It’s the summer of 1969, and Dean and Bill are experiencing new walks of life in New York City where Dean has tagged along for Bill’s career-making songwriting gig. Back in Montgomery, Lilian’s infamous sister, Jackie, pays a memorable visit.
Torn between his secret relationship with Keisa and his friendship with Broderick, Dean turns to Jackie for advice. Meanwhile, after her latest run-in with the law, Jackie decides to turn over a new leaf.