For fans of The Office, it’s no surprise that the relationships are a big part of the show. While the comedic elements might be the biggest draw, fans also got attached to the characters and watching their lives develop, and there were a lot of different romances on the show.
While Jim and Pam might be the most beloved, there were other couples that would have been great together that fans were rooting for but that never happened. There were also many disappointing relationships that fans wish hadn’t been made canon on the show.
Wish Had: Karen Fillipelli and Jim Halpert
While some fans wouldn’t ever want Jim to be with someone else besides Pam, the truth is that Karen and Jim would have made a great match. if Jim would have been able to get over Pam, they probably would have actually been a better match.
This is because Karen and Jim were more evenly matched as far as personalities and ambition. They were both more motivated people, and they would have challenged each other more. Karen was also more independent and had her own thing going on which is really helpful.
Wish Hadn’t: Andy Bernard and Erin Hannon
Erin was a character who was basically given a narrative arc with many different men over the series. It seemed like the creators of the show never really knew what to do with Erin as a character, so they just tried out different romances to see if they worked.
While Andy and Erin seemed all right at first, Andy continually got worse and to be more of a jerk. In the end, it was clear they wouldn’t be good together, and it had just been a poorly executed storyline.
Wish Had: Pam Beesly and Brian
While not all fans were on board with this, there’s no denying that Jim and Pam had a pretty bad relationship during the final season. Brian did seem to actually care about Pam, and he seems more in tune with her realities and what she was going through. Jim could honestly be really selfish at times, and their relationship isn’t perfect.
While Jim and Pam did work it out, in another reality, Pam and Brian could have worked out well.
Wish Hadn’t: Oscar Martinez and Robert Lipton
One of the more unfortunate storylines in The Office is Oscar having an affair with Angela’s husband. It made Oscar seem like a bad guy, and it wasn’t a very good LGBT representation.
Given that the series never really had a positive LGBT couple featured for more than a moment or two, it was kind of disappointing that this is the only longer story arc with LGBT themes. Oscar definitely deserves to have a better romance than this one.
Wish Had: Michael Scott and Ryan Howard
This might be one of the less obvious relationships on the list, but the truth is that it would have been interesting. This wouldn’t have been a couple that would last for a long time by any means as Ryan is an awful and selfish person, but there were definite undertones of Michael being attracted to Ryan.
It would have been an interesting storyline to explore as a fling even if they wouldn’t have actually been good together.
Wish Hadn’t: Erin Hannon and Gabe Lewis
While Erin and Andy might have been a bad couple, Erin and Gabe were even worse together. It was clear that Erin never wanted to be with Gabe but just didn’t know how to turn him down.
She didn’t even like him as much as he liked her, and he never really listened to her or respected her. Their relationship was uncomfortable, and it was strange writing to have Andy and Erin suddenly not be together and have Erin be with Gabe instead.
Wish Had: Daryl Philbin and Val
This is a couple that actually did get together for a brief moment, but for some reason, it was written off in a bad way. Daryl had been really interested in Val, but then after they got together he broke up with her for no good reason. She was clearly a great catch, and they would have been a great match.
It’s strange that The Office didn’t allow these two to actually be a couple as they could have been interesting and good together.
Wish Hadn’t: Toby Flenderson and Nellie Bertram
Of all of the awkward and uncomfortable relationships from the series, Toby and Nellie’s was the most uncomfortable. While Toby had always been shy and awkward at times, he seemed like some sort of predator or pervert in this short-lived relationship.
He clearly made Nellie uncomfortable but wasn’t aware of it, and it was just really cringy to watch the entire way through.
Wish Had: Oscar Martinez and Matt
Matt was another warehouse worker that Oscar briefly had a crush on. While this never went anymore, it would have been a great relationship to explore. Oscar was with Gil for a while, but we never really saw that relationship.
Seeing Oscar in a happy, healthy relationship and how that developed over the series would have been a great move on the show’s part. But, instead, this didn’t happen at all and Oscar just ended up having his affairs with the Senator instead.
Wish Hadn’t: Michael Scott and Helene Beesly
Michael Scott had a lot of awful relationships during the nine seasons, but one of the hardest to watch was his relationship with Helene, Pam’s mother. While Michael’s relationship with Jan might have been the worst, the one that really came out of nowhere was Helene.
Then, the fact that he broke up with her on his birthday, in front of Pam, and was so obtuse about her age was really uncomfortable.
