One of Ryan’s cringiest moments in The Office is deeper than it seems — and surprisingly brilliant    

The Office remains one of the few shows that depict the excruciating comedy of workplace life. It stands as a cultural milestone due to its iconic lines and ensemble cast while simultaneously managing to make its audience laugh and cringe at the same time.

One of the most awkward moments of the show has to be in Season 3 Episode 12, titled “Traveling Salesmen,” when the desperate and self-important Ryan Howard face plants during a sales call with a client. He documents the moment that would go on to be immortalized as the epitome of cringe. However, upon deep analysis, it serves as a gentle, yet ingenious exploration of the characters that the show has to offer.

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Ryan and Stanley: The oddest couple in a corporate comedy

In this episode, Michael Scott, in an attempt to foster team cohesion, decides to pair up his sales staff for a day of combined sales calls. Like always, everything goes awry.

The least likely pair is Stanley Hudson and Ryan Howard. Stanley is a grumpy crossword enthusiast who works at Dunder Mifflin’s Scranton branch, and he seems to be painfully bored with the entire exercise. After a bit of grumbling, he gives in with an exasperated sigh and a droll, “Fine. I’ll take the kid.” What follows after that is one of the most awkward and brutal, though enlightening, scenes in the entire series.

Stanley goes to the client’s meeting, but is barely present. Bending over a crossword puzzle, he proceeds to tell the group:

“I’m going to let Ryan do a little pitch for you.”

Executed in a shaky voice and to visible unpreparedness, Ryan means to say “Hi” but ends up freezing up instead. It is indeed the silence that follows. He always seems to falter or stutter through the barrage, blowing it up. Without any useful insight to provide, Stanley eventually steps in. He seals the deal effortlessly, showing exactly why he is still one of the top salesmen in the office.

In essence, every second of the scene is dedicated to comical moments depicting Ryan's incompetence while flaunting Stanley's smooth competence. However, a deeper dive uncovers yet another perspective, shocking enough for one to take note of.

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Was it a setup — or a stealth mentorship?

Initially, it may appear that Stanley’s selection of Ryan as his partner was based primarily on the fact that Ryan was the least obnoxious option. After all, Andy Bernard was the other option. But there is a compelling theory worth taking a look at: what if Stanley was not putting up with Ryan, but rather putting him through his paces?

The client they go to visit is clearly one that Stanley has interacted with before–a seasoned clientele comprised of business owners with whom he has a rather fluid and friendly relationship. That dynamic is what turns the situation on its head. Stanley did not take Ryan to a high-stakes meeting.

He took him to what is called a comfort zone—the safest space where even disastrous performances would not result in outcomes that would go haywire. It was a no-lose scenario, where if Ryan came out victoriously, it would be wonderful; if he, as expected, falters, which he did, Stanley would have the means to salvage the deal without damage.

In response to Ryan's possible disastrous performance, instead of offering a guiding hand or advice, and telling him what to do, Stanley orchestrated a crash course in sales using the most fired-up approach: toss the temp into the deep end, allow him to flail any way he wants, but be ready so he doesn’t drown.

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Comedy that cuts deeper than expected

The comedy still lands: Ryan's body language is awkward, and he is terrified to make basic eye contact, which results in a silence that is deafening — all these factors coalesce into quintessential deadpan yet cringeworthy humor. Still, the possibility of an underlying intent adds emotional depth and richness to the narrative.

Aligned with the rest of the characters above drama, it’s easy to forget the negative. In reality, all that provides him with the emotional motivation that will catapult him any further in his career is going to take a lot more than mere clichés. “Traveling Salesmen” might be the first instance that forces him to confront his own limitations, which, although quite excruciating, could be equally fundamental.

As for Stanley? In true style, he neither confirms nor denies anything. Regardless of the purpose—trying to guide Ryan, not guiding him based on indifference, or letting go of his autonomy, the outcome remains unchanged—learning the hard way.

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Final thoughts: Growth hides in the cringe

The brilliance of The Office is in how it blends authentic character development within the realm of what appears to be ridiculous—a sales pitch gone wrong and an icon in the making become an unspoken lesson. Even the office curmudgeon, who wishes to be left alone, may have had a deeper influence than anyone expected.

This shows that the most effective educators are sometimes the ones who don’t coddle you. They allow you to delve deep into a corner and ensure that, when it’s necessary, you’re granted a means to escape.