On the season premiere, Jann decides to take back control of her life and career, starting with hiring a personal assistant.

When Jann’s record label refuses to help her make a new album, she vows to find another way.

Jann surprises everyone by going on a date with someone new: a much younger man.

Jann, Nate, Max, and Dave go on a romantic mountain getaway, but Max has a problem with Jann’s new boyfriend.

An eccentric wealthy couple offers Jann the money to fund her new album in exchange for promoting their gender reveal company.

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.

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