John comes into the office complaining about everything, and notices no one else is there. Margaret comes in and and tells John about them having a staff meeting. Linda comes in with a big box of donuts for the meeting. They're from Krispy Kreme, and John doesn't think they're as good as they claim, but when he tries one, he falls in love with it. Since John doesn't really want to be at the staff meeting, he decides to take a very unimportant phone call in his personal office.
At the diner, Reggie and Jake are listening to Bob, who is reading things from the advice column. John comes in and a woman from Harvard calls the diner, and gets in contact with John. It turns out the woman was actually in the diner's pay phone. Megan works for the alumni and is trying to get donations, but John doesn't want to give her his money obviously. They leave when she offers to buy him dinner.
At work, John's about to leave to meet Megan, but Margaret insists that they have a staff meeting. When Margaret can't find a red folder, John and Linda leave. Linda hid it in the microwave.
At dinner, John and Megan talk about old times, and how things are going now. They end up kissing as they evening ends.
John walks into the diner to talk to Jake, but he asks Reggie to leave, so they can talk in private. John tells Jake about what happened last night and John wants to sleep with Megan, as they used to go out together, but she's married now.
Back at the office, Margaret finds her red folder and has another staff meeting. It turns out they're being double-billed for medical supplies by someone, cheating John out of money. John seems to draw parallels between that and his thing with Megan, making for an awkward moment at the meeting.
After another night out, John and Megan wind up at her place. As they're making out, John begins to imagine all of his friends being in the room, criticizing him for what he's doing. John eventually leaves after he had enough of the criticizing.
This was a very funny episode, well acted and written. The final scene was hilarious, as John continued to run into his friends.