‘The Office’: How Long Were Pam and Roy Engaged?

Before there was Jim and Pam, there was Roy and Pam. The not nearly as cute, unsupportive, almost-made-a-huge-mistake-by-getting-married couple from the beginning of The Office.

We’ve all become so enthralled with Jim and Pam that it’s hard to remember the details about Roy and Pam’s relationship. Well, don’t worry. The Cheat Sheet is here to help fill in all your Roy and Pam memory gaps.

How Did Roy and Pam meet?

Roy and Pam The Office
David Denman as Roy Anderson and Jenna Fischer as Pam Beesly in The Office | Chris Haston/NBCU Photo Bank

Roy (played by David Denman) and Pam (played by Jenna Fischer) met in high school. Roy was a jock and Pam was, as Roy described her, “Miss Artsy-Fartsy.” Since the show begins long after high school, we don’t have a lot of knowledge about this time period. However, we do know about their first date because it’s described in Season 1. Roy brought Pam to a minor league hockey game, along with his brother.

Then, while Pam was in the bathroom, he forgot she was there, and he left without her. It isn’t explained why Pam didn’t dump him right then and there like any normal woman would. But, maybe it’s because he was handsome and popular. After high school, the couple ended up working together at Dunder Mifflin, Pam as a receptionist and Roy in the warehouse.

How long were Roy and Pam engaged?

Roy and Pam were engaged for three years before the show starts. During the first and second seasons, we see them planning their wedding, but many fans were left confused, unsure why Pam wanted to marry him in the first place.

He wasn’t supportive of her art career ambitions, and he seemed to take her for granted. For example, on Valentine’s Day, Roy doesn’t get her anything, but instead tells Pam that when they get home, she’s going to get “the best sex of her life.” Pam responds with a deadpan look.

How did Roy and Pam’s relationship end?

Things start to go downhill for Roy and Pam when Jim confesses his feelings for Pam at the end of Season 2.

Pam starts to really think about what she wants out of a relationship. Even though things don’t work out with Jim right away, Pam decides that Roy isn’t right for her, and she breaks off the engagement. This leads to some awkward encounters since they still work together at Dunder Mifflin. Including the pair being stuck eating all the meals from the caterer for their lunches, that were already paid for, intended for the wedding.

Roy and Pam briefly get back together at Phyllis’s wedding. The event holds a lot of memories for the couple because Phyllis stole many of the ideas Pam was going to use for their wedding.

Roy gives Pam a heartfelt talk about their history and then pays the wedding band (Kevin’s band, Scrantonicity) $20 to play their song (“You Were Meant for Me” by Jewel). Roy and Pam end up leaving the wedding together.

It’s not long until the couple breaks up a final time. Pam confesses to Roy that she kissed Jim during Casino Night, and Roy goes berserk. He trashes the bar they’re at, and Pam ends the relationship right there.

The next day at Dunder Mifflin, Roy tries to punch Jim, stopped only by Dwight with pepper spray. Roy gets fired, and this, coupled with losing Pam, sends him into a depression tailspin.

Did Roy get a happy ending?

Most of us know that Pam ends up with Jim. Shortly after calling things off with Roy, she starts dating Jim, and soon the pair are engaged. Jim and Pam get married and have two children. They go through some rough patches, but when the show ends, they seem happy together.

What about Roy? In Season 9, Pam and Jim are invited to Roy’s wedding. Roy pulls Jim aside and actually thanks him for stealing Pam away. Losing Pam gave Roy the motivation he needed to get his life together. He started a gravel business and made a ton of money, as evidenced by the sports car he’s now driving.

Roy is head over heels for the woman he eventually marries. He turns into a sweet, loving man that actually learned the piano to sing his new wife a song on their wedding day.

One of the things that’s so great about The Office is that everyone ends up with a happy ending, and it doesn’t feel cliche. It actually feels just right.