Rachael is in Martha's Vineyard with John's family and chatting with his sister in law, Heather Woodbridge (and her little daughter Hadley!). They chat east coast wealth, how Heather met John's brother William and fell in love fast, and the girls recap the latest episode of Real Housewives of New York. They dive into the woes of parenting and how Heather gave wine to her children's teachers as gifts.