It seems the Hamptons don't agree with Queens transplant Jim 'Mac' MacIntyre. Though locals - including Jill and Hank - are lining up for the chef's addictive lobster mac 'n' cheese, Mac's been having some bad luck since he and his orange food truck arrived in town: first he and his truck get sideswiped in a hit and run, and now he and his new wife are having marital issues. Hank and Divya soon find themselves landing square in the middle of those issues when Mac's wife Donna calls them in to treat her injured ankle. While tending to Donna, Hank and Divya can't help but notice Mac's increasingly odd behavior, and begin to worry that there's something dangerous going on with this troubled couple.
And as it turns out, Donna and Mac aren't the only Hamptons residents facing both medical and relationship problems. Hank's newest clients, young heiress Paige and her much-older boyfriend Graham, are also in need of help from the HankMed team. As Hank attempts to treat Graham's mysterious vision problems, Evan gets drafted by Paige - who doesn't want her parents to know the truth about Graham's age - to act as her stand-in boyfriend.
While Evan undergoes his "faux beau" makeover and struggles with his growing feelings for Paige, Hank and Divya struggle to solve the mysteries behind their patients' bizarre symptoms. Meanwhile Divya's reemerging doubts about her future with Raj, Hank's burgeoning relationship with Emily Peck, and a surprising business proposition from Jill could mean some new complications - and uncomfortable moments - for the HankMed team. But as Hank's patient Graham would say, comfort's overrated.