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 every The Office Couple, Ranked From Worst To Best.
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.
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.
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.
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.
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.
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 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.
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 unive 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 its she kissed Jim, she promptly breaks up with him for the second time. Thankfully this time it was for good.
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.
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.