Jim and Pam are Dunder Mifflin's resident favorite couple. They were best friends who pined for each other for a long time before putting their fears aside and giving their relationship a chance to blossom. But before Jim and Pam were Jim and Pam, she was with warehouse worker, Roy Anderson.
It was hard for Pam to move on from Roy because she had been with him for so long. In fact, their relationship has so much history that it often gets brushed under the rug because Office fans were so focused on the potential she had with Jim. However, her relationship with Roy should still be respected for what it was because without it, she'd never be with Jim.
How Long Were Pam & Roy Together, Again?
In the pilot episode, fans assumed Jim and Pam were single and crushing on each other until they found out Pam was not just dating Roy but engaged to him. At this point, they were together for eight years and engaged for three. By the time she finally called off their relationship, Pam and Roy were together for a decade. That's a long time to be with someone, but it's obvious they were both unhappy. It wasn't until Jim confessed his feelings that Pam realized she wasn't happy with Roy.
Their Song
Although it was Phyllis' wedding, it was a big episode for Pam and Roy because Phyllis stole all of Pam's ideas from her wedding. Pam and Roy were essentially walking into their wedding but it wasn't them getting married. All of this, plus seeing Jim be so happy with Karen, was a lot for Pam to take. It was an emotional day. Things got weirder when Roy noticed that the flowers Phyllis picked out were the same flowers he gave Pam at prom.
By the end of the night, Roy told Pam he gave Kevin $20 to play "You Were Meant For Me" by Jewel because it was their song. The two slipped away to dance in private as Pam slowly went back to him.
The Forgotten Date
While the employees of Dunder Mifflin were in the kitchen, a group of them went around telling the worst dates they've been on. Pam tells everyone that one time she went on a date to a hockey game with her boyfriend and her boyfriend's brother. At the end of the game, she went to the bathroom but when she came out, her date was nowhere to be found. They forgot about her and left the complex. When Jim asked Pam how long ago this happened, the look on her face explained it all — it was Roy.
How They Met
Diehard fans know that Pam and Roy met when they were teenagers and were high school sweethearts. However, the details of that young relationship were not given.
In an episode of the Office Ladies podcast, Jenna Fischer said she created a backstory for Pam and Roy to make their relationship more convincing. She thought Pam and Roy met through Pam's family business. Roy got a job there while the two of them were in high school and started dating shortly after. Because of the close bond they had with each other's families, it made it harder to end that relationship.
Not Enough Money For The Wedding
Being engaged for three years meant that Roy and Pam had plenty of time to plan and save for a wedding. However, while they were saving money, Roy decided to blow it all on a pair of jet skis for him and his brother. Pam doesn't seem like a jet skiing kind of gal. She would have preferred to get married than do watersports any day. After Roy did this, it was clear to Pam that he wasn't serious about their relationship.
Roy Sensed Something Between Jim And Pam
Even though Roy was shocked to the core that Pam and Jim kissed, he always sensed something was going on between the two of them. Even if he didn't outright say it, his actions spoke louder than words.
In a scene in the first season, Jim and Pam are chatting at reception when Roy came in. Though he said nothing, the look on his face was clearly one of discomfort. Later in the episode "Basketball," Roy elbowed Jim when Jim played better than him. Roy obviously didn't want Pam seeing him lose to another guy in the office. Roy tried to push Jim away yet again when Jim started talking to Katy the purse girl. Even though he didn't say it, Roy always felt threatened.
Roy Chose Angela Over Pam
In "The Fire," there was a fire in the office and Dunder Mifflin employees were forced to wait outside while the firefighters put it out. To pass the time, the gang started playing games and asking questions. In one game, Roy said he would sleep with "the Christian girl," Angela. Meanwhile, his fiancée Pam was standing right next to him.
He Never Did Get Pam An iPod
In the episode "Christmas Party," Jim gave Pam the iconic teapot filled with fun memories they had together. Jim's plan went awry when Michael bought an iPod and entered it into the White Elephant Christmas game, and Pam gave up the teapot and took the iPod.
By the end of the episode, Pam revealed that she got rid of the iPod so she could keep the gift from Jim. Roy was supposed to get Pam an iPod for Christmas anyway. A couple of episodes later, however, Pam was using an MP3 player. She told Dwight it was a gift from Roy, which only proved that Roy cheaped out and bought her something less expensive instead of getting her exactly what she wanted.
Even Their Save-The-Date Was Open-Ended
After Roy had an epiphany in "Booze Cruise" and re-proposed to Pam on the boat, they decided to have a summer wedding on June 10th. Angela showed the save-the-date to the camera and its lackluster design is shocking considering it's coming from someone with a love of art.
Angela mocked the save-the-date and said it wasn't her taste. And to be frank, it doesn't look like Pam's taste either.
Dressed To Impress
When Pam's mom first came to visit, Pam was very eager to show her her workspace and introduce her to Jim. But suddenly, Roy appeared from the warehouse but not in his traditional outfit... This time, he wore a nice dress-sweater and his hair was combed.
Roy was clearly trying to suck up to Pam's mom and make it seem like he's always this put-together but that couldn't be farther from the truth. Roy only visited Pam when he was ready to go home for the day and he was always in his work clothes.