John walks into the diner, but there's a young guy with blue hair sitting in his chair, so he lies about the guy's bike being peed on by bums so he'll get out of his seat. After John sits down, he complains about the guy's hair to Reggie, but she says he was just expressing himself. Jake comes out of the bathroom, and John tells him his fly is down, but Jake thinks he's lying, but Reggie says he looks fine. Jake ends up leaving with his fly down to see his girlfriend. Why did Reggie do that? She says Jake has been bothering her all morning.
At the office, John asks Margaret why she didn't remind him about the children's fundraiser, but she did. She pulls out a voice recorder to prove it. John doesn't want to go to it because it's a black tie affair and doesn't have a date. Margaret suggests taking Reggie, but John doesn't like that idea.
At the diner, John walks in to see Jake tending the counter, since Reggie is out shopping. Jake tells John his date didn't go so well. John then tells him about the dinner on Sunday. Reggie comes in complaining about the price of the clothing she bought. When she goes to the back of the diner, Jake suggests he take Reggie, but John still isn't into the idea.
John walks into the office to see a patient of his who has a broken collar bone. He asks him to explain how it happened, but he's reluctant to to say because he thinks John will laugh, but John says he won't laugh, so he starts explaining what happened. He was at a construction site when he needed to use the bathroom, but when he gets in the porta-potty, when a crane picks it up and puts it on a truck. As the truck is going down the road, it fell off the truck, and right in front of a school, embarrassing the heck out of him. John is containing his laughter through the whole story, but when he leaves the room, he can't help but burst out laughing. John walks into his personal office, laughing, when Margaret comes in to tell him she has his suit for the benefit, but he still refuses to take Reggie, and goes off on a rant with reasons. Margaret recorded the entire conversation, surprising John.
John walks into his apartment when he notices his super in his apartment. He finally fixed his shower. The super sits down and tries to come up with someone for John to take the benefit. He oddly suggests Reggie, but John tells him they're not for one another. There's then a flashback of John as a kid, where he asks a girl to the dance, but it didn't go so well back then either.
Reggie walks in to the diner, as Jake is tending to the counter again. John comes in and thinks about asking Reggie out, but doesn't.
John goes back to the office to see a patient who seems to be really tired all the time. She seems to be busy all the time with her four kids. John walks out of the room when Margaret says there's a problem with a patient of his. He asks her to tell him to drop his medication to 5 mg and come in to get his blood pressure checked. Margaret then tells him that Pam called and left a message. She won't go with him because of the way their last date went. John goes back in to see the woman who is tired all the time, but when he goes in, she's asleep. John covers her up with her jacket, turns off the light, and closes the door. John then walks into his personal office, when Linda and her friend come in. Linda suggests he take her friend to the benefit, but John isn't the least bit interested.
At the office, Margaret is laughing when she reads the profile of the man who fell with the porta-potty, off the truck. The woman who was asleep in the other room, wakes up and comes out, yelling at John for letting her sleep so long, but John says not to worry about it. He's taken care of things, and suggests that he can call a few of his retired patients who may be able to take care of the kids for her on occasion. As she's going out the door, she brings up the children's benefit and suggests taking Reggie, so he closes the door in her face.
John drops by the diner to ask her out, but she says no because it sounds boring.
There was a flashback scene of John when he was 10 years old that was absolutely hilarious. I was shocked at how accurate the young child was at portraying John.