The episode opens with Tucker saying goodbye to Libby as she heads off to work as a camp counselor. Tucker tells her not to worry about him since his friend Oliver will be around to keep him company. When Tucker arrives at Oliver's family winery, Oliver is driving a forklift and challenges Tucker to a race with his Ferrari. While driving, Oliver has trouble keeping his eyes open and crashes the forklift.
In town, Eddie arrives late for lunch with Evan. Eddie proposes having a barbecue at Ms. Newberg's home when she comes back, but Evan says Hank will never come. He tells Eddie he doesn't want to be the middleman between his father and brother anymore.
Tucker calls for HankMed and they meet Kim, who is in charge of the wine making. Divya notices her taking pills and finds out she is having headaches which she claims is due to the pressures of upcoming event. Divya gives her a business card and recommends she see Hank. Hank examines Oliver and finds nothing wrong except for blood under his toenail. While Hank treats the toe, Oliver falls asleep indicating something else might be wrong. Divya takes some blood samples to check for mononucleosis.
At the hospital to drop off the blood samples, Divya runs into Jill who is having nausea and cravings for strange foods. Divya asks how long it has been since Jill and Hank broke up, implying a possible pregnancy. Later at the pharmacy, Divya buys a pregnancy test for Jill so Jill can avoid gossip. Evan sees Divya browsing the pregnancy tests and thinks she is buying one for herself. He leaves without her seeing him. Jill uses the test kit and verifies that she is not pregnant.
At the winery event, Hank tells Oliver that the tests ruled out mononucleosis, but he is still waiting the rest of the results. He recommends an MRI, but Oliver thinks he is going overboard. Divya notices Kim taking more pills and asks her if she has seen her doctor. She reveals she has only been there a few weeks and her insurance doesn't cover her yet. Evan sees Divya standing at the bar with a glass of wine and thinks he might know something when she decides not to drink. Kim tests Evan's response to several wines and when he correctly names the flavors, Kim says he might be a super-taster and invites him to a private tasting.
Tucker checks on Oliver to see if he is ready to make his speech at the wine event. Oliver is drinking heavily and asks Tucker to join him. When Tucker declines, Oliver lashes out uncharacteristically, insulting Tucker and his father. Tucker finally breaks a wine bottle in anger but accidentally cuts his hand, a possibly life threatening injury for a hemophiliac. Luckily, Hank is still there and quickly dresses the wound.
In the barrel room, Evan continues to correctly guess the wine flavors. Divya is suspicious that Kim is not tasting as well and Kim reveals that she cannot taste anything. She says she might have an AVM, an abnormal connection between an artery and vein, because she has had one before. The treatment for her previous AVM gave her an amazing tasting ability. Divya says she needs a CT scan immediately, even before her insurance covers her.
Hank runs into Eddie at the wine tasting and Eddie asks about the photo he gave to Evan to show Hank. Eddie hoped it would trigger memories of a happier time between the three of them. For Hank, it triggered an unpleasant memory of when his father had him help steal their car back from an impound lot when he was just a boy. Divya shows up to talk to Hank about Kim and her headaches. She says she is taking Kim to Hamptons Heritage for a CT scan.
Hank and Tucker are talking before Oliver's speech and Hank is trying to reassure Tucker that he has a lot going for him, even if he has been disinherited. Hank is interrupted by Oliver's parents introducing their son for his speech. Hank notices the difference between the parents skin tones and Oliver's and has an epiphany about what might be wrong with Oliver. He calls to check the blood work and it confirms his suspicion of Addison's disease, a problem with the adrenal glands. They rush off to find Oliver only to find he has accidentally fallen into one of the large wine vats, where he had been hiding before his speech.
At the hospital for Kim's CT scan, Evan is being overly protective of Divya, who he thinks is pregnant. Divya tells him she bought the test kit for someone else and looks at Jill, who is administering the CT scan. Evan ask if he is going to be an uncle, and Divya tells him no one is pregnant when an idea occurs to her that Kim might be pregnant. Her headaches are a result of dehydration from the pregnancy.
Tucker leaps into the vat to help Oliver who is unconscious, but he passes out too because the fermentation process makes carbon dioxide which settles in the bottom of the tank. Eddie arrives to help and he and Hank rig a fan for get fresh air and a pulley to extract the boys. Tucker is fine but Oliver is not as he is not breathing properly and turning cyanotic from an obstruction. Hank needs to intibate but his bag is with Divya. Hank uses some copper tubing to pierce Oliver's throat and a piece a wire to pull some plastic tubing into his throat which allows him to breathe.
Hank has a moment with his Dad when he thanks him, saying he could not have saved the boys without him. Later while speaking with Tucker, he reveals that is was only a one time only thing. Tucker tells him he misunderstood the disinheritance issue. It was not Tucker but his father who was disinherited, and Tucker has been put in charge of everything, including his dad's allowance. Hank remarks how large a responsibility that is for a seventeen year old, but if anyone can do it, Tucker can.