Though The Office provided lots of laughs, it also served up many romantic moments.
The popular mockumentary sitcom, which aired on NBC for nine seasons from 2005 to 2013, had viewers consistently wondering who would end up together next. With many relationships forming throughout the series, there were naturally a lot of proposals that played out.
While some couple’s engagements happened on-screen in big, dramatic ways, others happened away from the camera and were later revealed to the audience. We’re here to look at both kinds of proposals and stack them up from worst to best. With that being said, it’s time to head over to Scranton and get ready for some romance.
8 Ryan And Kelly
Though we never see Ryan get down on one knee, the couple claims to have gotten married soon after getting wasted together. They later get divorced after spending a weekend together in the Poconos, during which they watched the sunrise a lot. Apparently, Ryan also shed a tear or two.
Being that the couple got together on a whim, we doubt the “proposal” (if you could even call it that) was very romantic. Nope.
7 Michael And Carol
Though Michael barely knows his relator Carol Stills, he decides it’s a good idea to get engaged to her during Kelly’s Diwali celebration in season 3.
Carol showed up to the event in a cheerleading outfit after Michael mistakenly told her that it is a costume party. After Michael learns of Hindu marriage customs from Kelly’s parents, he feels the need to propose to his girlfriend right then and there.
Carol refuses his marriage offer and drives home alone. Though the pair doesn’t break up right away, they do later after Carol cites how uncomfortable Michael made her feel by photoshopping his head onto that of her ex-husband’s in an old family photo.
6 Pam And Roy
When The Office begins, Pam and Roy are already engaged. Pam doesn’t seem very happy, being that she’s had a ring on her finger for 3 years and the wedding still hasn’t happened.
That being said, in the season 2 episode “Booze Cruise,” Roy performs what you could call a second proposal as he finally sets a date for the wedding.
This occurrence happens while the office is partying it up on a boat in Lake Wallenpaupack. Inspired by a tale told by the ship’s Captain Jack, a wasted Roy decides to ask Pam to marry him for real this time. Though Pam was excited in the moment, the circumstances surrounding this proposal weren’t so gleeful. Jim is heartbroken to know the love of his life is about to tie the knot with another man.
5 Andy And Angela
Though Andy and Angela’s romance is doomed from the start, with the majority of their relationship coming off as one-sided, Andy’s proposal to Angela isn’t so bad.
During the Season 4 episode “Goodbye, Toby,” Jim plans to finally pop the question to Pam. The office is throwing Toby a farewell party as he is about to head off to Costa Rica, and Jim decides that this is the perfect time to propose. He even contributes extra money to the event so that fireworks can go off at the right moment.
Unfortunately, Jim’s plan backfires when Andy, enchanted by the perfect conditions, takes the opportunity to propose to Angela right before Jim can ask Pam. Though Andy’s question is sweet, Angela acts annoyed by the proposal. She accepts bitterly.
4 Phyllis And Bob
While we don’t know much about Phyllis’ engagement to Bob Vance, we find out that it has occurred in the season 3 opener “Gay Witch Hunt” after Michael questions Phyllis’ sexual orientation. She holds up a ring and tells the group that she is engaged.
Being that this the extent of the information revealed to us, we have to assume that their actual engagement was better than the ones earlier on the list since none of those lasted. That being said, there’s no way Phyllis’ engagement could have topped the ones to come.
3 Pam And Jim
Not many moments on The Office can beat the scene in which Jim proposes to Pam.
In the season 5 episode “Weight Loss,” Jim pops the question outside of an interstate gas station in the rain. He tells her he couldn’t wait any longer.
Though the moment is simple, her reaction is everything. With Pam about to start a three-month graphic design program in New York City, the timing could not be more opportune.
2 Angela And Dwight
Though Angela and Dwight aren’t The Office’s “power couple,” they are the pair everyone was waiting to get together for a long time. This finally happens in the season 9 episode “A.A.R.M.”
Dwight tries to get Angela’s attention by putting a flashing light on his car and pulling her over. Though she’s angry when he veers her off the road, she calms down after he tells her he’s in love with her through a megaphone. He also promises to raise Philip as his own, even if they’re not blood-related.
Dwight pulls out a ring taken from his grandmother’s butt and Angela accepts his proposal. She then reveals that Dwight is actually Philip’s father after all. The moment is insane and sweet.
1 Michael And Holly
Topping off the list as the best proposal of The Office (and perhaps one of the best TV proposals of all time) is that between Michael Scott and Holly Flax. Though viewers waited a long time to watch Pam and Jim get engaged, they waited even longer to see Michael end up in a good relationship. He finally gets his happy ending in the season 7 episode “Garage Sale.”
Holly gets the hint that Michael is about to propose, learning that he called her father to ask permission. Concerned that her parents aren’t doing well, however, she considered moving back to Colorado.
Nevertheless, Michaels later walks Holly through the Scranton branch as he tells her of important moments in their relationship. When he gets to the kitchen, he opens the door to reveal everyone waiting around with candles. Holly says “no” to each employee who asks her to marry them, and finally, Michael gets down on a knee to pops the question himself (after getting drenched by the fire sprinkles, of course). She says yes.
Michael then reveals to the gang that he’s moving to Colorado with Holly. This bittersweet moment is unmatched.
