It really sucks when you constantly get walked over by almost everyone, despite being one of the coolest and most soft-spoken people at your office. No matter what you do, no one likes you. This is the life of Toby Flenderson, a fictional character from the NBC sitcom TV series, The Office. He is a human resources representative for the Scranton branch of the paper distributor Dunder Mifflin, who is perceived by many of the company’s employees as the arch-enemy of branch manager Michael Scott.
Toby Flenderson is portrayed by Primetime Emmy Award-winning actor, screenwriter, TV director, and producer, Paul Lieberstein. Here are some of the most interesting things you need to know about the character.
Fast Facts About Toby Flenderson From The Office
1. He Testified Against His Parents As A Child
When he was a child, his parents divorced, and he was compelled to testify against both of them. This childhood experience traumatized him, which is why one of the key elements of his character is his troubled childhood.
2. Toby Flenderson Is Well Educated
Toby Flenderson is highly educated. He attended Bishop O’Hara High School before proceeding to Pennsylvania State University. He also earned a Bachelor of Science degree from California Coastal College and a degree in Social Work from Temple University.
3. He Dropped Out Of The Seminary
The first thing to know about Toby Flenderson is that he is a former seminarian. He attended the seminary for a year before dropping out. The reason he left was to have s*e and/or a relationship with a girl named Kathy (though she never appeared in the series). He eventually married her, and they had a daughter named Sasha together.
4. Flenderson And Kathy Divorced
Unfortunately, Flenderson’s marriage to Kathy didn’t last, ending in a divorce that caused him significant trauma. The divorce brought him so much pain that he is often angry. His anger stems from feeling isolated and alone, and from not being able to see his beloved daughter as often as he would like.
5. His Daughter Sasha Is Fond Of Michael Scott
Toby Flenderson’s primary tormentor at the office is Dunder Mifflin’s Scranton branch manager, Michael Scott, who never hides his dislike for Toby. In contrast, Toby’s daughter, Sasha, adores Michael, which only adds to Toby’s woes.
6. He Had An Unrequited Crush On Pam Beesly
It’s awkward when you have feelings for someone and can’t express them openly. Flenderson had a crush on his co-worker Pam Beesly, but he wasn’t confident enough to tell her how he felt. Instead, he tried to show his affection in subtle and ineffective ways. For example, during a happy hour at a bar with the whole office, Pam rejected a stuffed animal prize he won, suggesting he give it to his daughter, despite initially commenting on it.
6. He Writes Crime Novels To Escape His Reality
As mentioned, Flenderson is treated poorly by Michael Scott and other colleagues. His love life is dry, and his divorce, along with not being able to see his daughter as often as he would like, affects him negatively. Unfortunately, he doesn’t share his problems or frustrations with anyone, so he bottles them up. One way he escapes from all these is by writing crime novels. He believes the novels will become a success someday.
7. His Crush Pam Beesly Married Jim Halpert
While Toby Flenderson secretly had a crush on Pam Beesly, she was Jim Halpert’s love interest. Flenderson was shattered when she eventually married Halpert in season 6 of the show. He was even more devastated when she gave birth to a daughter, Cece. Although he was invited to the christening, he refused to enter the church, feeling that God was being mean to him.
8. Flenderson Moved To Start Afresh But Ended In A Hospital Bed
Since nothing seemed to work in his life, Toby Flenderson decided to move to Costa Rica, hoping to find happiness and fulfillment there. Unfortunately, tragedy struck immediately after his arrival. He had a terrible accident and ended up in a hospital bed with several broken bones.
9. He Became An Author After He Was Fired From His HR Job
Flenderson returned from Costa Rica and resumed his job as the Human Resources representative after Holly Flax, who had temporarily replaced him, was transferred. He was fired at the end of season 9 and moved to New York City, where he became an author.
10. Paul Lieberstein Played Toby Flenderson
Paul Lieberstein portrayed the character of Toby Flenderson. Initially, he was one of the show’s original writers and also served as the showrunner at one point. He eventually landed the role because the show’s director, Greg Daniels, felt that acting was crucial to developing better writing.
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