‘The Office’: The Best Jim and Pam Episodes

Out of all TV romances, the one between Jim Halpert and Pam Beesly on The Office might be the most celebrated of the last two decades. As played by John Krasinski and Jenna Fischer, respectively, having a chance to see their romance evolve slowly over nine years is still interesting to analyze.

Episodes that explored the romantic and dark sides of their relationship are always a matter of opinion. However, they had various key moments that are worth looking back on in a time when everyone is probably watching The Office again in quarantine.

What episodes best personify their relationship? A fan should probably go in chronological order again to be amused or gain insight on Jim and Pam’s relationship.

Jenna Fischer as Pam Beesly Halpert, John Krasinski as Jim Halpert embracing and smiling
Jenna Fischer as Pam Beesly Halpert, John Krasinski as Jim Halpert | Vivian Zink/NBCU Photo Bank/NBCUniversal via Getty Images via Getty Images

4. ‘Pilot’ (season one)

No better place to begin this than at the beginning where the first meeting of Jim and Pam was more than a little palpable. Nevertheless, it was not a romance meant to be yet. Pam was engaged to Roy Anderson, creating one of the most hilariously mismatched romances. Pam was stuck in a three-year engagement to Roy, creating a situation where Jim had to hide his feelings for Pam, according to Mashable. In the first episode, fans get a chance to see the blossoming of this and the problems it caused for a while.

At the same time, it also showed how bad relationships are often stuck in place. Pam really does not want to be around Roy, and yet he keeps imposing himself on her, making for a funny if ultimately sad situation. One thing for sure, though, is creating romantic tension in a TV show can sometimes create more viewer interest than when the couple finally gets together.

3. ‘Casino Night’ (second season finale)

RELATED ‘The Office’: Jim and Pam’s First Kiss Was Recreated for Season 3 With Small Changes

By the end of the second season, the flirting between Jim and Pam was becoming intense at times. Thanks to the documentary feel of the show, viewers could see how they were feeling internally based merely on expressions.

Yet, in ‘Casino Night,’ Jim finally expressed his feelings to Pam, according to IMDb. It only came at a time when he started to feel despair he had no real future at Dunder Mifflin. Jim was already feeling depressed that Pam was going forward with her marriage to Roy.

How Jim confesses his love for Pam is a true classic. After stating his feelings to her point-blank at the casino night event, Pam turns him down initially. Not until they encounter one another in the office again later do they finally kiss. Seeing Jim shedding a tear at the initial Pam refusal proved The Office could offer some seriously believable heartbreak outside the absurd office comedy.

2. ‘Weight Loss (Part Two)’ (Season Five)

Halfway through the run of The Office finds Jim and Pam’s relationship unfolding nicely. It reaches a point where Jim knows they need to become husband and wife.

Watching how he goes about it in the second part of Weight Loss is another great study in how to create magical romantic moments in a sitcom. Jim’s proposal still has to work around Pam’s schedule. At the time of this episode, she is taking a graphics design class in New York City, requiring some creative logistical moves by Jim to meet up with her.

When he does, he proposes to her outside a rest stop near NYC. On top of it, a massive rainstorm kicks in, creating a memorably funny if maybe typical romantic trope.

Their marriage leads to some surprising outcomes by the time the seventh season rolled around. Despite their marriage, the relationship between Jim and Pam stays interesting and never bores.

1. ‘The Delivery’ (Season Seven)

Only a couple of years after their marriage, Jim and Pam finally have kids. Pam’s pregnancy, however, is ripe for comedic potential. Having her stuck in the Dunder Mifflin office while in her final stages of pregnancy creates all kinds of chaos.

At stake is how Jim will keep his sanity in the office while Pam is on the verge of a water break. She finally gives birth to a daughter named Cecilia at the hospital. Pam is also trying to get the feel of breastfeeding, leading to some uproarious situations in nursing another baby in the same room.

Dwight Schrute factors into how this all ends. He was asked by Pam to go retrieve her iPod at her home. When Jim and Pam return home with Cecilia, they find Dwight building new cupboards for them because he found out the cupboard space had mold.

The Office is available to stream on Netflix and Hulu with Live TV.