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- Amanda is involved with a weekend acting workshop but her plans must change when her mother asks her to babysit her boyfriend's young daughter Pheobe. Fearing that she will be penalized for missing the workshop, Amanda changes things around to accommodate both the workshop and babysitting. Unfortunately, her plans don't go as expected and Amanda must face the consequences.
- Deanna calls in Gail to deal with her fiancé, James, whose money management she wants dealt with before they get married. Deanna even states that James' money management problem may be a deal breaker in them actually getting married. They both would like to be full time actors, but because they are still in the struggling phase in that aspect, they work part-time in the service and retail industries, bringing in little money to live. As such, they live in the basement of Deanna's parents' house, where they will stay until they get on their feet financially. Part of Deanna's concern over the money is that she wants a big wedding typical of her Italian family, and shortly after getting married wants to start a family. James' primary money issue is that he lives for the here and now, not watching at all how much money he spends or to where it goes. Beyond giving them both a financial diary so that they can keep track of how much money comes in and how much goes out, Gail has to get them on the same page for their immediate life goals so that they can plan on how to achieve them. For James specifically, Gail wants him to understand the need to work at something to bring in money to live, while being more proactive in selling himself for those acting jobs. But in looking at their finances, Gail finds that Deanna is a worse culprit with money than James. The big issue for the couple is if it is worth going further into debt to pay for the "big party" aka the lavish wedding when they already have other debts to pay off.
- Roy calls in Gail to deal with his husband, Kristoffer, most specifically the problem of his constant spending for things for his magic show business, without thoughts of the money itself. Most of that money is earned by retired accountant Roy, who gets $62,000 annually as a work pension and who had minimal consumer debt before getting together with Kris, that consumer debt now over $100,000 primarily from Kris' spending. Kris brings in approximately $10,000 annually, most of that being an allowance from his mother. Kris, who usually spends before telling Roy if he tells Roy at all, justifies it all by the old adage of needing to spend money to make money, namely the expenditures allow for a wider array of shows to be produced with the thought that he will get more bookings overall. Gail, who considers the business more of a hobby than a true business, wants them to draft a business plan, something that Kris had never done in his seeming unfettered access to other peoples' money without question. As part of that plan is to take stock of Kris' current mostly never used inventory of props, Gail feels it is a good opportunity also for Roy to review his own stored items as the specific task at hand is not only to justify what Kris should keep of that inventory, but to downsize from two storage lockers - currently "his" and "his" - into one. Gail also wants Roy to demonstrate that he understands the errors of his spending ways by putting on a magic show on that theme, and to do what most other struggling artists do, namely get a job that pays his fair share of the household the bills, having a regular source of earned income which Kris has never done despite being forty-three.