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- Three single guys share their personal problems as well as a loft apartment.
- 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.