Jim is, at the end of the day, a sensitive soul. Sure, he puts on a funny act as the careless prankster of The Office, yet when it comes down to it, this is one emotional dude. He feels for the people around him, appreciating all of the quirky relationships he has developed with the people of Dunder Mifflin over the years.
His sentimental ways lead for a lot of tear-jerker moments throughout the series that never seem to leave a single dry eye. What were some of these heartbreaking moments with Jim? Read on to find out!
WHEN JIM SAID GOODBYE TO MICHAEL
When Michael and Holly decide to move to Colorado in order to start a brand new life as a married couple, it is time for everyone in the office to say their emotional goodbyes. Perhaps the saddest goodbye of all comes from Jim as he confesses to Michael that he is "the best boss" he has ever had.
Both are tearing up, and Jim gives one last look t0 the camera the way he usually does whenever Michael says something obnoxious. But this time instead of looking flustered, he reveals a genuine smile. At the same time, he is brimming with tears.
WHEN JIM & DWIGHT DISCUSS THEIR LOVE LIVES
Although Jim and Dwight are known to be sworn enemies throughout the series, Jim can't help but empathize with the beet farmer extraordinaire in a particularly heartbreaking scenario. Dwight overhears the love of his life Angela accepting a date with Andy. He goes to the stairwell to cry over it, and Jim rushes out to comfort him.
He's been there, as he tells Dwight the whole ordeal when Pam was with Roy. He then tells Dwight he wouldn't wish that terrible feeling on his worst enemy. Dwight then tries to awkwardly reach out to hug Jim, but at that point, Jim is long gone.
WHEN HE FINALLY CONFESSES HIS LOVE FOR PAM
Perhaps one of the most essential moments on the history of The Office is when Jim finally lets his guard down and confesses his feelings for Pam. The two have been heavily flirting for the entire series with tension so strong between them, it's nearly impossible not to get all the feels. So finally when Jim decides he can no longer hold in his feelings, all hell breaks loose.
Pam is terrified to actually feel something that is real and leave Roy, her high school sweetheart. It is all just too overwhelming, so she tells Jim she loves him as a friend, even though we know this not to be the case. It's a real challenge to watch this scene without shedding at least one tear!
WHEN JIM GETS MICHAEL TO BE DWIGHT'S BEST MAN
When Dwight and Angela get married, Jim decides to pull the "best prank ever" on Dwight by getting Michael Scott to come back to Scranton after a whole season hiatus. He arranges it so Michael can be Dwight's best man rather than Jim because Jim understands the true and pure connection between Dwight and Michael.
The bond between the two is so genuine, innocent, and everlasting, that it is almost impossible not to break your heart to pieces with the knowledge that the series is coming to an end. Seeing Michael Scott standing there usually induces loud screams of surprise from viewers, followed by heavy tears. We're not crying, you're crying!
WHEN JIM HUGS PAM AMIDST THEIR STRUGGLES
In season 9, fans of The Office become utterly shocked to discover turmoil in Jim and Pam's supposed "fairytale relationship." Some people loathed this plotline, finding it unnecessary and out of character, especially on Jim's end. Other people really appreciated the struggles unleashed upon Jim and Pam's relationship, considering their issues to be an honest depiction of real-life relationships.
As Jim and Pam get into heartbreaking situations that nearly break them as a couple, Jim suddenly realizes how much he has been taking Pam for granted and he gives her the most earnest hug, indicating his love for her.
THAT AWFUL PHONE CONVERSATION BETWEEN JIM & PAM
To continue on with Jim and Pam's relationship turmoil, one of the hardest scenes to watch was witnessing the near downfall of their marriage. Their relationship had been on the rocks because Jim decided to pick up a new job at a startup company in Philly, while Pam was left in Scranton trying to make things seem perfect for their daughter.
The near-breaking point occurs as Jim and Pam have a phone conversation that results in Jim cursing Pam out for not properly recording Cece's dance recital. It's as though all the beauty and love between Jim and Pam had been ripped apart because of Jim's selfish behavior. So basically, it caused fans to casually give up on the idea of love once and for all.
JIM'S SECRET SANTA GIFT
It takes a lot for something to be heartwarming and heartbreaking all at once, but The Office always manages to pull it off with ease. This is especially true when Jim puts in an adorable amount of effort for Pam's Secret Santa gift. He makes it personal because that's what you do when you truly love someone.
Jim gives Pam a teapot that is filled with memorabilia representing all of their inside jokes, including a high school picture of Jim that Pam loves, hot sauce that she had mistaken for ketchup, and a note expressing his true feelings for Pam. Of course, what made the moment so sad was when he snatched the note away from Pam when she wasn't looking, deciding it wasn't right to tell her how he felt. Poor Jim!
YOU LOOK LIKE YOU NEED TO TELL ME SOMETHING
In this scene from season 2, Jim and Pam are sitting together near the vending machines, and Jim isn't allowed to talk because he has been jinxed. The two of them are gazing at each other with that look of affection that can only be reserved for your one true love. Pam tells Jim that he looks like he needs to tell her something and that he can tell her anything.
Then you see the look on his face after she says that, knowing Pam is the love of his life despite the fact that he can never be with her because she is engaged to someone else. This scene makes us want to give Jim a big old hug!
WHEN JIM MAKES THE VIDEO FOR PAM
Pam is starting to worry about Jim's feelings for her. She is getting more and more insecure that Jim isn't happy with the life he has with her. She also assumes that Jim is having regrets when it comes to choosing her as the love of his life. But, as we discover from the video Jim made for her, this is the opposite of how he truly feels.
He asks the people making their documentary about Scranton to compile a bunch of clips revolving around the evolution of Jim and Pam's love life. It is too beautiful for words, and if you don't cry during the video montage, there is a good chance you don't have a soul.
NOT ENOUGH FOR ME? YOU ARE EVERYTHING
Jim finally gives Pam the letter that he wrote to her from his Secret Santa gift, the one he planned to give her years ago. In that one moment, all of Pam's feelings of doubt and insecurity in regards to how Jim feels about her have washed away.
Pam is Jim's everything. She has always been Jim's "Plan A," and being with her has made him into the happiest man on earth. Despite the difficulties that the two experienced in season 9, they were finally able to move past their hurdles and grow even stronger as a result.
Which moment made you cry the hardest?