Jeff, Britta and Annie help Dean Pelton recruit a wealthy potential student; Abed starts a fraternity; Troy and Shirley attend a physical education class.
As the hospital continues to make positive changes under the new management, the doctors begin to realize that owning a hospital comes with its own set of problems and responsibilities. Meanwhile, Meredith worries about the wellbeing of her unborn baby, Callie and Arizona try to get the spark back in their relationship, and Alex gives Jo‘s new boyfriend a run for his money.
Olivia finds herself in the middle of a media storm, but this time she's on the opposing side of the oval office when Fitz's pick for Supreme Court Justice is caught in a torrid affair with Liv's new client, high-powered CEO Sarah Stanner. Meanwhile, Olivia and Jake continue their flirtatious relationship, while Huck takes Quinn under his wing and Harrison and Abby try to figure out where they stand with their friendship. Back in the White House, Cyrus and Mellie continue to fight for Fitz's attention, but someone else may already have it.
Realizing that Elena needs some time away from Mystic Falls, Damon takes her to New York City, where he lived and partied hard in the 1970s. When Rebekah also shows up in New York, she’s impressed with Elena’s secret agenda. Flashbacks reveal Damon’s hedonistic life in the underground club scene and a complicated encounter with Lexi. Meanwhile, Caroline and Stefan try to convince Klaus that it would be in his own best interest to help them track Silas down, and Bonnie struggles to keep her grasp on reality and do the right thing.