John comes into the diner complaining about quitting smoking. Jake then walks in with a raspy voice, as he was up crying about Amanda leaving him. Chris gets a call and it seems her ex-husband is in town and will come by. Bob asks John if he's curious what he's like as Chris shot him down several times, and perhaps he may want to see just who made the cut. When Chris's ex comes in, John laughs because he's somewhat short for a man and looks pretty young. Bob makes a joke about him being less of an Indiana Jones and more Harry Potter. Chris and her ex leave to go around town a little.
John walks into the office, happy about there being a parking spot right out front, the first time in ten years. He also mentions how he met Chris's young ex-husband, Roger... so, it's been a pretty good day for John.
Back at the diner, Jake's depressed as heck, despite being hit on by a woman over the phone. Bob realizes the way to pick up a woman is to act depressed, just like Jake was, so he walks out. John comes in and asks about Chris and Roger. Jake mentions they haven't been back yet, which is surprising. A few seconds later, Roger and Chris come in. John asks Roger about his plans with his upcoming trip to Australia, and it seems Roger is quite an adventurous man, so John tries to impress him with old stories, but fails miserably. Chris hands Roger the key to her apartment, and John asks her about it. He's going to be staying with her since it's too expensive for a hotel room.
The next day, Chris brings food into the office, and she's curious about why John likes his parking spot so much. Chris, Margaret, and Linda end up getting into a big discussion about sex, and it seems Roger is great in bed. John comes in and he doesn't want to hear about any of it.
Realizing Roger and Chris could be having sex, John runs over to Chris's apartment, and brings videos and food. He sits down between them on the couch.
A bit later in the evening, Chris is almost asleep because they're watching boring war movies. Finally, Chris decides to go to bed and Roger confronts John about why he's there. John ends up leaving because of an emergency call from a patient with a bleeding ulcer.
At the diner, Bob tells Jake about how he's going to try to use the pathetic, lonely trick on a woman. When woman comes in, Bob tries it on her, and even gets her number. When he looks at the business card she gave him, he realizes she works for the Suicide Hotline. Bob walks out when John comes in for coffee and realizes Roger is asking Chris to go to Australia with him.
Back at the office, Linda gets Margaret to take the blame for not feeding the parking meter, which resulted in John's car being towed away. When John comes in, he doesn't care about the car, he's only got his mind on Chris.
At his apartment, John's confronted by Chris. They end up getting a big fight over it. When she leaves, it seems she regrets her decision about not going with Roger to Australia.
This episode added some character development, as we got to learn a little more about Chris, thanks to the appearance of her ex-husband. It's beginning to look better for John.