The Office Superfan Episode That Features Jim's Most Hypocritical Moment

Jim Halpert (John Krasinski) is a fun goofball and a lovable guy. While he just makes the cut for one of the top 10 best characters from "The Office," though, he has his fair share of questionable moments. In fact, he's done some pretty bad stuff. The guy can be sarcastic. He antagonizes his co-workers when he wants to. He drives girlfriends like Karen (Rashida Jones) and Katy (Amy Adams) crazy with his clear feelings for Pam (Jenna Fischer). Heck, he even kisses Pam when she's engaged. He spends most of Season 9 acting like a jerk of epic proportions and almost torpedoes his marriage in the process. But there's one moment, a few seasons before that, where Jim utters his most hypocritical line of all.

In the Season 6 Superfan episode "Secret Santa (Extended Cut)," the camera pans over to Jim and Pam standing in the doorway to the office kitchen. Pam says, "This is a great party. Did you buy the company just to save your Christmas party?" to which Jim replies, "I promise I will never buy a company without telling you first." The issue? Jim does precisely that three years later.

Let's get a little context. Dunder Mifflin has just been acquired by an unknown buyer. This leads to a brief spell of anxiety, bordering on panic, until the staff realizes they are the reason the acquisition happened and their jobs are secure. From there, the Scranton branch gets back into a festive spirit, which leads to Jim and Pam's banter about their mysterious buyer. (It ends up being Jo Bennett's (Kathy Bates) Sabre, but that isn't known until later.) Jim's words come and go without a second thought — that is, until three more years go by.

At first glance, Jim's line about telling Pam before he buys a company is a cute and purely hypothetical exchange. However, when the chips are down, it turns out to be an empty statement. Jim makes his initial promise halfway through Season 6. Less than three years later, in the Season 9 premiere, "New Guys," Jim commits to being a founding member of the sports marketing startup Athlead. He invests thousands of dollars as a founding member, too. You know what else? He doesn't tell Pam until after the deed is done. Even worse? She was aware of the job offer and had said she didn't want Jim to pursue it.

The entire scene is already not cool. Jim commits to something that puts the financial future of his family in jeopardy, and will require him to head to another city on a regular basis for work. On top of prioritizing personal ambition over family and marriage, though, it turns out that Jim had literally promised not to do that exact thing. Three years earlier, he had told Pam that he would never buy a company without telling her — and then he goes and founds one behind her back, committing significant time, money, and emotional resources to a venture without letting Pam in on his secret. No wonder the couple's Season 9 story arc is so rocky. It doesn't just come from a moment of indiscretion. It is precipitated by the erosion of trust built on years of promises, and turns one of Jim's most endearing lines into one of his most hypocritical moments.