The Office: Every Couple, Ranked From Worst To Best

When the American version of the sitcom The Office went off the air in 2013, it left quite a legacy — and part of that legacy was its impressive roster of relationships. Some of those relationships were awful, some were aspirational, some were short-lived, and some stood the test of time. One way or another, over nine seasons it became clear that the seemingly mundane offices of Dunder Mifflin, a paper company in Scranton, Pennsylvania, were actually quite a hot bed for romance.

In fact, Dunder Mifflin may hold the record for the most relationships between co-workers in a single small office. While characters occasionally left the office to seek out a significant other, an astonishing number of employees found just what they were looking for in the place they worked every day.

Of course, this was sitcom-land, and in sitcom-land characters are intimately tied together regardless of the situation the show depicts. The Office’s approach kept with this tradition. Fans were invested in the show’s characters and when two of them got together their investment became even greater, whether they were cheering a couple on (Jim & Pam!!!) or cringing in disbelief (Michael & Jan). Fans wanted their favorite characters to find a romance that worked for them, no matter how quirky they were, and when it happened it was a beautiful thing. Many of The Office‘s characters endured relationship highs and lows, both hilarious and heartbreaking, along the rocky road to romance. By the end of the series, several characters had even achieved the happiness fans wished for them.

Here we review everyThe Office Couple, Ranked From Worst To Best.

25 TOBY FLENDERSON & NELLIE BERTRAM

Toby Flenderson was the Dunder Mifflin punching bag throughout The Office and therefore seemed destined for minimal success in love. Yet, when Nellie showed up dressed as him for Halloween, Toby found himself oddly attracted to her.

Things progressed when Nellie shows interest in hearing about Toby’s time on the jury of the Scranton Strangler case, becomes bored with his yammering, and kisses him to get him to be quiet. Toby mistakes the smooch for much more than it was, however, and acts as though they’re together, despite every sign from Nellie that they’re not. This coupling was uncomfortable and wrong, making viewers hate Toby just as much as Michael Scott did.

24 MICHAEL SCOTT & HELENE BEESLY

In one of the more inexplicable storylines on the series, Michael meets Pam’s mom, Helene, at Jim and Pam’s wedding and starts to date her. When Pam finds out she’s inevitably horrified.

Against their better judgment, Jim and Pam agree to go out to lunch with the new couple when Helene comes to the office for her birthday. Pam starts to warm up to the relationship when he sees how well Michael treats her mother. However, after Michael discovers Helene is 58 years old and realizes she’s about to be a grandma, he breaks up with her, angering Pam all over again. From start to finish this relationship was a showcase for Michael’s worst impulses.

23 ANGELA MARTIN & ROBERT LIPTON

Angela Martin married Robert Lipton after the collapse of her relationship with Dwight. She was impressed with his role as a Senator. Unfortunately, she was also completely oblivious to the fact that he was in the closet and cheating on her with her co-worker Oscar and probably several other men.

Angela tried to be a good political wife and stand by her man, but it led to far more humiliation than she could ever have anticipated. When the Senator asks Angela to participate in a press conference in which he confesses that his marriage to her helped him realize that he doesn’t like women, his public coming out ends up being far smoother for him than for her.

22 MICHAEL SCOTT & JAN LEVINSON

Michael and Jan’s relationship was perhaps the most toxic of the many relationships on The Office. Initially the pair didn’t even like each other. She was the critical boss from corporate, he was the wasteful manager of an underperforming branch. Yet, after watching him land a client while downing margaritas, Jan brings him to her hotel.

Even though they still didn’t appear to like each other that much, Michael and Jan ended up going to Jamaica together. After that they made their relationship official. Despite being on and off again, they moved in together after Jan was fired from Dunder Mifflin. Three vasectomies and one cringe-inducing dinner party later, the pair finally ended things. Yet, Jan still managed to pop up from time to time to remind everyone of the horror that was this relationship.

21 OSCAR MARTINEZ & ROBERT LIPTON

Oscar Martinez was the lone gay man at the Scranton branch of Dunder Mifflin. Unfortunately, he didn’t have the most interesting dating life in the office. His most noteworthy relationship was this coupling with Senator Robert Lipton, Angela’s husband.

While Oscar did what he could to keep the Senator’s infidelity from Angela, the truth eventually came out. Both Oscar and Angela stayed with the Senator, however. Oscar even excused the Senator’s behavior when he had Oscar come to a campaign event because he needed a token Latino. The Senator eventually broke it off with Angela and Oscar, instead choosing to be with the man he really loved — his campaign manager. Despite the situation, Oscar and Angela stayed friends, and Oscar even became godfather to Angela’s son.

20 DWIGHT SCHRUTE & ESTHER BRUEGGER

In many ways, Esther was the perfect match for Dwight. She lived on an adjacent farm and understood the customs that were a part of Pennsylvania farm life. Plus, they were third cousins, which Dwight points out is great for bloodlines (yay!). Esther was also genuinely into Dwight, showing up to support him whether he was earning his black belt or attempting to win a paper airplane contest.

Things go so well in their relationship that Dwight brings a ring to the office, invites Esther for lunch, and almost proposes. Ultimately, though, Esther was never the right one for Dwight. Fans knew he was destined to be with Angela all along. So when his feelings for Angela prevent him from proposing to Esther, fans weren’t surprised when he proposes to Angela instead.

19 ROY ANDERSON & PAM BEESLY

When The Office began, Pam was engaged to her high school sweetheart, Roy. In fact, they’d been engaged for three years and had yet to set a date for the wedding. Roy worked in the Dunder Mifflin warehouse so he was around all the time. Despite his constant presence, he was insensitive and unsupportive of Pam, with seemingly minimal awareness of anything that was going on in her life.

Pam finally sees the light and breaks up with him just before they were finally supposed to get married. Roy manages to briefly win her back. However, when he goes on a rampage after Pam admits she kissed Jim, she promptly breaks up with him for the second time. Thankfully this time it was for good.

18 MICHAEL SCOTT & DONNA NEWTON

Michael met bar manager Donna when she tried to kick him out of her establishment for his bad behavior. He refused to go and then confronted her for embarrassing him in front of his friends. At some point, their conversation turned from an argument to a flirtation, with Donna clearly showing an interest in Michael.

The pair ends up kissing when Donna comes to the Dunder Mifflin offices supposedly to buy office supplies. They seem to be really enjoying the relationship until Michael starts to suspect Donna is being unfaithful. He learns things aren’t quite as they seem though — Donna is married, making him the “mistress” in the situation. Michael tries to justify staying with her, but ends up breaking things off with Donna via text.

17 GABE LEWIS & ERIN HANNON

Erin started dating Gabe the summer after she and Andy broke up. While Erin seemed excited about the new relationship at first, she soon started to eat lunch in her car just to get away from Gabe. Pam finally convinces Erin to break up with him, which she does to the shock of Gabe and the rest of their co-workers by announcing that she is not attracted to him while accepting a Dundie Award.

Gabe handles the break up poorly and attempts to get Erin back. Erin decides she needs to be alone, though, which seemed totally appropriate. Gabe was never a fan-favorite character, so it was hard not to root for Erin to get away from him and find someone better.

16 ANGELA MARTIN & ANDY BERNARD

When Andy transferred to the Scranton branch of Dunder Mifflin he found himself attracted to Angela. She didn’t return his affections, but he was determined to win her over anyway. After serenading her and gifting her a cat, Angela finally agrees to let him take her to dinner. Eventually, they got engaged, but Dwight and Angela resumed their relationship the night Andy proposed.

Andy dove into wedding planning, but despite some half-hearted attempts to stay faithful, Angela continues her relationship with Dwight. Once Andy discovers the affair, Angela loses both Andy and Dwight. However, she eventually gets back together with Dwight, the man she should have been with all along.

15 RYAN HOWARD & KELLY KAPOOR

Kelly was vapid and selfish, Ryan was arrogant and self-centered. And although their relationship was a mess from start to finish, they were kind of made for each other. Ryan habitually was not a good boyfriend, Kelly dated other people just to make him jealous, and they broke up and got back together regularly.

Ultimately the couple couldn’t seem to get away from each other. So, when Kelly moved to Ohio with her fiancée, Ravi, Ryan followed. Then, when they reunited at Dwight and Angela’s wedding, Ryan gave his baby strawberries to prompt an allergic reaction just so he could have some alone time with Kelly. They ultimately ended up running off into the sunset together – although how long that lasted is anyone’s guess.

14 JIM HALPERT & KATY MOORE

Before Amy Adams was known as an Oscar-nominated actor, she guest-starred on The Office as Katy. When Katy showed up at Dunder Mifflin hoping to sell purses there, she quickly attracted the eye of several of the employees, including Dwight and Michael, who dubbed her Pam 6.0. Although Jim claimed Katy wasn’t his type, by the end of the day he had successfully asked her out.

This led to a brief relationship that ended after they watched Roy and Pam set a date for their wedding, a move that seemed to prevent Jim from finally declaring his feelings to Pam. Jim told Katy they would never have what Roy and Pam have and broke up with a shocked and angry Katy.

13 ANDY BERNARD & ERIN HANNON

Andy and Erin took a long time to get together. After making all sorts of awkward attempts at flirting with an oblivious Erin, Andy finally successfully asked her out. In many ways, this pair was well-suited for each other, and they had a cute chemistry that was fun to watch.

After breaking up and getting together with other people, they developed a friendship and eventually rekindled their romance. Things went south, though, when Andy took off on a boat trip to the Caribbean with his brother. Erin is disappointed that he never considered inviting her along but tries to be supportive anyway. After the trip extends to three months, though, and Andy barely emails her while he’s away, Erin becomes increasingly upset by his irresponsible behavior and finally dumps him when he returns.

12 KEVIN MALONE & STACY

When it came to marriage proposals, the fourth time was the charm for Kevin. While the first three women turned him down, Stacy ended up being lucky number four. The few times she’s seen on The Office, Stacy comes across as an unassuming presence, but when Kevin talks about her, their relationship sounds stranger.

Kevin and Stacy were engaged for a long time and he even takes Stacy’s daughter to the office on Take Your Daughter to Work Day. When his co-workers asked if the couple set a date, Kevin gets defensive and tells them it’s “complicated” and eventually the two break up. Kevin says the end of their relationship was tough — Stacy left him after he comments that he thinks the Eagles could win the NFC East.

11 MICHAEL SCOTT & CAROL

While Michael did several questionable things in his relationship with Carol, she was still a pretty solid choice. Carol, played by Steve Carell’s real-life wife, Nancy Walls, was the realtor who sold Michael his condo. He asked her out even though he believed he was also going out with Jan at the time.

Michael and Carol’s relationship progressed fairly well until for some reason Michael decided to propose after only a few dates. The last straw for Carol came when Michael photoshopped his head onto her ex-husband’s body in a photo from a ski trip Carol took with him and their kids and sent it out as a Christmas card. Carol simply had no idea how to deal with Michael’s shenanigans, especially since he didn’t seem to comprehend what the problem was.

10 DARRYL PHILBIN & KELLY KAPOOR

Kelly got together with Darryl during one of her many breakups with Ryan. Darryl seemed like the perfect antidote to Ryan. He wasn’t willing to put up with her antics and refused to play her games. It was such a unique experience for Kelly that she found it confusing, but in a good way.

Nonetheless, Kelly was still stuck on Ryan and was mostly using Darryl to make him jealous. Kelly’s ploy was so obvious that Darryl confessed that he would get excited when he saw Ryan coming. Clearly, this couple wasn’t going to go the distance, so when Kelly broke up with Darryl over text message, fans — and Darryl — weren’t remotely surprised.

9 KELLY KAPOOR & RAVI

Pam was responsible for setting Kelly up with Ravi, her children’s pediatrician. Ravi was a vast improvement over Ryan, and he clearly adored Kelly. Their relationship made Ryan jealous though, and he did his best to break them up and win Kelly back. After a grand gesture, it seemed like Ryan may have succeeded.

Ultimately, Kelly made the right choice and stayed with Ravi. They got engaged and she even moved to Ohio with him when he got a job at Miami University. Of course, part of her decision to go with him may have been due to the fact that she thought they were moving to Miami, Florida, but at least she stayed with him after learning the reality. That is, until Ryan showed up at Angela and Dwight’s wedding and Kelly finds she isn’t able to resist him after all.

8 OSCAR MARTINEZ & GIL

Oscar was with Gil before the rest of the office learned about his sexuality. While Dwight was the first to meet him and Gil and Oscar were clearly affectionate towards one another, Dwight was oblivious. Once Michael outed Oscar to the Dunder Mifflin employees, Gil remained scarce. Oscar almost brought him to the Christmas party but left at the last minute. They attended Pam’s art show together, but Gil was dismissive of Pam’s work, calling it “motel art.”

Despite all that, Oscar and Gil appeared to have a pretty steady relationship. Oscar eventually broke up with Gil, but it seemed like a low-key and respectful relationship while it lasted, and after a while, Oscar implied that he missed it.

7 DARRYL PHILBIN & VAL

When Val joined the warehouse crew, Darryl was immediately attracted to her. Unfortunately, she was already in a relationship and didn’t return his interest. At least at first. However, when Darryl stood up to her jealous boyfriend, Val seemed to change her tune and the pair finally got together

Their relationship was ultimately short-lived, but the two had a fun dynamic that had fans rooting for them. Eventually, though, Darryl convinces himself that the relationship is a dead end and he needs his freedom because he’s planning to pursue a job in Philadelphia. In the series finale fans learned that Darryl ended up moving even farther away, to Austin.

6 JIM HALPERT & KAREN FILIPPELLI

After declaring his feelings to Pam and being rejected, Jim transferred to Dunder Mifflin’s Stamford branch where he met Karen. Karen was smart and clever and could banter with the best of them. She represented a new chance for Jim to pursue a positive relationship. If Pam wasn’t in the picture, these two could’ve made it work.

However, once the Stamford branch shut down and Jim and Karen transferred to Scranton, Jim’s feelings for Pam roared back to the surface. Jim tried to stay faithful to Karen, but his desire to be with Pam becomes undeniable after she announces he was the reason she broke off her engagement. Jim ended things with a devastated Karen soon afterward.

5 PETE MILLER & ERIN HANNON

Pete was Erin’s third office romance but this time it seemed like it might be built to last. Erin started bonding with Pete while she was still with Andy. At that point in their relationship, however, Andy had become selfish and oblivious. When Andy took off for an extended boat trip with his brother, a disappointed and frustrated Erin, quickly noticed how attentive and caring Pete could be.

While they started things slowly and Erin almost didn’t go ahead with her plan to break up with Andy, their first kiss gave her the courage to let Andy down and move on. The couple seemed to be making it work, as they were still together at Dwight and Angela’s wedding a year later.

4 ANGELA MARTIN & DWIGHT SCHRUTE

Throughout The Office, Angela and Dwight had several secret dalliances. While they wanted to keep their relationship under the radar, they genuinely seemed to care for each other. However, something always broke them up. First Dwight eliminated Angela’s cat, then Angela got engaged to Andy. Finally, they agreed to have a baby together but Angela ended up marrying the Senator instead.

Although Angela has a baby that was clearly conceived before her marriage, she refuses to acknowledge Dwight’s paternity until after her relationship with the Senator ends. Fortunately by that point both she and Dwight have realized their feelings for one another. It’s hard to say why these two work but they do. They share a similar appreciation for rules and accept each other’s foibles, so it seemed right when the series ended with their wedding.

3 PHYLLIS LUPIN & BOB VANCE

While fans of The Office tend to focus on the magic of Jim and Pam, the person who was in the longest and healthiest romance was actually Phyllis — and with someone outside Dunder Mifflin. Of course, Phyllis didn’t go far to find her man, Bob Vance of Vance Refrigeration, another business with offices in the same office park.

Phyllis and Bob were adorable together and sincerely loved each other. He was protective of her and showered her with gifts. Plus, despite being married in season 3, they maintained a passion for one another throughout the series. Sometimes this led to uncomfortable disclosures from Phyllis, but it was also nice to see her continue to celebrate her amazing marriage.

2 MICHAEL SCOTT & HOLLY FLAX

By the time Michael met Holly his track record when it came to relationships was not good. Yet when Holly walked into his office for the first time, they made an instant connection. Michael was shocked to realize he might actually like someone who works in HR, as his spark with Holly quickly turned into a flame.

While the pair broke up when she is transferred to Dunder Mifflin’s Nashua branch, Michael never really gets over her and they quickly rekindle their romance when she comes back to Scranton. Michael makes the decision to propose and follow Holly to Colorado to help her with her aging parents. This couple shared a common sensibility and quirky sense of humor that gave them a solid foundation. In the series finale, it’s revealed that Michael and Holly are happily married with children.

1 JIM HALPERT & PAM BEESLY

Jim and Pam’s place at the top of this list should come as no surprise to fans of The Office. From the start of the series, Jim and Pam had something special. Even though it took them way too long to admit their feelings for one another, fans knew it would happen sooner or later.

While sitcoms like Friends maintain the will-they/won’t-they tension of romances between lead characters for most of the series, Pam and Jim got together for good by Season 4. By season 6 they were married with children and fans even saw their marriage weather some strain in the show’s final season. Through it all though, fans had no doubt the pair were made for each other and would be together until the end.

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Do you have any other couples that deserve to be on this Office list? Let us know in the comments!

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