Office Romances

Office RomancesToby once warned everyone that office romances are never a good idea, but that certainly hasn’t stopped anyone at Dunder-Mifflin from engaging in inner-office relationships, crushes, and flings. Here’s a guide to the past and present Office Romances. (current through “Cocktails”)

Click the couple name to learn more.
Jim and Pam
Dwight and Angela
Pam and Roy
Michael and Jan
Jim and Karen
Ryan and Kelly
Toby and Pam
Andy and Pam
Angela and Roy(?)
Meredith and every male co-worker(?)
Jim and Brenda Something(?)
Karen and Drake/Married Guy/CFO(?)
More relationships to come

Jim and PamJim and Pam (JAM)
unrequited love
when: 2002 – present
It was apparent from the beginning that salesman Jim Halpert had a very deep crush on the engaged receptionist Pam Beesly. Pam considers Jim to be her best friend, but as time goes on Jim’s feelings only deepen. At the beginning of 2006, Jim nearly tells Pam his feelings for her but minutes later Pam and Roy set a wedding date. As Pam becomes more engrossed in planning her wedding, Jim plans a transfer. A month before her wedding, Jim confesses to Pam that he’s in love with her. Pam replies that she “can’t” and Jim walks away with his head hanging. A few minutes later, Pam is talking to her mom on the phone up in the office, when Jim walks in and without a word walks up and kisses Pam. Pam admits she’s wanted to kiss him for a long time, but as he goes for a second kiss, she tells Jim she’s still going to marry Roy, and Jim transfers to Stamford. However, Pam cancels the wedding a few days before the date. Jim and Pam have little contact before the Stamford and Scranton branches are merged. Pam is excited to have somewhat of a “second chance,” but Jim starts dating Karen and keeps his distance from Pam. They slowly reconnect, but hit another snag when Karen confront Jim about having feelings for Pam. With Jim more committed to Karen than ever, a very lonely Pam decides to rekindled her relationship with Roy. She and Jim have had minimal interaction since, though she confessed to Roy she had had feelings for Jim when she was engaged to Roy. top

Dwight and AngelaDwight and Angela (DWANGELA)
when: Nov 2005 – present
At first, religious control freak Angela was at odds with Dwight, the fiercely loyal Assistant (to the) Regional Manager that somehow still suffers from delusions of grandeur. However, one day Pam notices Angela buying two candy bars, and later that day the cameras catch the Birkenstock-wearing couple cuddling at Jim’s barbecue. They’ve tried to keep their relationship a secret from their coworkers and the cameras, but their “inconspicuous” behavior only makes it more obvious they’re together. In late 2006, Angela encourages Dwight to make a run for Michael’s job, but it only ends in humiliation. In early 2007, Dwight secretly delivers some tax files Angela forgot to send to the corporate office in New York. Andy alerts Michael that Dwight went to New York and convinces him Dwight is making another run for his job. Michael confronts Dwight, and Dwight, unwilling to reveal his secret relationship to Angela, decides to quit. However, not long afterwards, Angela tells Michael Dwight went to New York for her, and Michael rehires Dwight. So far Pam is the only one that knows about Dwight and Angela (though several other employees probably suspect). top

Pam and RoyPam and Roy (RAM)
when: 1997ish – June 2006, Feb 2007
Pam and Roy were high school sweethearts and had been engaged for a few years when we first met them (hence Pam’s multiple “World’s Longest Engagement” Dundies). It was clear Roy was a bit controlling in the relationship, and rarely encouraged Pam. They were set to be married on June 10, 2006, but without warning Pam called off the wedding a few days before. Pam didn’t seem incredibly regretful about their broken engagement, but Roy was and resolved to win her back. In February 2007, at Phyllis’ Wedding, Roy reached out to the lonely and dejected Pam and they decided to rekindle their relationship. However only a couple weeks later, Pam confessed to kissing and having feelings for Jim, and Roy lost it and threw some beer bottle. Pam walked away uttering, “This is Over.” top

Michael and JanMichael and Jan (JACHAEL, MAN)
fling, eventually relationship
when: “Flings” in Nov ’05 and Feb ’06, couple from Jan ’07 – present
At first, the possibility of a Michael and Jan hook-up was just one of Michael’s unrealistic fantasies. However, in late 2005, after landing a big client and having a few margaritas, Jan and Michael kiss and end up spending the night together. Jan tries to deny it ever happened, but thanks to Michael’s big mouth, every level of the company learns about it. In May 2006, Michael ends up inviting both Jan and his real estate broker Carol to the Casino Night party at the office. Jan sees Michael is more interested in Carol, and is embarrassed for expecting something to happen. For the next few months, Jan tries to keep her relationship with Michael professional, but after Carol dumps Michael, Jan agrees to go with Michael to Jamaica. In February, 2007, Jan and Michael “make it official” and come out as a couple at a mangers party. Though Michael’s embarrassing behavior should be their main problem, it’s actually Jan’s libido that makes things between them uncomfortable. top

Jim and KarenJim and Karen (JAREN, KARIM, KIM)
When: Nov 2006 – present
At first, Stamford saleswoman Karen didn’t seem incredibly impressed with Jim, nor with the fact that he was her superior. But after a few pranks and some mild flirting, it was clear Karen had developed a crush. When it is announced the Stamford branch is closing instead of Scranton, Jim, wrestling with the idea of moving back to Scranton and seeing Pam again, encourages Karen to come to Scranton. Jim starts seeing Karen soon after moving back to Scranton, but he takes things fairly slow. A month into their relationship, Karen, still living in a hotel, finds a place near Jim. Jim is uncomfortable with Karen living down the street, but get some unexpected advice from Pam. A couple weeks later, Karen learns about Jim’s crush on Pam. Soon afterwards she asks if he still had feelings for Pam, and Jim answers that he does. It seemed like the end of Jim and Karen, but they spend 5 long nights talking, and decide to stay together. Their relationship sees another boost when Pam gets back with Roy, and Jim starts devoting himself more fully to Karen. He turns to Karen when he wants to pull a prank, and Karen even pulled a prank of her own on Jim when she convinced him she had dated several men in the company. top

Kelly and RyanRyan and Kelly (KRYAN)
when: Feb 13, 2006 – present
When Kelly made Jim play matchmaker for her and Ryan, Ryan just wanted a hook-up, but then stupidly got together with Kelly the day before Valentine’s Day, making the obsessive Kelly more than ecstatic. Ryan hoped Kelly would eventually lose interest by acting indifferent on dates and while meeting her parents, but Kelly has only latched on to Ryan tighter. Ryan tried to take advantage of the news that the Scranton Branch was closing and suggests to Kelly it was best to break up. However, when it’s revealed the Scranton Branch was to remain open, Kelly attacks hugs Ryan, and an oddly affectionate smile crosses his face. In the deleted scenes of “A Benihana Christmas,” Kelly tells Ryan she’s had enough of his inconsiderate behavior, and once again Ryan tries take advantage of the opportunity to break up, but Kelly then forgives him. After Ryan humiliated Michael at his business school, Michael punishes him by moving him to the back room next to Kelly. top

Toby and PamToby and Pam (POBY)
when: Late Sept 2006 – present
When Kevin tells Toby that Pam is starting to date again, Toby’s interest is piqued. He spends the day trying to get Pam’s attention, and nearly asks her out before losing his nerve. At Christmas, Toby is touched when Pam give him a Dunder-Mifflin robe after Michael took his away for some unknown reason. Later, in “Traveling Salesmen” (deleted scene) Toby asks Pam to give him a coffee, but when it doesn’t lead to any conversation with her, he tosses it out. In February, Toby nearly bails on his daughter’s play to go to Pam’s first art show, then a week later when Pam comments how cute a stuff animal is in a vending machine at Poor Richard’s, Toby spends half the night trying to win it for her. He presents the stuffed duck to her, but then Pam graciously rejects it, telling him he should give it to his daughter. top

Andy and PamAndy and Pam (PANDY?)
when: Nov 2006
Soon after the Stamford branch merged with Scranton, Andy calls Jim, hoping Jim can help him hook up with one of the office ladies. Andy mentions Pam, and Jim can’t pass up the opportunity to prank Andy and Pam at once. Jim “coaches” Andy by giving him a list of things for Andy to talk about/do (which is really as list of the things Pam hates). Andy makes a move on Pam by suggesting they throw a Frisbee around, listen to country music, and asks (in Pig Latin) what Pam thinks. Pam is stunned and unable to respond, then sees Jim was the one that unleashed Andy on her. At the end of the episode, Andy serenades Pam with his banjo, singing in a “sexy falsetto voice,” but it’s assumed Pam eventually turned Andy down and he hasn’t hit on her since. top

Angela and RoyAngela and Roy
crush (unconfirmed)
when: unknown
It’s nothing obvious, but Angela and Roy seem to have this odd little attraction to one another. In “The Fire,” during the “Who would you do?” game, Roy mentions Angela. In “The Secret”, Phyllis asks Angela who she would chose between Roy and Jim, and after lecturing Phyllis about gossiping, Angela chooses Roy. Finally, in “Branch Closing,” (the Producers cut, I believe?) when Roy worries about his job (and Pam’s job), Angela seems mildly flirtatious as she told him he was “strong and capable” (and Kevin seems to notice it too). top

MeredithMeredith and every guy in the office?
fling (unconfirmed)
when: many occasions over the past several years
Meredith’s #1 relationship seems to be with vodka, but she has also allegedly hooked up with many office men. Dwight first tips us off to Meredith’s promiscuity in “Sexual Harassment,” and a few months later Meredith gets cozy with Todd Packer and takes off her top in front of Michael. When Jan informs everyone the Scranton branch was closing, Meredith tries to find the male co-worker she made a pact to sleep with on their last day, learning it was an old warehouse worker (Branch Closing, producers cut). top

Jim and Brenda?Jim and Brenda Something from corporate
(brief) relationship/dating (unconfirmed)
when: Late Jan -Late March 2006?
Stuck in the back room next to Kelly for the day and faced with the reality of Pam’s wedding, Jim decides to call Brenda from corporate who he met on “Booze Cruise.” He leaves a message asking her out, making Kelly proclaim “you just asked a girl out on the phone!” A few weeks later, in “Take your Daughter to Work Day,” Jim leaves early to go on a date (possibly with Brenda). Then, in “Drug Testing” deleted scenes, Pam tells Jim (who is not allowed to talk under “jinx”) Brenda is on the phone, but Jim cannot answer, and apparently Brenda didn’t leave a message. top

Karen and Who?Karen and Drake/Married Guy/CFO?
relationship/dating (unconfirmed)
when: unknown (before Nov 2006)
Next to nothing is know about Karen’s relationship past (Andy once mentioned he and Karen kind of had something, but this seems to be mostly in Andy’s head). But at the managers’ party in “Cocktails,” Karen points a man named Drake and tells Jim she use to date him, and “it didn’t end well.” Later, Karen and Jim are talking to a married couple, and Karen tells Jim she saw the husband for a little while when he was separated from his wife. Towards the end of the night, Karen tells Jim to be cautious around the CFO because he may still have feelings for her. Jim snaps at Karen, and Karen reveals it was all a joke. But then she jokes that Jim is her “first” so whether she went out with any of the men or not is still a bit of a mystery. top


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