“Sometimes, I’ll start a sentence and I don’t even know where it’s going. I just hope I find it along the way.”
Well said, Michael Scott. That’s the perfect way to introduce For The Win’s tribute to The Office, the NBC comedy that celebrates the 15th anniversary of its premiere this week (March 24). For the show that’s still so embedded in American and internet culture, we’ll break down everything from the best sports moments to the best couples. Because, as Wayne Gretzky Michael Scott says, “You miss 100 percent of the shots you don’t take.”
When we made a list of couples from The Office, we quickly realized how ridiculously incestuous that workplace is (although it’s pretty standard for long-running sitcoms). The list ranged from obvious contenders for the show’s best to ones we totally forgot about and are, therefore, pretty insignificant.
So we narrowed it down to the top-10 couples. This isn’t about the best or healthiest relationships or which ones are #RelationshipGoals. These are our favorite couples to watch, from the heartwarming to the totally dysfunctional and everything in between.
10. Oscar and The Senator
Oscar’s affair with Angela’s husband, the senator, adds some needed depth to his character. But it also, weirdly and unexpectedly, brings Oscar closer to Angela when they realize they’re both in a relationship with (and political props for) a terrible person who’s using them. But throughout, you know this relationship is going to end in catastrophe eventually, and catastrophic couples are fun to watch. So you couldn’t help but want to know what would happen here. And while both Oscar and Angela get hurt, they also become actual friends because of it, which is kind of sweet. — Michelle Martinelli
9. Jim and Karen
Jim and Karen were a good, not great, match. With solid chemistry, they had fun and seemed similarly ambitious about their futures. But Jim was never fully invested in Karen because he was still in love with Pam, and you knew that relationship was never going to work out. Jim and Pam were the primary will-they-or-won’t-they relationship in the beginning, and Karen just served as obstacle in that storyline that you weren’t really invested in. — MM
8. Andy and Angela
Look at it this way: we needed Andy and Angela to “date” while she had an illicit affair with Dwight (which packed so much comedic punch), who she would end up marrying. There’s value in that! There’s also value in “The Duel,” in which Dwight and Andy fight for her affections. — Charles Curtis
7. Darryl and Kelly
What a hilarious, twisted mess. Kelly is initially only with Darryl — and flaunts it to a ridiculous extent — to make Ryan jealous, so you might normally feel bad for him. But his total indifference to Kelly is comical, especially when she cranks up the intensity any time Ryan is around. And when she breaks up with Darryl for Ryan, his response is perfect: “It’s cool.” — MM
6. Phyllis and Bob Vance, Vance Refrigeration
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Note that we had to use Bob Vance, Vance Refrigeration’s full name.
Anyway! Their love is pure and simple, with ZERO drama, and their wedding was so good although even if it borrowed liberally from what was supposed to be the nuptials between Pam and Roy. — CC
5. Michael and Holly
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Michael got his heart broken multiple times, and suffered through Jan, but eventually found his soulmate. Holly is Michael’s perfect match in every way, and although their exceptionally dorky personalities can lead to some cringeworthy moments, it’s endearing to know that Michael ends up with his perfect match, which is eventually confirmed years later in the series finale. You’ve gotta love these two together. — MM
4. Michael and Jan
Okay, look. It was a disaster of a relationship, an absolute trainwreck. BUT! It was fascinating to watch Jan convince herself that it was something she wanted, amazing to see Michael as a romantic figure … and then you got to watch it crash and burn spectacularly. On top of that, it gave Michael a chance to see that Jan wasn’t right for him. — CC
3. Jim and Pam
So, here’s the thing about Jim and Pam. The will-they-or-won’t-they arc is fantastic, and Jim finally asking Pam out while she’s talking to the camera is one of the most perfectly crafted scenes. They’re funny and goofy and make a great team while pranking Dwight. But once they get together and have a baby, they become kind of bland and just sort of exist as a couple on the show. An easy fix to that would have been significant marriage problems earlier than the final season. They’re still great, but they’re not the best. — MM
Jim and Pam are in the pantheon of all-time sitcom couples. I want them SO BADLY to be higher up, because even in those “bland” years — as Michelle put it above — we saw them struggle in a very real way. It wasn’t just sunshine and rainbows for the couple that got engaged in the rain. But I get it. There are probably better couples. Sigh. — CC
2. Kelly and Ryan
Kelly and Ryan are an absolute disaster from the beginning — when Ryan instantly regrets hooking up with her on February 13 — to the very end when Ryan abandons his baby and Kelly leaves her husband so they can run off together. And their relationship creates some of the best scenes, one-liners and, subsequently, GIFs. They’re horrible, selfish, shallow and hilarious characters who are perfect for each other, creating a toxic, dumpster fire of a relationship we can’t get enough of. And, most importantly, they deserve each other and got an ending fit for two poisonous people, and I love them for it. — MM
1. Dwight and Angela
Their roller coaster was the wildest of them all. They kept their early relationship a secret. They had a breakup after Dwight killed her cat. They had an affair in the warehouse while Angela is dating Andy. They end up having a baby together before she marries a state senator. And the series ends not with any of the other couples getting married, but these two, when we could finally see them truly expressing their feelings about each other in public, with no walls between them.
Read that whole thing over and tell me that’s not a romantic comedy you’d watch over and over. That’s why they’re No. 1 — CC
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