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.

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.

Stan helps Millie expand her social circle by introducing her to speed dating but Millie takes the "7 minute date" concept to a whole new level. Joyce and Crystal can't decide on the budget when they throw a party at Haddison House.

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.

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.

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.

Stan is concerned with Millie's competitiveness when she and Taylor go head to head in a hot food eating rivalry. Meanwhile, Joyce, who isn't a good judge of fantasy-romance manuscripts, passes the job of picking their next book over to Crystal – a self-proclaimed expert in the genre.

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.

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.

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.

Millie finds that indoor hockey isn't all it's cracked up to be when a wayward puck destroys her ant farm; she bunks with Stan and Anna, causing some marital stress. Joyce needs to replace Crystal, and with Taylor's help, finds the ideal receptionist.

When Millie hires Crystal to re-decorate her condo she gets into another tiff with her neighbour Lewis and vows to beat him at his own persnickety game. Stan attempts to help Joyce with one of her issues in order to prove that he's capable of being Millie's life coach.

Stan is in the doghouse with Anna after refusing to accept an extravagant anniversary gift from Millie. Meanwhile, Joyce and Taylor have to deal with a head shop that's selling illegal Grumpaloo merchandise and Crystal is up to her neck in Millie's fan mail.

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.

Millie holds a dinner party, but shocks her guests with the menu selection; Joyce and Anna suggest that she cleanse her system, and offer to go through the process with her. Taylor's womanizing gets him into trouble at the office, and he turns to Stan for help; Stan finds that helping Taylor teaches him more about himself than he wanted to know.

Taylor is having some personal issues so Millie happily recommends that he see Stan. But she soon realizes that the more time Stan spends with Taylor the less he spends with her. Joyce has to find a model for an upcoming book cover and her choice to use Anna does not sit well with Crystal.

After the top mystery author at Haddison House casts aspersions on Millie's Grumpaloo books, she decides to fully explore her authorship by writing a novel. Turning to Stan for help with this process, she finds that Anna is a better guide than her life coach. Taylor learns some new lessons in how to be sexy when he has an encounter with an older woman.

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.'

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.

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 causes an uproar once again by insulting a famous pooch at a public event. Anna tries to redecorate on a budget, but finds it's hard to do, as one thing leads to another. Stan has the difficult task of getting Taylor to help discard the old apartment's old furniture without calling in a 'friend favour'.

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.

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.

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.