The comedy show The Office follows the daily lives of the employees of Dunder Mifflin, a small paper business in Pennsylvania. While the overall show focuses on the careers and weekly hijinks the characters get up to, the main conflicts of each episode are driven by the relationships between characters and their various friendships, engagements, and marriages. Fans follow the relationships in The Office very closely, as the conflict between characters keeps the show fun and interesting.
Being a comedy, much of the relationship drama is played for laughs, such as Michael's constant love affairs and Phyllis blackmailing Angela to reveal her affair with Dwight. However, there are some genuinely heartbreaking moments in the series as fans connect to the characters and want to see them succeed.
Jim Moves To Stamford
Jim transfers to the Stamford branch after confessing his love to Pam and kissing her at casino night. Since Pam rejected him, Jim decides to accept the fresh start and soon begins a new friendship with Karen. However, Jim's move is hard on several people. Not only does Pam break off her engagement because of him but Michael also misses his friend and throws a tantrum the next time he sees Jim.
While Jim's move introduces the audience to brilliant characters, such as Karen and Andy, but is also heartbreaking because he and Pam clearly miss each other, and fans missed out on Jim and Pam's fun pranks.
Dwight Breaks Down In Front Of Jim
While Angela and Dwight weren't the center love story of The Office, they did have some sweet moments. However, that's not to say they didn't escape heartbreak either as season 4 can contest. Although it is clear that Angela and Dwight still care for one another despite their breakup, Dwight is devastated to hear that Angela has agreed to go on a date with Andy and ends up crying in the stairwell.
Despite their differences and rivalry, Jim comforts Dwight as best he can, relating Dwight's situation to his own. In a rare moment, Dwight reaches out to hug Jim without realizing Jim has already left. Dwight's love for the company and need to appear in control win over this time as he returns to his desk, but the subsequent episodes follow Dwight closely as he comes to with the break-up.
Jim Leaves Karen For Pam
Although they seem to be in a happy relationship, Karen suspects that Jim still loves Pam throughout her time at the Scranton branch. The most heartbreaking moment in their relationship is at the Christmas party when Karen finally asks Jim if he still has feelings for Pam, and he says yes. They continue dating, but Jim can't get over Pam, and they finally break up when they are both turned down for the management position in New York.
Karen and Jim's separation is sad because their relationship seemed fun and they joked around a lot, indicating that they really did like each other. Karen had some great moments on the show, such as teaming up with Pam to take down Angela's party planning committee, and losing her character was a harsh blow to the show.
Andy Finds Out About Angela's Cheating
Angela cheats on Andy with Dwight pretty much the whole time they are together, and Dwight and Andy end up fighting over her in the parking lot. In the end, they both break up with her, and Andy sadly cancels his wedding plans.
While the fight between the two men is funny, Andy seems genuinely sad that the breakup happened, and when he confronts Angela, his demeanor is serious and heartbroken rather than his usual peppy personality.
Holly Moves Back To Nashua
Michael's true love Holly is transferred from Scranton to Nashua after Dunder Mifflin's CFO David Wallace finds out about their relationship. Michael's road trip with Darryl and Holly to take her belongings to her new home is full of ups and downs and ends with Michael and Holly sadly separating instead of staying the night together as planned. Michael sings the blues with Darryl on the way home.
Michael's separation from Holly spurs the events of the Michael Scott Paper Company arc, since part of the reason Michael leaves Dunder Mifflin is that he wants to get back at them for forcing him to break up with Holly. However, despite winning that battle, it is still clear through several episodes that Michael is not over her.
Dwight Leaves After Andy Sabotages Him
Dwight loves Dunder Mifflin more than anyone and has no intentions of leaving. He even states in one episode that his dream is to die at his desk. However, Andy attempts to sabotage him by talking to Michael and playing into Michael's fears that Dwight will betray him again. Dwight's leaving speech is both hilarious and sad, and Angela's guilt makes the leaving even worse at it puts both characters completely out of their comfort zones.
Dwight leaving was never going to be a permanent move for the show, but it has a lasting effect on the other characters as Andy is sent to anger management, Jim its to missing Dwight, and Michael finally learns that Dwight is essential to the office.
Michael Mopes After Carol Leaves Him
Michael has always been a romantic, but this time he took it way too far, photoshopping himself into Carol's holiday photos. Carol dumps him and Michael mopes around the office, prompting Andy to take him to Benihana as a lunchtime treat.
Michael spends almost all of the episode moping around, as he thought that Carol was the one for him, but what makes this separation heartbreaking is Michael's genuine excitement at taking someone to Sandals, Jamaica, only to find himself alone when Carol breaks up with him. Michael returns to Jan at the end of the episode as a rebound.
Andy Does Not Invite Erin On His Boat Trip
Andy and Erin spent several seasons almost dating, and their nervousness at itting they like each other is both sweet and frustrating. When they finally get together, they seem to love spending time with each other, but Andy doesn't even think about asking Erin to accompany him when he takes his boat to the Caribbean.
Erin is frustrated at this and feels unappreciated, and this move also frustrated the audience since the build-up to their relationship had been so drawn-out, with both characters almost confessing their feelings and then not. Both Erin and Andy are bad at saying how they truly feel to each other, but in this case, it is heartbreaking to see their nerves actively getting in the way of their happiness.
Jim Pursues Athlead
Jim's move to Philadelphia to pursue a sports marketing job with Athlead was one of the more frustrating storylines the show pursued, and the move came with several heartbreaking moments, such as Jim missing Cece's ballet recital and Pam feeling lost and alone.
Jim ultimately decides to put his career goals on hold, making him much more sympathetic to the audience and ensuring that he and Pam would never feel lost again.
Pam Moves To New York
Pam finally pursues her dream of becoming an artist and moves to New York to attend the Pratt Institute's graphic design course. Unlike her first fiance Roy, Jim is ive of the move, but in multiple episodes, the couple finds it difficult to communicate long-distance and maintain their relationship.
In one of the best episodes of the series, Jim meets Pam halfway to New York and proposes to her, as the separation is getting to both of them and they realize they truly want to be together.