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- Early thirty-somethings Jillian and Orson, who have two toddlers, earn a combined income of $70,000 annually, which does not go very far for a family of four in the expensive city where they live. They were already in debt individually when they came together. Jillian spends on little things, such as going out for lunch with coworkers leaving the brown bag lunch Orson made for her sitting uneaten in the fridge, which over time adds up. Orson works at a low paying job he doesn't like, but feels he needs it to support his family. Jillian has a large extended family, individuals from which drop by frequently and unannounced which also generally includes staying for dinner. Some have even lived with them at times, with Jillian and Orson footing the bill, which has caused some unspoken friction between Orson and everyone else. Jillian, who solely manages their finances, sometimes has to make the decision whether to pay daycare or rent. They dream about buying a house someday, which to them seems unattainable. They are currently $23,000 in debt, most of it sitting on high interest credit cards, with not much to show for it. Gail wants the two to reverse household roles to see their lives from the other's perspective. She wants there to be even more balance in their household which includes Jillian's family giving back for all they have taken thus far. She wants Orson to be more motivated in exploring options for higher paying jobs. She shows them if home ownership can be in their future. And she has to get them working together as a couple.
- Evelyn and Andy live off Andy's annual income of $128,000, as Evelyn is the stay at home housewife and mom to two infant children. Despite their comfortable income, they still have $73,000 of consumer debt, and no house of their own. They used to own a house, but moved across the country twice, the first move to Calgary which led to Evelyn feeling isolated and like they were starting all over again, the issues at the core of her emotional spending, especially on online makeup (as she feels stuck at home with nothing else to do) and spa treatments. Andy can't understand why they shouldn't be able to afford the luxuries in life, such as the $4,000 projector television. When Evelyn asks Andy, the sole household financial manager, about the financial issues, Andy accuses her of not trusting him. Gail wants: Andy to investigate disability and life insurance options; Evelyn to find social options for her and the kids outside of the house, most specifically with other parents and their kids; Evelyn to be involved in the household money management; them to set five year goals and how they will achieve them; and to find staycation activities instead of the pricey vacations they have been taking, which were all in an effort to save their relationship.
- 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.