Evan barges in on a private moment between Hank and Jill to announce a new client, instantly killing the mood and derailing yet another date. At least the prospective clients are from old (and new) money and own a private island. The wife, Claire Grant, is due to give birth to her first child in three weeks, yet she insists on holding the annual family reunion with her sister on Grant's Island, which is only accessible by helicopter. Claire agrees to a small concession to her concerned husband Rob by allowing Hank to come along as a precaution. But what Rob doesn't know is that Claire is planning to give birth on her beloved family island - and she wants Hank to induce her labor.
Despite the Grant family's desire for an intimate family gathering, Evan manages to get himself invited by billing himself as a "manny" to care for Claire's nieces and nephew. Evan's hopes for a glamorous getaway are dashed when he sees how old-school and low-tech the house is. And since there's no cell service and the satellite phone is on the blink, Hank can't call to cancel his make-up date with Jill or to give her an answer about another proposition she made to him the night before: a job in the ER at Hamptons Heritage Hospital.
Meanwhile, Divya is holding down the fort on the mainland, but since she can't reach Hank, she finds herself flying solo in the dark. When she responds to a stray text message from Hank to follow up on a patient, she doesn't realize she's actually showing up for Hank's aborted date with Jill. The awkward situation becomes tense when Divya learns that Jill has offered Hank a job, which could mean the end of HankMed before it has even begun.