michael’s questionable behavior in The Office, gave Toby all the liberty in the world to report Michael to the higher-ups for his inappropriate behavior. However, he never takes this step, and Michael manages to get away scot-free with most of his injustices.

2 The Fact That Dwight Could Fire Him With Ease Is Hard To Digest

Dwight fires Kevin in The Office finale

Given the fact that Michael found it a massive challenge to fire Toby, it was assumed for the longest time that corporate was pretty much protecting Toby from being fired on unfair grounds.

So, keeping this in mind, it’s easy to wonder how Dwight managed to callously fire Toby at the end of the show without any major repercussions. Surely the problems that plagued Michael would’ve also affected Dwight when he tried to fire a member of HR, right?

RELATED: The Office: 10 Things About Dwight Schrute That Still Don’t Make Any Sense

Clearly not, since this firing happened with relative ease, making Michael’s struggles look downright stupid in comparison.

1 The Office Could’ve Been More Supportive Of Him

The Office Cast

While it was fun to look at Toby’s boring demeanor and dejected mood as just a character trait that could be made fun of, the fact of the matter is that Toby was actually an extremely lonely and depressed individual who had absolutely nothing going for him.

The cast of The Office is generally shown to be this tight-knit group of individuals who always support each other in their time of need. The fact that Toby was never privy to this support — barring some minor instances — is quite a shame. Out of all the people in The Office who could’ve benefited from some moral support, it was clear that Toby was on the very top of this list.

NEXT: The Office Meets Parks & Recreation: 5 Couples That Would Work (& 5 That Wouldn’t)

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Updated: November 8, 2020 — 11:00 pm

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