Jill (Jill Flint) is the beautiful administrator at the local hospital, Hamptons Heritage. The Hamptons native is down-to-earth and completely unimpressed by the rich summer residents and the superficial lives they lead. But her constant challenge is that the hospital, the only one in the Hamptons, has a terrible reputation among the wealthy, which is one reason the market for Concierge Doctors has grown. Still, there are plenty of "ordinary folk" in the Hamptons who need urgent medical care and Jill has made it her mission to make sure they get it-whether it be at the hospital or a free clinic she has opened with Hank's help and Boris's money.
The return of Jill's not-yet-ex-husband Charlie throws a wrench into the romantic works between Jill and Hank. Even after Charlie takes off once again, Hank and Jill decide to keep their relationship platonic and professional--that is until Dr. Emily Peck, an overly headstrong yet sexy concierge doctor who's competing with HankMed, comes onto the scene and turns Hank's head. But just when Jill and Hank begin rekindling their romance, Jill gets a job offer of a lifetime...in South America.
After much thought, Jill breaks things off with Hank so she can go to Uruguay as planned. Then pro-golfer Jack returns and sets his sights on Jill, making Jill more confused about her future. But a relationship with Jack is not meant to be...and now Jill is faced with making a decision once and for all.