This is a glorious day for Michael, a day he's been dreaming about. It is Toby's last day at Dunder Mifflin. Michael is even starting his watch to count the minutes down until Toby is officially off of work, for good.
The party planning committee meet to talk about Toby's going away party. They have already ordered a cake and are prepared to put together a Toby slideshow with two slides. Michael wants the party blown out and even throws in his own money. Angela loses her patience with Michael and all of his demands of extravagance for the party. As Angela quits the committee, Michael hires Phyllis to be the head planner of the party.
Pam gets the news she got accepted to the Pratt School of Design in New York. Jim's not phased by the idea of Pam going to New York because it is only for three months and there will be a lot of visits in between.
Toby introduces Michael to his HR replacement, Holly. Michael sets Holly straight: He's there to make the office fun and she's there to make the office lame. It isn't until she makes a crack about how boring Toby is that Michael realizes Holly is on his side.
Michael thinks he's already in love with Holly and ready to make her a mix tape. As Jim starts talking about romance to Michael, he starts thinking about his own relationship with Pam. He surprises Phyllis with cash and wants her to buy fireworks for Toby's party, but Jim's real agenda is to create a romantic setting to purpose to Pam.
Dwight decides to haze Holly to welcome her to Dunder Mifflin. He tells her that Kevin is "slow" and part of a work program. After noticing Kevin's mannerisms, Holly believes Dwight's lie. She pays extra attention to Kevin, who in turn, takes Holly's sweet gestures to mean she really wants to "bang" him.
Toby can't officially leave without his exit interview with Michael. Michael's been waiting forever to give this interview. Holly observes and Pam arrives to take notes. Michael is now forced to keep it professional, but that is thrown at the window when Toby opens his present from Michael, a rock which a note attached saying, "Suck on this".
Thanks to a video of his arrest on YouTube, the office finds out that Ryan is arrested for fraud. Jim is happy to see it happen because of the way Ryan has been treating Jim, lately. Meanwhile, Michael is crying because he's scared for his friend. Holly consoles Michael in his time of grief.
Toby's going away party begins. The office is completely surprised by Phyllis' party planning skills. The parking lot has been converted to a giant fairground, complete with a bouncy room and a ferris wheel, with the warehouse band putting on a concert. Pam also suspects Jim is planning to purpose at the party.
Michael makes a toast at Toby's going away party. He first gives props to Phyllis for putting on the best party, ever as Angela just rolls her eyes. Michael has written a song for Toby titled "Goodbye Toby" set to "Goodbye Stranger" by Supertramp.
Kevin runs into Jan at the grocery store and calls Michael up. Michael arrives to find Jan there and pregnant. Michael gets excited, until Jan breaks the news that Michael is not the father of the baby. She tells Michael that the baby is from a sperm bank and invites Michael to be her partner in her Lamaze class and Michael says he'll think about it.
Pam and Jim enjoy the fireworks show along with everybody else at the office. Jim nervously fumbles for the ring out of his pocket but before he can say anything, Andy gets up on stage with the microphone. With everybody watching (including his parents) Andy purposes to Angela and she says "okay". A hurt Dwight looks on and a shocked Jim puts the ring back in his pocket before Pam can notice.
Toby realizes he doesn't have a picture of him with Pam and Meredith offers to take one. Pam puts on a fake smile to hide the disappointment of Jim for not purposing at the party.
A distant Michael returns to the party and Holly fills him in on the Andy proposal and then asks Michael if he wants to grab dessert somewhere. Michael gently turns her down, but Kevin offers to grab a slice of pie. Holly accepts Kevin's invitation.
After sending Toby away, Michael takes some private time to call Jan. He tells her he would love to accompany her to her Lamaze class and maybe she can even teach him what a Lamaze class is. Michael admits to himself he's going to be "kind of a daddy".
Phyllis is on a high after her party was noted as such as success. She hears strange panting come from behind the Dunder Mifflin doors. She walks in to find Angela and a shirtless Dwight getting it on. They notice Phyllis and are in complete shock for being caught.