Over the years, the writers of The Office have proven themselves adept at romance. It's not something most comedy writers ever get much practice at, but thanks to the Jim and Pam of it all, The Office has had many opportunities to figure out how to make love's big milestones feel big, and funny and sweet. They brought all this experience to bear on Michael and Holly's engagement, a pretty aww-inspiring to-do that also moved us right along the Steve Carell exit trail.
Non-essential matters out of the way first: Dunder Mifflin is having their first-ever garage sale, with each employee getting a table. This sets up a couple of fun, disposable B-stories. Andy, Darryl, and Kevin play the board game Dallas, an excuse to make up the rules, put on Southern accents, and for a crafty Kevin to steal the other guys' money. Dwight sets out to prove he can barter up from a thumbtack to something actually valuable. Using head games (i.e., convincing Kelly that a half-used candle will subliminally tell Ryan she's got another man) he gets all the way to a telescope, but is ultimately foiled by Jim's ongoing insistence that a package of seeds are really magical. When Dwight falls for obvious pranks like these, we think of it as a sign of affection: subconsciously he enjoys occasionally losing to Jim.
But that's all background to the big event. At Holly and Michael's booth, Michael is refusing to part with his neon-lit, St. Pauli Girl beer sign. Holly suggests he might put it in storage, just "in case." Michael counters that he has no in case. Does she? Nope. Michael then calls Holly's father and pulls out the trademark horrible Michael Scott joke — I'm calling to fire your daughter — before getting down to his real purpose: He wants to marry her. "This is not a joke." Thanks to Holly, Michael is suffused with such a sense of calm and happiness, he basically isn't Michael anymore. Bad firing jokes aside, it's a totally appropriate, nice message. Now that Steve Carell is leaving, Michael can really grow up. At her desk, Holly calls her parents and finds out that Michael left a message. She thinks she knows what it's about, but unfortunately, her parents are so addled — this whole phone call was well done, but not funny at all — they're unable to tell her what he said.
Michael, energized by this proposal idea, has decided to write "Will you marry me?" out in kerosene in the parking lot. Thankfully, Pam is on hand. She's very happy about the proposal, but scurries off with the gasoline and matches: "You've had two ideas today, and one of them was great, and one of them was terrible." Cue an intervention. Pam brings Michael into the meeting room, where she, Jim, Oscar, and Ryan attempt to help him figure out how to propose. This whole premise here is so kindhearted. When Michael walks in, Pam says, "We are a family, and I've always believed we should all be very involved in one another's personal lives in a very major way." This is totally the opposite of what Pam generally believes, but she cares so much about Michael, she can't leave him alone to mess this up. The group wants to help make the proposal "safe and responsible and realistic and doable."
Meanwhile, Holly talks to Phyllis about her parents: When did she know they needed help? Phyllis basically says they never get better. Holly tells Michael that she thinks she needs to go home to Colorado to take care of her dad, while he's still her dad. Mensch Michael is very supportive. Holly asks him to come with her, and starts to propose. Michael shushes her and walks out: "No, i am not going to be proposed to in the break room."
And thus we come to the big sapfest. Michael takes Holly on a walk around the office, pointing out key places: "This is where we first kissed," "Through these blinds is where I first saw you," "I was sitting at this desk and I called to tell you I had herpes and I still loved you," Holly does an amazing Michael Klump impersonation, and then Michael opens the door to the break room. The entire office is lining the walls, holding candles. Each asks Holly to marry them as Michael ferries her past. She says no to each and every one. While this part of the proposal is strangely communal, it's a hat tip to the fact that long before Holly, it was the office that was civilizing Michael. They've put in years of explaining right from wrong, of trying to get him to behave, of being stuck with him in the way you're only stuck with your family. And those are the years that have made him into the kind of man who can make this step, this right step, this grown-up step, with the right person. They're sending him down the aisle.
Holly and Michael walk into a room covered in candles. He says, "This is where i fell in love with you, and this is where I asked you to marry me." Cue tears, and the Dundler Mifflin sprinkler system! Covered in water, Michael asks Holly to marry him in Yoda voice. She accepts in Yoda voice because she really is perfect for him. They kiss, everyone cheers, and Michael tells them all that he's moving to Colorado: "I'm leaving." It's a testament to the new Michael that everyone looks really upset.