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- A teenage Robin Hood steals for a needy cause in this updated tale of doing the wrong thing for the right reason.
- Twenty-four year old Tanya, who's lived on her own since she was seventeen, is a $33,000 per annum income cosmetician at a drug store. She uses the excuse of being in the fashion business to splurge on herself to look good, and further to live the high end life. She believes she deserves what she spends on herself. She treats her boyfriend, Jamal, like her sugar daddy, he who moved out of their shared accommodation because of it. Her friends don't expect anything from Tanya when they go out because they know she will never offer to pay. If she doesn't have enough money to spend on her indulgences, she sponges off her family, which has placed her grandmother Verna, who lives off a fixed pension, in a difficult financial situation. Her father has already cut her off. A diva, she uses emotional blackmail, often throwing temper tantrums or giving the cold shoulder, to get what she wants. She had in the back of her mind that she would rack up the debt, which she is unaware sits at $30,000, and then declare bankruptcy to make it all go away. Gail wants Tanya to see what it's like to live on her grandmother's income for a month - about $1,000 less a month than Tanya's own income - which has to cover everything, including debt repayment specifically to Verna. Gail makes Tanya go through a goal setting exercise for something that she would like to achieve in her life. Gail provides Tanya with a stylist to show her how to maximize the use of her existing wardrobe. Because Tanya still wants to spend on indulgences, Gail makes her calculate the number of work hours to get enough disposable income to buy each item. Tanya has to pay back Verna in services as well as money. And Gail places Tanya in a situation of temptation to see if she falls back into old habits. But it's Tanya's timeliness in the initial meeting with Gail which sets the tone for Tanya's journey.
- Early thirty-somethings Karla and Greg are engaged, but they have totally different views of money and debt which could threaten the marriage. Karla does not believe in consumer debt, she spending on items she can afford and on which she pays cash. As such, all her "toys" are paid for and she is consumer debt free. Greg, on the other hand, had racked up a debt of $33,000 before Karla found out about his secret gambling life being addicted to slot machines. He has since moved to poker. Because Karla feels she can't trust Greg concerning money, she at this point refuses to have any joint financial accounts with him until he becomes debt-free (it currently sitting at $23,000) and remains debt-free for some time. As such, their relationship currently is more like a mother chastising a son she doesn't trust than as man and wife. Greg still wants to be able to spend his money as he sees fit, gambling being his entertainment. Despite the money issue being Greg's sole doing, Gail has to get them to: work together as a team in managing what will be their household finances, while they deal with their individual money issues, Greg's which includes his current debt that requires a bigger income to pay off timely than he is currently earning; shift the power balance of their relationship, especially when it comes to potential family issues; find less expensive alternatives to gambling as entertainment they can do together; and rebuild the trust that Karla currently does not feel with Greg. Gail issues one major make it or break it rule right at the beginning which sets the tone of the process and perhaps for Karla and Greg's future.
- With special guests Dextrous One and actor/comic Scott Thompson.