Ryan’s 10 Biggest Mistakes on The Office

Ryan's 10 Biggest Mistakes on The Office

As a long-time observer of Dunder Mifflin’s colorful characters, I must say that the life of Ryan Howard is a rollercoaster ride of failures and missed opportunities, much like the infamous Dunder Mifflin Infinity overhaul itself. From his jumbled pitch with Stanley to committing fraud, and even abandoning his own child at a wedding, it’s clear that Ryan struggles with accountability for his actions.


B.J. Novak’s character, Ryan Howard, portrayed by one of the co-writers and producers of The Office, is undeniably hilarious yet hard to root for. His shifting personas throughout the series, coupled with his tumultuous relationship dynamics towards Kelly and her romantic interests, along with his misguided aspirations, consistently elicited laughter from viewers during the show’s nine seasons.

viewer’s hearts go out to Ryan as they eagerly follow his quest for redemption. Regrettably, the show The Office doesn’t provide a resolution to Ryan Howard’s redemptive storyline, yet it keeps audiences captivated by the series of humorous blunders that Ryan continually commits instead.

10 Ryan Started the Fire

Season 2, Episode 4 – “The Fire”

Ryan's 10 Biggest Mistakes on The Office

In the fourth episode of the second season, named “The Fire,” Ryan mistakenly ignites a blaze in the office. This occurred when he placed his pita bread into the toaster oven, not realizing it had been inadvertently switched to the oven setting, causing it to catch fire promptly.

Following the evacuation of the office, Dwight composes a tune inspired by the incident, mimicking the style of Billy Joel’s “We Didn’t Start The Fire.” The lyrics humorously assert “Ryan ignited the flame, Smoldering since the world began spinning!” Subsequent verses take playful digs at other coworkers, and Dwight and Michael perform a lively rendition of the amusing parody in the parking lot, celebrating Ryan’s faux pas.

9 Antagonizing Jim

Season 6, Episode 11 – “Shareholder Meeting”

Ryan's 10 Biggest Mistakes on The Office

When Jim ascends to the role of Co-Manager at Dunder Mifflin’s branch, Ryan persistently provokes Jim in his new position. Ryan also harbors the notion that, due to the company’s financial struggles, he can skimp on work and spread rumors about Jim’s authority within the office to divert the attention of other employees.

Following repeated instances of Ryan’s lax behavior and persistent teasing, Jim decides to assert his power by assigning Ryan a small office space – a closet. However, due to the widespread dislike towards Ryan, no one takes initiative to remove him from the closet. This further amplifies Ryan’s embarrassment, as no one steps in to aid him.

8 Becoming a Substance-Addicted Party Boy

Season 4, Episode 15 – “Night Out”

Ryan's 10 Biggest Mistakes on The Office

Following Ryan’s advancement to Vice President of Dunder Mifflin Northeast Sales in season 4, it becomes evident that he swiftly immersed himself in the social circle and substance abuse habits of the corporate bigwigs. In the 15th episode of season 4, Michael and Dwight accompany Ryan on a New York trip for partying.

At a party, we see an individual named Ryan, who struggles with substance addiction, veering off on random, nonsensical tangents that leave everyone puzzled. At one point, he even throws his drink onto the floor in a fit of agitation. Although the series doesn’t specify what substances Ryan uses at his new job, his erratic and unpredictable behavior due to these substances makes it impossible for him to conceal his personal flaws. His decision to join corporate life and attend such parties ultimately leads to him becoming even more intolerable, particularly during his comeback to the Scranton branch.

7 Asking Out Pam Multiple Times

Multiple Episodes

Ryan's 10 Biggest Mistakes on The Office

In The Office, Ryan persistently attempts romantic advances towards nearly every woman he encounters, except for Kelly. Despite knowing that Pam is involved with Jim, Ryan repeatedly expresses interest in her romantically.

When Ryan ascends to a higher position and returns to the Scranton Branch to present his Dunder Mifflin-Infinity concept, he takes a glance at some logos designed by Pam. Ryan expresses genuine praise for Pam’s work, though not without a hidden agenda. Following their review of the designs, Ryan requests additional time to evaluate them further, which she consents to.

However, this quickly turns into a romantic advance as Ryan asks Pam if they could discuss this over dinner that night. Pam and Jim quickly intervene, revealing their very obvious relationship with Ryan. This isn’t the only time Ryan has tried to steal Pam from Jim, but it is one of the most awkward moments by far.

6 Getting Accused of Flirting with Stanley’s Daughter

Season 2, Episode 18 – “Take Your Daughter to Work Day”

Ryan's 10 Biggest Mistakes on The Office

In the “Take Your Child to Work Day” episode, Stanley Hudson brings his daughter Melissa Hudson to the office. It doesn’t take long before the 8th grader becomes smitten with Ryan. Despite not feeling the same way, Ryan still interacts with her, which ultimately leads Kelly to spread a rumor that Ryan was flirting with her.

In an instant, Stanley swiftly corrects Ryan’s behavior, leading to a hilarious sequence in the series where he suggests Ryan has lost his senses, needs divine intervention, and warns him not to repeat the action under any circumstances, or face more severe consequences.

At a later point in the series, Ryan bumps into Melissa once more at a corporate event. However, he doesn’t recognize her. Consequently, Stanley gets into a scuffle with Ryan, this time taking place in the ladies’ restroom of a restaurant, while Toby remains engrossed in a claw machine game, seemingly indifferent to the significant HR issue brewing in an adjacent room.

5 Kelly

Multiple Episodes

Ryan's 10 Biggest Mistakes on The Office

Following their first Valentine’s Day encounter, Ryan repeatedly attempted to end things with Kelly, but each effort failed. Instead, Kelly only expressed her affection for Ryan more strongly. It wasn’t until he received his New York promotion that Ryan was finally able to end the relationship, temporarily resolving the “will they stay together or not?” dilemma.

At this difficult time, he bluntly states, “We’re over.” This temporary liberation feels good for Ryan, but when he resurfaces after his arrest, shame takes hold as he finds himself resentful towards Kelly’s budding relationship with Darryl. Yet, this seemingly unfolding sequence of events was orchestrated intentionally, for Kelly feigns a pregnancy in an attempt to lure Ryan back into her life. Despite Ryan’s actions concerning Kelly, their storyline usually results in torment and humiliation for him.

4 The Dunder Mifflin Infinity Pitch

Season 4, Episode 3/4 – “Dunder Mifflin Infinity”

Ryan's 10 Biggest Mistakes on The Office

The proposal for Dunder Mifflin Infinity presented by Ryan is the catalyst for his subsequent professional decline within the corporate structure. This is because his vision of modernizing the paper company fails to gain traction, leading him to falsify the performance data of the new initiative. During the presentation itself, Michael consistently challenges Ryan’s ideas due to his discomfort with someone having control over what the Scranton branch can do.

As a movie buff putting it in my own words, I’d say: “The Dunder Mifflin Infinity overhaul clearly shows it’s doomed to flop, with a clumsy and muddled plan that just doesn’t work. Yet, Ryan persists in making poor decisions, even resorting to fraud – a clear sign he refuses to take responsibility for his shortcomings.

3 Ryan’s Failed Pitch with Stanley

Season 3, Episode 13 – “Traveling Salesman”

Ryan's 10 Biggest Mistakes on The Office

In truth, Ryan hasn’t been great with presentations, but this particular attempt was undeniably quite awkward for him. To make matters worse, he requested assistance from Stanley because it was one of his initial sales calls. However, what Ryan failed to grasp was that all the clients were actually friends of Stanley.

Ryan feels immediately overwhelmed by the clients, while Stanley leaves him alone for his crossword puzzle. All that comes out of Ryan are a series of squeaky “Hi’s” as he tries to make a sales pitch. The sales call ends unsuccessfully, causing Stanley to burst into laughter at Ryan’s discomfort. He even jokes that Ryan is like his 6-month-old niece who only says “hello.” This moment is particularly satisfying for Stanley, as it’s one of many where Ryan makes a fool of himself.

2 Committing Fraud

Season 4, Episode 19 – “Goodbye, Toby”

Ryan's 10 Biggest Mistakes on The Office

At the end of season 4, titled “Goodbye, Toby,” it comes to light that while holding the position of Vice President at Dunder Mifflin’s Northeast Sales, Ryan had been falsifying sales figures on the Dunder Mifflin Infinity website. Consequently, he is taken into custody for his involvement in fraud.

Following a significant rise within Dunder Mifflin, Ryan was exposed for fabricating sales figures, leading him to depart in season 5 and take over Pam’s role. However, even while working as a receptionist back at the office, Ryan continues to evade responsibility for his arrogant behavior and its part in the company’s decline.

1 Abandoning His Son

Season 9, Episode 25 – “Finale”

Ryan's 10 Biggest Mistakes on The Office

Amongst the gravest errors made by Ryan, such as fraud and arson, was leaving behind his own son, Drake Howard. In the final episode of the series, Dwight Schrute ties the knot with Angela, and the entire cast gathers together. This includes Ryan, along with his child born from a casual relationship.

At some point during the wedding celebration, the infant was cared for by Nellie Bertram. Since Nellie took the child under her care, it can be inferred that she eventually adopted Drake as her own.

Ryan did everything he did primarily to elope with Kelly, who was in a relationship with Ravi at the time. Despite eventually reuniting with Kelly after years of tumultuous off-and-on relationships, Ryan’s significant mistake and moral wrongdoing cannot be overlooked due to his abandonment of his child during his friend’s wedding.

Following their mutual decision to unite, Kelly and Ryan choose to elope, leaving behind their wedding. They then rush off to be with each other at last. The scene shifts to Nellie, now holding the abandoned Drake Howard. Yet, humorously, some fans suggest that this escape may have spared him from turning into a replica of the self-centered and sociopathic Ryan Howard.

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2024-09-08 21:02