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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.

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 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.

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.

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 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.

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.

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.

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.

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.

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.