Overview: On the season premiere, Jann decides to take back control of her life and career, starting with hiring a personal assistant.
Overview: When Jann’s record label refuses to help her make a new album, she vows to find another way.
Overview: Jann and Max spy on their mother Nora as she goes on a date.
Overview: Jann surprises everyone by going on a date with someone new: a much younger man.
Overview: Jann, Nate, Max, and Dave go on a romantic mountain getaway, but Max has a problem with Jann’s new boyfriend.
Overview: An eccentric wealthy couple offers Jann the money to fund her new album in exchange for promoting their gender reveal company.
Overview: Jann’s crowdfunding campaign for her new album reaches its goal, thanks to an $80,000 donation from a mysterious anonymous donor. Jann, determined to figure out who donated the money, enlists Trey to help her investigate her “suspects,” which culminates in crashing a funeral. But the biggest revelation comes while investigating Jann’s ex-girlfriend — as it’s clear Cynthia is truly moving on without Jann.