Season 3, Episode 14
From the beginning of “The Office,” there was no better partner in crime than Pam for Jim’s antics. By Season 3, even Pam and Jim knew that — but circumstances had conspired to keep the couple away from each other. And although Jim and Karen Filippelli had chemistry, in “The Return,” Karen’s not keen on Jim’s plan to hide Andy’s cell phone — and drive him nuts by continually calling it. Pam, however, was all in on the prank. Karen had already suspected that Jim hadn’t worked through his unrequited feelings for Pam — and to his credit, when Karen confronts him on it, he quietly cops to it. This wasn’t the end of Jim and Karen, but it continued to set the stage for an obvious break between the two, and the eventual return of “Jim and Pam” as a thing.
Season 3, Episode 20
Not only does this episode feature perhaps one of Krasinski’s funniest ever moments on the show — the cold open, in which Jim’s flawless impression of Dwight sends the latter into a fiery rage — but later scenes spotlight Jim’s ability to put aside his occasional annoyance with his co-workers and find room for empathy. The final beats of his storyline with Andy, who’s just received some devastating news about a relationship he thought he was in (with a high school student), reveal Jim’s innate compassion, as well as a pretty decent singing voice.
Season 3, Episode 23
In the episode previous to this one, “Beach Games,” an empowered Pam tells off most of the Dunder Mifflin staff while saving most of her ire for Jim — noting that she called off her wedding because of him. But what hit Jim the hardest was Pam’s admission that she missed their friendship. Now, in “The Job,” it’s Jim’s turn to make a grand gesture. Interviewing for a management position in New York, Jim realizes that he has no interest in moving with Karen (who was also a contender for the gig) to the Big Apple. Instead, back in Scranton, he asks Pam out for a date. It was the end of Season 3, but the start of a whole new storyline for Jim and Pam. Krasinski is even seen with a new haircut — which he had gotten for a movie role but also worked as a signal that a new Jim was here, and that “The Office” was done playing games: “Jim and Pam” was here to stay.
Season 4, Episode 6
Jim has limits, and though it’s not often we see him as a buzzkill, it’s important to note that Jim isn’t willing to be a jokester at the expense of someone’s feelings. Dragged to Utica by Michael and Dwight, the trio is out for vengeance after Stanley gets poached by another Dunder Mifflin branch. That means taking on Jim’s ex-girlfriend, Karen. Obviously, Jim doesn’t want to go at all, but he stays with the team in order to keep the two loose cannons in check. “This is the dumbest thing we’ve ever done,” Jim says, and later, he’s forced to explain himself to an angry ex, colleague, and superior. It’s a deserved moment for Karen, who disappears without a trace after Jim and Pam get their happy ending, even if Jim doesn’t fully deserve the scolding. Krasinski plays embarrassed and scared for peak hilarity, but it’s his reunion with Pam after returning home that really emphasizes the kind of man Jim is: a good one.
Season 5, Episode 1
Jim as a character was all about the big dramatic gestures, which is why his proposal to Pam in the Season 5 premiere came as such a surprise, as he simply gets down on one knee during a rushed rendezvous at a roadside gas station. But even when filmed from a distance, through the rain, Krasinski is able to sell all the pent-up passion and love he’s been carrying with him for years, making this moment not just a cathartic one for romantics, but for anyone who had come to care for Jim as a character.
Season 5, Episode 28
In an episode with Idris Elba, Rob Huebel, James Urbaniak, and the triumphant return of Amy Ryan as Holly Flax, it takes a lot to break through. Jim and Pam masterminding a plot to get everyone home early by setting all the clocks forward (2009 was such a simpler time) comes close, though, as does Pam’s smirking reveal that she can play a little volleyball. The kicker, though, is another classic season-closing Jim/Pam moment, as the two of them find out that she’s pregnant. Jim finding out is a lovely beat, sold by a lovely bit of wordless acting from Krasinski and Fischer. That big grin and those welling eyes tell more than any cheesy line of celebratory dialogue ever could.
Season 6, Episodes 4 & 5
Here, Jim gets the girl in an hour of television that runs the gamut from tears to laughter to dance numbers to happily ever after. It’s not a perfect wedding, thanks in no small part due not just to the expected antics of the Dunder Mifflin family, but Jim blowing his and Pam’s big secret (that she’s already pregnant). However, he recovers nicely from that massive slip-up with two weddings for the price of one — emotionally, anyway — capped off by one of Jim’s most romantic talking head moments: “I bought those boat tickets the day I saw that YouTube video. I knew we’d need a backup plan. The boat was actually Plan C. The church was Plan B, and Plan A was marrying her a long, long time ago, pretty much the day I met her.”
Season 7, Episode 6
Jim doesn’t do Halloween costumes. Prior to Season 7, his most elaborate look is Three-Hole Punch Jim, followed closely by the time he wore a name tag with “Dave” written on it. But when he finds out Danny (Timothy Olyphant) never called Pam back for a second date because she was “too dorky,” he realizes why it’s so important for her to have a man in full Popeye costume standing next to her Olive Oyl. Jim earned never-ending good boyfriend points over the course of the series, but this example from late in the game introduces a tinge of jealousy to the proceedings, as well as another mature move from a character often perceived to be childish.
Season 8, Episode 13
What “Jury Duty” does as an episode that feels relatively essential to Jim’s arc as a character is the reveal of just how awkward he initially found family life. After choosing to lie to the office about why he was absent for a week — his “jury duty” lasted half a day, and he spent the rest of the time at home helping Pam with the kids — Jim tries to orchestrate a cover-up with the help of Andy. But his final gambit backfires when he brings his two young children into the office, and we see that as often as smooth as Jim can be, when it comes to fatherhood he’s still more than capable of helpless floundering.
Season 9, Episode 11
When Daryl comes to interview at Jim’s sports startup, it’s our first glimpse into the Philadelphia office, but more importantly, it’s our best look at what Halpert’s professional future looks like. Happy, excited, and creative, Jim operates with confidence and a “real Facebook energy,” as Daryl describes the office vibe. Jim’s busy, sure, but he’s thrilled to be busy instead of beaten down by the work. It’s necessary for the audience to see what a difference a good environment makes for Jim’s life; after all, this is the company Jim and Pam move to Austin for at the end of the show. He wants this, and viewers needed to see why.