When Stan recommends that Millie use physical fitness as an outlet for her emotions, she goes the distance, and creates a full gym in her apartment, and makes it open to the public. Taylor's fashion sense comes in question, and he goes too far in the wrong direction to prove Joyce wrong.

Crystal returns to work after having her baby, and immediately begins using Millie to get her work chores done. Stan becomes the hit of a pottery class that he and Anna are taking together, causing Anna to become a green-eyed monster; adding Taylor into the mix only makes things worse.

Stan tries to teach Millie how to be successful at losing when she's nominated for a Literary Award. Taylor shows Joyce a thing or two about schmoozing a potential client while Anna and Crystal spend the evening over-embellishing stories about their lives to strangers.

Stan comes to Millie's aid when she gets in trouble with her condo council. At Haddison House, Joyce promises to look at some of Taylor's clients if he promises to find someone to fix her dying plants.

Lewis makes a come-back into Millie's life and beats her at pool, so Millie takes some lessons in order to once again best Lewis. Joyce leaves the members of her car pool stunned by her driving skills, or lack thereof, and Stan unwillingly becomes involved in the situation.

Upon finding out that her condo unit comes with a storage locker, Millie decides to put it to good use by turning it into a clubhouse. Stan joins the club, but his intentions are less than honest; he intends to infiltrate the club and take it down from within. Joyce and Anna have a job on their hands when they try to stop Taylor from turning a profit from his new scheme of 'touching for tips.'

A problematic director sends Taylor and Millie's TV commercial into a tail-spin; Stan turns to Joyce for financial advice for Anna's plant business, but isn't happy when Joyce begins to mentor Anna.

Millie becomes disillusioned after not being thanked for returning a lost wallet and Stan tries to convince her that doing a good deed is its own reward. Over at Haddison House, Crystal stocks up on Joyce's favourite snack to prevent her from turning into a total witch and Taylor wrangles Anna into helping him buy a bobblehead online.

Millie decides that she'll only be truly appreciated after she's gone, and so wants to have her funeral now, so that she can see just how much she'll be missed. Stan tries to assist Crystal and her boyfriend with their new status as parents, but winds up babysitting instead of life coaching.

Millie wreaks havoc on Haddison House when Joyce makes her work in the office until her latest manuscript is finished. Stan enlists Taylor's help in proving to Anna that he has good fashion sense.

Stan accompanies Millie on a mission to give a young fan an autograph. Joyce and Taylor negotiate Millie's contract, and Anna and Crystal see this as a golden opportunity to mess with Taylor's head.

In the Season 2 premiere, a trip to Hollywood is in order for Millie, Stan and Taylor to investigate some options for a Grumpaloo movie. Back at Haddison House, Joyce uses Anna and Crystal as guinea pigs to test homemade skin care products.

After causing a public disturbance at a coffee shop, Millie Upton seeks out help from Stan Dirko, an inexperienced but enthusiastic life coach. In spite of his ineptitude, Stan manages to gain Millie's trust as a client. Meanwhile, Joyce, a work associate of Millie's, threatens to cancel an important event unless Millie finds the help she needs.

Joyce books Millie on her favourite daytime talk show but soon regrets her decision when Millie speaks before thinking. Much to Anna's chagrin, Stan takes her on a camping trip where she has to deal with Stan's lack of wilderness skills.

Stan attempts to analyze Millie's dreams but he grows concerned when they depict him in a negative light. Joyce is nervous when Taylor signs her uncle to be the first client at his new talent agency.

Casting the right reader for a spoken version of the Grumpaloo books pushes Millie to the breaking point; Taylor finds a way to convince the Haddison House employees that Joyce is behind his plans to have them fund his purchase of a leather jacket.