The Worst Things Jim Halpert Has Ever Done

The Office would never have been as successful as it was without a handful of key characters and their striking personalities. Michael Scott's cringey yet endearing leadership, Dwight Schrute's competitive commitment, and Pam Beesly's adorable yet strong personality all infused the show with a vivacious energy from day one. 

And then, of course, there's Jim Halpert. The other half of the PB and J sandwich, Jim remained deeply involved in the show, literally from the first to the last scene. However, while the aforementioned characters were fairly straightforward in their identities, Jim's personality remained a bit harder to pin down over time. On the surface, he was the lovable hunk, the cool nerd with a penchant for basketball, and the guy with a Nixon nose that made him recognizable from a mile away.

But as the seasons rolled on, several less savory aspects of Mr. Halpert's temperament began to bubble up to the surface. While the man never took up the role of a proper antagonist, there have been several points over the years where Jim Halpert had a pretty bad attitude, made some awfully poor choices, and did some truly terrible things.

The last episode of season two, "Casino Night," is a classic. It's filled with humorous entertainment as the office takes some time to attend a fundraiser awkwardly hosted by Michael Scott. While the jokes come on thick, one of the most memorable moments of the entire story happens in the closing minutes as Jim finally builds up the courage to "put it all on the line" with Pam. He declares his love for her in the parking lot, only to be turned down cold, with Pam clearly implying that she's committed to her fiancé Roy. Did you catch that? Her fiancé.

While romantic declarations are already a bit of a nasty emotional curveball to throw at someone who's engaged to another person, it probably would've been fine if he hadn't straight-up gone and kissed her a few minutes later. Finding Pam in the office where she's talking things through with her mom on the phone, Jim decides to dive right in and steal a kiss. Engagement aside, the lack of consent or even a conversation beforehand makes the whole scene a bit uncomfortable, not to mention selfish.

For a man who's famous for his romantic charm, Jim actually has a bit of a nasty track record when it comes to relationships. Rather than being a kind, caring, thoughtful boyfriend for the woman he's currently dating, he ends up coming across as a man who is so obsessed with one person that he can't come through for anyone else.

Within four years, Jim callously dumps two different women as he remains endlessly hung up on Dunder Mifflin's Scranton receptionist. He begins by dating Katie—a relationship that he initiates, by the way—in the closing moments of the first season. Less than half a season later, in the episode "Booze Cruise," Jim breaks up with her (while staring at Pam, no less) by casually stating, "Let's break up." The cold line comes across worse than a text message.

Looking to build on this not-so-solid foundation, the salesman begins dating Karen during his time in Stamford and then convinces her to move with him back to Scranton. Before season three wraps up shop, he ditches Karen while in New York, only to drive back to Scranton and ask Pam out on a date. Jim's ability to leave his girlfriends in the dust is a bit alarming, to say the least.

While there's no doubt that Jim was head over heels for Pam from the get-go, there is a short period of time where none other than Miss Beesly herself got the brunt of Jim's negative behavior. We're talking about the period of time when Jim and Karen were dating in Scranton. While Jim clearly is in emotional turmoil, it doesn't change the fact that he's cold, distant, and at times, even bitter towards his future wife.

His feelings can be summed up in a stinger-of-a-line that he shoots at Pam during the episode "The Negotiation." In the aftermath of Roy's thwarted attack on Jim, Pam apologizes to Jim in the break room, declaring that her relationship with Roy is "completely over now." Jim laughs sarcastically before declaring, "We'll see. I'm sure you guys'll find your way back to one another someday." He may be rattled by recent events, but it hardly gives the dude the right to take out his frustration on Pam—especially since Roy attacked Jim because the salesman kissed Pam, not the other way around.

Another subtle jab that goes more unnoticed is the fact that just two episodes earlier, Jim completely skips Pam's local art show, an event that both Roy and Michael manage to attend. While Jim is faithfully supportive of Pam's artistic pursuits in the future, when she's on his bad side, the purposeful lack of interest is intense.

While there are plenty of smaller, more obscure ways that Jim has shown his troublesome side, there's one particular event that showcases his bad behavior more than most—the time he bought Pam a house without telling her. There's no doubt that Jim is a showman. Part of the reason he loves pulling pranks is because of the entertainment value they bring to everyone in the office. But the unchecked desire to "wow the audience" can be taken too far, especially when you're talking about something as big as where you'll be living (and paying your mortgage) for the next decade or more.

While Pam initially responds to the "big Jim gesture" with thankfulness, eventually it starts leaking out out that even the infinitely forgiving Pam Beesly wasn't thrilled by being cut out of the process. The issue comes to a head in the season nine episode "Stairmageddon," when Pam brings up the fact that he bought their house without telling her. Her tone leaves no doubt that it stands in her mind as a clear negative and something he shouldn't have been rewarded for. It's a big enough deal that by the finale episode not long afterward, she uses that very fact as fodder for her decision to sell the house and move the family to Austin...without Jim's knowledge.

Moving away from Jim's personal life for a minute, it's important to remember that The Office is a show that revolves around, well, an office. It's a workplace, a space for a business to operate. But that doesn't do much to motivate Jim Halpert, not by a long shot. From season one forward, Jim repeatedly demonstrates his lack of motivation to work hard at his job. He comes across as careless, uninterested, and clearly ready to move on at the slightest opportunity.

And this isn't just bluster, either. While he moves to Stamford in season three to get away from Pam, he also accepts a promotion to assistant regional manager (with no "to the" in sight, by the way). A couple of seasons later, he goes behind Michael's back in order to nab a promotion to "co-manager," seriously upsetting both Michael and Dwight in the process. Later in the season, when he finds he can make more money as a salesman, he ditches the leadership position to reclaim his desk in the bullpen. Whether he's avoiding his work or grabbing at any and every promotion, Jim's work ethic is hardly worthy of note.

While Jim has exhibited some fairly nasty work habits and romantic tendencies over the years, occasionally his more controversial side simply comes out in little spurts of selfishness or bad behavior. Case in point: his attempt to escape Michael and Jan's dinner party. The season four episode "Dinner Party" is one of the most lauded episodes of the entire show as Jim, Pam, Andy, and Angela are tricked into participating in a miserable evening at Michael and Jan's condo. 

At one point, Jim becomes so desperate to make a run for it that he comes up with a simple yet effective scheme to withdraw. He announces that he just got a message from his landlord saying his apartment flooded, and that he and Pam need to leave. When Michael points out that two people aren't needed for that, Jim pauses in consideration before deciding to save his own hide at all costs. He attempts to leave alone, leaving Pam to the wolves, only to be reluctantly dragged back in when Pam declares that he can always buy new stuff, but he "can't buy a new party." Poetic justice for such a low move, Mr. Halpert.

When it comes to lying, Jim Halpert is way too comfortable with the practice. In fact, the man's an addict. Along with lying to escape a dinner party from hell, he's constantly deceiving Dwight in order to lure him into one prank or another. He also has no problem keeping Michael in the dark when he goes for the co-manager position, and he's always leading him on by declaring his interest in things he had no intention of doing. Remember, Jim is the one who taught Pam to respond to Michael with the phrase, "Absolutely, I do."

He's even way too quick to pull the wool over his own partner's eyes. In season nine, he convinces Pam that he's extremely stressed while he's on the new job in Philly. While this is true to a degree, even Jim points out in the episode "Lice" that he's having the time of his life—after all, he's about to meet his personal hero Julius Erving—but that he needs to play it down as a "big meeting" in order to avoid rubbing it in Pam's face. Oh, what a tangled web of lies we weave.

Season nine really is a rough patch for Jim Halpert. It sees him stoop to all new lows as he selfishly chases a personal dream to the detriment of his family and coworkers alike. The whole situation starts when he decides to take a job with the startup company Athlead. While the company is Jim's brainchild, when his college friend initially approaches him to join the new enterprise, Jim and Pam collectively decide that he shouldn't do it. In spite of this decision, Jim ends up committing to the company behind Pam's back in the fading moments of the first episode of the season. 

Adding insult to injury, just a couple of episodes later, he decides on his own to invest $10,000 into the company, a much larger sum than Pam had signed off on. Jim's poor decision-making is clearly an issue here, but the more important concern is his rampant lack of communication with his wife, not to mention the complete failure to consider how the decision would impact his family as a whole.

While the entire Athlead experience showcases many of Jim's greatest character flaws, there are a couple of moments in particular where he really shows his dark side. The first one takes place during the season nine episode "Customer Loyalty." In this one, Jim is stuck at his new office, attempting to prevent a disaster as an investor attempts to back out from the company. In the meantime, he leaves it to Pam to record their daughter's dance recital. When Pam fails to film the event, Jim lashes out at her failure to come through, all the while blind to the fact that he's completely failing to come through for his family in the first place. 

The second moment of note comes shortly after in the episode "Vandalism." In this one, Jim and Darryl move in together as roomies in Philly while they work for Athlead. The match seems ideal at first, but it doesn't take long before the pair begin rubbing each other the wrong way. While Darryl is grumpy and irritable throughout the episode, Jim just vents his increasingly uncontrollable hostility. The most telling moment is when Darryl confronts Jim over using his clearly-labeled travel mug. Rather than simply return the cup, Jim goes into full-jerk mode and slowly pours the contents into a trash can, all the while staring directly at Darryl. While he's understandably under a lot of pressure, Jim the Entrepreneur doesn't do much for the character's reputation.

If one thing defines Jim more than his relationship with Pam, it's the endless string of epic pranks he pulls on Dwight. At least, we like to call them all "pranks." The truth is, the man totally antagonizes the beet farmer all of the time. From snowballs to the face and mocking his appearance to messing with his mind and tampering with his personal things, Jim has nothing short of a vendetta against his desk-clump mate. At the end of the day, it's honestly hard not to categorize the behavior as anything less than straight-up bullying.

Jim also regularly antagonizes Michael, even if it's in less obvious ways. He avoids Michael's attempts at friendship, keeps his boss at arm's length whenever possible, and doesn't hesitate to stoop to even lower levels, like having everyone read aloud and mock Michael's script for Threat Level Midnight. He's even the one who throws off the premiere of the final film when he breaks down laughing during a serious scene.

While no one is arguing that Jim doesn't have a ton of positive qualities, the man certainly has some significant flaws, no matter what way you slice it. Whether it's taking the job at Athlead, torturing Dwight, or lying to Pam, Jim Halpert certainly isn't quite the golden boy he's often made out to be.