With its 201 often awkward, yet always hilarious episodes, The Office has likely made each of us laugh a thousand times over. Of course there have been many sitcoms that have kept us chuckling throughout their entire run, but very few of them were able to pull at our emotional heartstrings like The Office could. By setting the show within a typical workplace and filming it as if it were a documentary, the employees of Dunder Mifflin ended up touching us in ways that we never expected. (“That’s what she said.“)
It’s hard to believe that it’s been over three years since The Office has been off the air, and to deal with the heartache many of have resorted to making our way through the series all over again. And again. And possibly a third time, but who’s counting? You’d think by now we’d be emotionally prepared for the more sentimental scenes, but it turns out that the nostalgia only adds to our tears.
So here’s our look back at 15 Moments From The Office That Make Us Cry.
15. When Michael Gets Visited By Trick Or Treaters
Season 2, episode 5: “Halloween”
Despite loving them like a family, Michael Scott was rarely liked by his employees, especially in the first few seasons. This is particularly showcased when Michael is forced to fire one of his employees on Halloween, which leads to Michael being the only employee who is not invited out for drinks after work.
After cleaning the smashed pumpkin off of his car, Michael drives home to sit alone in his apartment. Seeing the characters out of the office setting was still a bit jarring this early in the show’s run, and seeing Michael’s home life was particularly depressing. But suddenly the doorbell rings and Michael is greeted by a number of kids in costume. Michael lights up and the day’s frustrations are totally washed away from him face. It’s this little scene that softens our hearts and reminds us that all Michael really wants is to connect with others.
14. When They Comfort Andy Backstage
Season 7, episode 3: “Andy’s Play”
Much like Michael at the beginning of the series, Andy Bernard was particularly annoying when he first appeared in season three. But four seasons later, the acappella-singing, sweater vest-wearing Cornell alum had finally started to grow on us.
Following his performance in Sweeney Todd, the employees of Dunder Mifflin meet Andy backstage only to find him experiencing a case of the post-show blues. His performance failed to win back Erin and he finally admits that the play was amateurish at best. Seeing his depressive state, and knowing what it’s like to be an under-appreciated performer more than anybody, Michael showers the aspiring thespian with compliments and the gang begs Andy to serenade them once more. With Darryl on piano, Andy treats us to a rendition of “I Try” that would make Macy Gray weep. But the fact that his co-workers were there to lift his spirits reminded us how much we’d come to appreciate Andy over the years.
13. When Erin Looks Up To Michael Like A Father Figure
Season 7, episode 8: “Viewing Party”
After being born four months prematurely and bouncing around foster homes thereafter, it’s no wonder that Erin has retained much of her childlike naivete. In this particular episode, Erin and Gabe host a Glee viewing party for their co-workers and Erin spends the night preoccupied with trying to get Michael’s to like Gabe. But as Michael puts it, “What is there to like? He’s just a weird little skeevy guy with no waist.” We couldn’t agree more, Michael.
He demands why Erin needs his approval in the first place, telling her that he’s not her father. This crushes Erin, and Michael has a moments of realization. He yells at Erin and tells her to go to her room as if she were a teenager. As the two continue to play along in their roles of father and daughter it becomes a sweet moment between someone who has always wanted to find her real parents, and someone who has always wanted to start a family.
12. When Jim Finds Out Pam Is Pregnant
Season 5, episode 28: “Company Picnic”
Plenty of sitcom couples get to live happily ever after in our minds once the show has ended, but not many of them get to actually start a family on screen. The news that Pam was going to have a baby came to a surprise to the couple as well as the audience in the season five finale.
After a minor injury during a volleyball game, Pam has to leave the company picnic and have her ankle looked at. Jim takes Pam to a nearby hospital while Dwight hilariously tries to stall the game until their star player can return. However, after Jim enters the examination room with Pam, the audiences’ care for who wins the game quickly dissipates.
This scene is beautifully captured without sound as the camera crew is kept outside of the room, but the shocked and then joyous expressions of the engaged couple tell us everything we need to know. When Jim steps out to make a phone call his eyes are even beginning to fill with tears at the news. Ours too Jim, ours too.
11. When Jim Comforts Dwight In The Stairwell
Season 4, episode 4: “Money”
After Dwight put Angela’s beloved cat Sprinkles out of its misery and into the freezer, Angela decides to give Andy – Dunder Mifflin’s second biggest dweeb – the opportunity to take her out to dinner. This wouldn’t have been so bad if Angela didn’t let these events unfold right in front of the already heartbroken Dwight.
Later, when Jim stumbles upon Dwight in the stairwell, Dwight has burrowed himself in the corner and is doing that eerie half-moan that is apparently as close as a Shrute ever gets to crying. Even though Dwight and Jim are office enemies, Jim finally admits why he left Scranton in the previous season. When Pam shot him down he couldn’t stand seeing her engaged to Roy. “Even food had lost its taste,” Jim tells Dwight. Anyone that’s been love-sick can relate, which is exactly what brings these two adversaries together in this scene which is sure to put a lump in your throat.
10. When Jim Cuts His Wedding Tie
Season 6, episode 5: “Niagara: Part 2”
After three seasons of dating, and with one bun in the oven, Jim and Pam finally tied the knot. But like any sitcom wedding, the ceremony was not without its blunders: Jim spilled the beans about Pam being pregnant, Andy tore his scrotum while dancing, and Pam ended up ripping her wedding veil moments before her walk down the isle. Jim attempts to console Pam, but when the typical compliments about her looks don’t do the trick, he grabs a pair of scissors and cuts his tie in half.
The couples takes control of their special day and flees the church. They get married on the Maid of the Mist below Niagara Falls before returning to the ceremony. It’s a beautiful moment when Jim shatters the expectations that weddings need to be an absolutely perfect event, and it’s sure to hit home with anyone who’s had to deal with wedding stress before.
9. When Michael Visits Dwight at Staples
Season 3, episode 13: “The Return”
After taking the fall for Angela, Dwight finds a new job working at Staples – one of Dunder Mifflin’s biggest competitors. But when Andy’s anger issues boil over at the office, Michael flees the scene to try to win back the company’s top salesman.
As Michael Scott tell us himself, it takes a big man to admit his mistake, and in this scene, Michael is that big man. After apologizing, Michael can’t help but ask Dwight to come back to work and Dwight is more than willing to oblige. After all, he’s not allowed to wear his ties and mustard colored suits at Staples.
Throughout the series, it’s always Dwight who’s busy seeking Michael’s approval, but here we’re reminded just how much Michael needs Dwight as well. It’s a tender moment between two stubborn man who are able to swallow their pride in order to save their friendship, and it’s sure to strike a chord in anyone that’s had to do the same.
8. When Michael Proposes To Holly
Season 7, episode 19: “Garage Sale”
For years it seemed like there would never be a woman that would be able to put up with Michael’s childish antics for more than a few episodes at a time. Enter Holly Flax. Though Holly and Michael originally got off on the wrong foot (Holly worked for HR after all), the audience quickly realizes that these two were made for each other.
After assembling his romance squad, consisting of Jim, Pam, Oscar, and Ryan, Michael decides to abandon his idea of using a look-alike corpse to propose to Holly, and he ends up popping the question right there in the office. After the dozens of candles set off the sprinkler system, Michael asks Holly to marry him by impersonating Yoda, and Holly says yes in an equally terrible accent.
7. When Dwight Is Hired As Manager
Season 9, episode 21: “Livin’ the Dream”
When Andy decides to leave his position as manager in order to pursue his lifelong dream of being famous, David Wallace is forced to hire a replacement. After gunning for the manager position since the beginning of time, all of Dwight’s perseverance and loyalty finally pays off if in the third to last episode of the series.
After getting awarded his black belt just earlier that day, this is a big episode for TV’s most beloved beet farmer, and when Wallace calls him into the conference room Dwight is dumfounded to the point that he can’t even blink. After being offered the position, Dwight falls to his knees and pays tribute to Wallace with what can only assume is some sort of medieval bow. Dwight pulls a business card from his wallet that already has his new title of “Manager” printed on it, reaffirming that he’s been waiting for the moment his entire life.
6. When Jim Confesses His Love For Pam
Season 2, episode 22: “Casino Night”
While his co-workers are busy gambling inside the warehouse during the company’s casino night, Jim lays all of his cards on the table when he finally tells Pam that he’s been in love with her all along. Unfortunately, after his 28 episodes of crushing hard on the office receptionist, Pam is unable to return the feeling. Despite being turned down, Jim gives it another shot and steals a kiss from Pam right before the episode ends, but it would be another season before his bold ultimately paid off.
Baring your heart to a close friend is no doubt one of the hardest moves to make, and we can’t help but feel for our favorite paper salesmen. This is definitely one of the most emotional scenes in the entire series, and we can’t help but wonder how many confessions this inspired out of people with real life office crushes.
5. When Jim Asks Pam Out On Their First Date
Season 3, episode 23: “The Job”
Pam was desperately trying to look on the bright side during the season three finale. She had broken things off with Roy for good, and with Jim on the verge of relocating to New York with Karen, Pam seemed content that they would simply remain friends. Even though the audience knew that that wasn’t how things were going to stay, this scene still caught us totally by surprise.
From the beginning of the show, it was understood that the conference room is where each character got to complete their daily interview without interruption. But when Pam is giving her confessional, Jim suddenly bursts in after driving straight back to Scranton from his interview in New York. He apologizes to the film crew and wastes no time asking Pam out on a date. Pam quickly agrees and when she turns back to the camera we can see her excitement starting to bubble up. And as her eyes begin to glaze over with tears of joy, ours can’t help but do the same.
4. When We Watched The Finale
Season 9, episode 23: “Finale”
Admittedly, the last few season of The Office were not its best. After Steve Carell left the show, no one else could ever fill the shoes of likable doofus Michael Scott, and there were episodes that seemed to lack the authenticity of the earlier seasons. But after living with these characters for nine years, it was impossible not to cry when The Office finally came to an end.
By making the documentary crew a part of the finale season we were treated to a nostalgia trip of all our favorite moments from seasons past. On top of that, Michael even made his return to fill in as “bestest mensch” at Dwight’s wedding. As the characters exit Dunder Mifflin together, it’s hard not to feel the same emotions as you would on the last day of high school or college. And Pam sums it up best when she tells us, “There’s a lot of beauty in ordinary things. Isn’t that kind of the point?” For nine years, The Office reminded us that if you look hard enough, ordinary lives can be a very beautiful thing.
3. When Jim Tells Pam She’s Everything
Season 9, episode 22: “A.A.R.M.”
It’s no surprise that Jim and Pam dominate this list. After all, they are one of the greatest sitcom couples of all time. So it makes sense that their most tearful moment for audiences takes place near the end of the show’s run.
Even though it was Jim who pined after Pam for all those years, it is ultimately Pam who starts to wonder if she’s enough for him. After Jim returns from his much more exciting job in Philadelphia, Pam can’t help but question if Jim is happy living with her in Scranton. With the help of the documentary crew, Jim puts together a video of all of the couple’s cutest moments from the past nine years. (And since we couldn’t fit every single P.B. and J moment on this list, this scene includes a bunch that we may have missed.) Once the video ends, Jim finally gifts Pam the letter he meant to give her years earlier, and reassures her that she’s everything he will ever need.
2. When Michael Leaves
Season 7, episode 22: “Goodbye, Michael”
In order to be with his one true love, Michael had to leave Scranton for Colorado. Because we loved Steve Carell’s performance so much, Michael’s departure was ultimately more bitter than sweet. However, the writers paid Michael a heartfelt farewell in one of the saddest episodes of the series.
As the episode approaches its end, Jim discovers that Michael’s last day isn’t tomorrow, and that he’s in fact leaving for the airport later that day. Like most people, Jim and Michael can’t stand goodbyes, so Jim agrees to tell Michael that when they go out to lunch tomorrow he’ll tell him how great of a boss he was – the best boss he’s ever had.
Pam even rushes to say goodbye to Michael at the airport. Once again, the scene is captured without being able to hear what the characters are saying, as they had to remove their mic packs to make it through the metal detectors. But their expressions alone are already enough to hit us right in the heart.
Honorable Mention: When Kevin Drops the Chili
Season 5, episode 26: “Casual Friday”
The Office has some of the funniest cold opens of all time. In fact, if you’ve just depressed yourself by reading this list, go watch the opening of “Stress Relief: Part 1” where Dwight sets a fake fire in the office so his co-workers start taking his safety training more seriously.
However, not every cold open is filled with laughs, and this particular episode begins with the lovable-loaf Kevin entering the office bright and early with a huge pot of homemade chili. As his voiceover tells us, the recipe takes him hours to make, and it’s probably the thing he does best. But as Kevin should know, one out of order elevator plus one overweight man carrying a heavy pot of chili does not add up – he is an accountant after all. And before Kevin can make it to the break room, he drops the chili. Kevin desperately tries to salvage what’s been lost, but it’s too late. They say there’s no use in crying over spilled milk, but spilled chili is a totally different story.
1. When Michael Shows Up At Pam’s Art Show
Season 3, episode 16: “Business School”
With Jim happily dating Karen, our favorite receptionist was at an all time low in this episode. What’s even worse is that none of her co-workers showed up to her art show (aside from Oscar and his partner Gil, who end up calling her paintings “motel art”).
Just as Pam begins to take down her artworks, Michael suddenly rushes in and apologizes for being late. In his child-like sense of wonder, Michael can’t believe that Pam has created such realistic paintings, and gives her his highest compliment when he says, “My God, these could be tracings.” But there’s one painting that Michael can’t look away from – their office building. He insists on buying it, and the down-on-her-luck Pam can’t believe it. She embraces Michael, a boss who she usually can’t stand.
And it’s these little moments that The Office is filled with that serve to remind us how big of an impact we actually have on the people in our lives.
So what scenes from The Office turn you into a puddle of tears? Let us know in the comments.
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