The Office might be a comedy, but romance is a back part of the series. There are so many different pairings that are explored throughout the series’ nine seasons, and some of these are much more central to the plot than others. However, even some of the relationships that don’t last very long end up being major catalysts for character development and change, such as Jim’s relationship with Karen.
The series has so many romantic couplings that ranking every single one would be tedious to read as even Michael’s girlfriends alone could make up a long list. So, for this article, we’ll look at the key relationships in the series and rank them based on how long they lasted.
Angela and Andy
Angela and Andy were never meant to be together, and everyone knew this from the start. Angela was only dating Andy as a way to get back at Dwight for killing her cat, Sprinkles. But, truthfully, Angela could never stand Andy to begin with. They had a horrible and unhealthy relationship, and Angela was cheating on Andy the entire time with Dwight, too. It’s no surprise these two weren’t together that long.
Jim and Karen
While Jim did have one another relationship on the show that was shorter, with the purse-seller Katy, his most notable relationship other than Pam was with Karen Filippelli. These two weren’t a bad match, and they did date for a good amount of time, all things considered. However, there are many other relationships from the series that last longer, and in the end, these two weren’t meant to be together because they were meant for others.
Erin and Andy
It’s hard to say exactly if Erin and Andy were really together for longer than Jim and Karen, but it does feel that way because this relationship plays out in various ways over many seasons. Erin and Andy start to have a ting for each other soon after Erin is hired, but their relationship is a mess. They are together only for Erin to get with Gabe for a while. Then, when they get back together again, the whole thing unravels when Andy goes off the deep end.
Michael and Jan
Michael and Jan’s relationship lasted for multiple seasons, but it’s worth pointing out that it was an on-again, off-again relationship. So, if you're counting break-ups, they often were together for all that long, but looking at the months and years they spent together, it adds up to be a lot. Micahel had many other short-lived relationships, such as with Carol and Donna, but his partnership with Jan was a big part of the show. It was a toxic coupling, and it's a good thing it didn't last forever.
Pam and Roy
Pam and Roy were actually together for a really long time, but we just don’t see them together for all that long in the actual series. It’s a fact that’s mentioned many times that they have been engaged for years, and they were dating before that, too. This relationship is a bad one, and Roy does many awful things to Pam. However, she struggles to find the confidence to leave him.
But, by season three of the series, Pam has left Roy and doesn’t marry him. She does briefly get back together with him, but thankfully, she comes to her senses again.
Oscar and Gil
Oscar and Gil are another couple that is together for quite a long time, but we just don’t see all that much of their relationship as Gil doesn’t work at Dunder Mifflin. We know that Osar is dating him for years and that they live together, so this is definitely a long-term relationship. However, Oscar does eventually break up with him and then starts dating Senator Lipton which is a short-lived disaster.
Ryan and Kelly
Ryan and Kelly have one of the most toxic relationships on The Office, but they still are together a lot. They also have a very on-again and off-again kind of relationship, but they are together at various times throughout most seasons. And, even after Kelly is with Ravi and Ryan has a son, they end up together again in the finale episode as Ryan does one of the worst things ever and just gives his son up to Nellie.
Angela and Dwight
While Angela and Dwight start out as a couple that no one was really rooting for as they were both awful, they started to grow on fans. Yes, they were both weird and horrible at times, but they were a strangely good match. They were together at various times, but they never really dated long-term for most of the series.
However, in season 9, they end up together and then get married in the last episode, so it appears as if they will be together for quite a long time and raise their son together, too.
Michael and Holly
While Michael and Holly meet in season four and date for a while, it doesn’t last long as Holly is transferred away to the Nashua branch. They don’t really see each other again until season seven when they start up their relationship. However, we know that this relationship lasts a long time as they get endgame and Michael moves to Colorado with her. Then, in the series finale, Michael shows up and is married to Holly, and they have children together.
Phyllis and Bob Vance
While Phyllis and Bob Vance might not be main characters as they are more of the ing cast, they do have a really long-lasting relationship. They get married before Jim and Pam, and they are together for the rest of the seasons after that. There’s no reason to assume that they don’t stay married for the rest of their lives making their union one of the most reliable on the show.