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. 

As Kim decides to take classes at Bill's college and date one of his star students, Bill must walk the line between teacher and dad. Dean and his friends join the football team where Dean finds himself in a tricky situation.