Jane Widen just turned 30 and her life is a mess! She's lost her job, her boyfriend, and her dog. Now Jane has no idea what she wants to do with her life. As if things couldn't get worse, there comes news of the sudden death of her Grandmother Madge. Now Jane must console her dear grandfather Billy, alone after 60 years of marriage.
Jane and her grandfather embark on a journey of healing together. Jane begins to pick up the pieces of her life and rediscovers who she wants to be, as her grandfather recalls how he met his wife Madge as the famous lounge singer Billy Cascade.