Hector walks in to the diner, and Jake is excited to see him. Jake asks him if he would go and pick up some tickets for him, but he refuses to since Jake wouldn't take Hector to the concert. As Hector leaves, John walks in and gets news about an old friend in town. Jake asks John if he would go and pick up the tickets for him, and he agrees to, and then John suggests to Chris that she make arrangements for the dinner with his friend, and she would come with. She's a little surprised by the request, since she's never met any of John's friends, and is a little concerned about how she'll be introduced to his friend.
At the office, John tells his patient that he doesn't have any disease, he's just a lazy bastard. Linda was working on the computer, when all of a sudden there is a "fatal error" message on the computer. There's a file containing medical insurance information that's missing.
On the subway, John helps a woman get directions after she's lost. She took the wrong train and is on the wrong side of town. He ends up losing his seat in the process.
At the diner, John's friend and his wife enter, and Chris introduces herself to them, but the wife seems rather rude.
Back at the office, Margaret and Linda are tying to think of ways to get the computer file back. Linda suggests that they start a fire and burn down the office; the insurance will cover it. Margaret decides to call the computer guy and take the money it costs to fix the problem, out of Linda's paycheck.
Back on the subway, John's still trying to explain things to her, but she's terrible with directions, and they try to find a pen and paper to write the directions on. John's pen ends up getting broke in half, and they never found a piece of paper.
Off of the subway car, John's late for dinner, and is stuck with the woman who is lost, and she still doesn't understand the directions. John decides to take the woman to wherever it is she was going to go.
Back at the diner, Dickey's wife is still acting rude.
Back at the office, Margaret was able to find the file after contacting the computer guy. Margaret accidentally reveals she was the reason the file got lost, not Linda. Margaret has to apologize after Linda yells at her and says she does a lot more around the office that she doesn't get credit for.
At the diner, Jake is on the phone with John's answering machine, asking where his tickets are. Dickey tries to tell Chris a story, and ends up insulting his wife on purpose. Chris is angry about the way the evening has gone, saying John only cares about himself.
John helps the woman get to the street she was wanting to go to, but she won't go any further on her own, she can't. John gets upset that she came all this way and now won't finish her trip. She tells John it would have been her son's 40th birthday that day, and she recounts that he had called her from his office to chat on a clear September morning. You can see by the change in John's face that he's already put the pieces together. She continues about how he had a meeting to go to and he said he'd call her later and hung up. She went about her chores and then happened to turn on the TV. She tears up as she tells John how she thinks of all the things she would have said if she knew it was the last time she would talk to him, and how she just can't go look at all that empty space. John takes her hand and sits there with her quietly.