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- An offer to judge a prestigious beauty pageant in Thailand prompts Jenna into making a fateful choice, one that could end up damaging her relationships with several close friends. A chance to mentor a young transgendered model thinking of reassignment surgery forces Jenna to take a hard look at her life choices.
- Jenna and her new publicist Vanessa hit the Big Apple for some important business meetings and a photo shoot with PETA - a shoot that may be more risqué than even Jenna can handle. But Vanessa soon discovers that for all her effort to get opportunity knocking at Jenna's door, her new celebrity client may be too busy partying to answer. It's going to take all of Vanessa's limited patience to get Jenna in line.
- Jenna's putting final touches on her new apartment when she gets the news of a lifetime -a lucrative offer from Playboy. Everyone is excited - everyone, that is, except for Jenna. While she weighs the pros and cons of showing her "goodies" to the world, Dajana and a friend try to pull Jenna out of her new town dating slump by setting her up on a blind date. What Dajana doesn't know is that for Jenna, the only thing more frightening than posing nude is going out with someone she's never met.
- Jenna's offered a chance to audition for an action film - all she needs to do is convince the producers that she actually knows anything guns and violence. To get 'combat ready' Jenna goes on an action-star crash course that may have more crashing in it than Jenna's prepared for. Meanwhile, Angela returns to make a new home close to her favorite cousin, which could prove to be the worst thing that ever happened to Jenna.
- They say Hollywood is where big dreams go to die, and Jenna may be about to discover this for herself. From the moment she lands in LA with Vanessa, Jenna's plans start to unravel, putting her shot at a film career in serious doubt
- The Thicke's PG-13 dream of a little house on the beach turns into an NC-17 nightmare when they realize their new neighbor - an old 'friend' - is working on an "art project" that would be illegal in some countries. Jon Dore guest stars.
- People remember Jenna Talackova best as the transgendered beauty queen who was kicked out of the Miss Universe Pageant for not being born a female. For them, Jenna's eventual re-entry into the competition was the end of the story, but for Jenna it's only the beginning. She's ready to use her new celebrity status to launch her career, but as Jenna learns fairly quickly sometimes fame can be a double-edged sword.
- Alan and Tanya talk babies. Well, at least they try to, but the arrival of an incompetent intern proves distracting.
- One of Alan and Tanya's longstanding employees quits. Meanwhile, Carter gets a job.
- Alan allows Carter to throw a house party, but he comes to regret his decision.
- Alan and Carter go on a citywide manhunt when they suspect someone has stolen Alan's cellphone. Tanya's desire for a mirror in her bedroom pushes her into an unwise bet with Alan. Wayne Brady guest stars.
- Carter gets surprised by an anonymous invitation to a high school prom - but who it's from is an even bigger surprise. Alan makes the misguided decision of picking a fight with Tanya over whose renovation project should take priority. Lance Bass guest stars.
- Alan, Tanya, and Carter are each forced to speak out against injustices in their family. For Carter, it's the new security cameras Alan has aimed directly at his room. For Alan, it's a friend's novel attempt to cheat at golf but for Tanya, it's Alan's habit of taking her on "romantic getaways" to celebrity golf tournaments that are anything but romantic. Russell Peters guest stars.
- Both Alan and Carter are forced to confront things they'd rather not think about. For Alan, it's the amount of germs in their house, and for Carter it's a tattoo anywhere near Tanya's swimsuit area.
- The Thickes are forced to take desperate measures when their war with a noisy neighbor escalates. Robin extends a special invitation to Carter, which Carter completely misinterprets. Robin Thicke guest stars.
- Alan thinks about hanging up his spurs after his new gig as a spokesman for "age-appropriate" products has him contemplating his own morality. Tanya gets so caught up with her upcoming kitchen renovation that she almost forgets about Alan's 68th birthday. Cedric The Entertainer guest stars.
- Alan's dream of becoming the "Guacamole King" of his community is thwarted when a visiting friend makes a public spectacle of offending everybody in town. Gilbert Gottfried guest stars.
- Alan's efforts to land an insanely profitable gig as spokesman for a native casino hits a snag when he discovers he must first prove his native ancestry (no biggie, except for he has none). Carter's preparations for his forthcoming Canadian citizenship test are hampered by some highly unusual anxiety dreams. Alex Trebek guest stars.
- To escape their seemingly endless kitchen renovation, Alan takes Tanya away on a weekend road trip and quickly re-discovers his pathological hatred of California traffic. Carter is less than thrilled to find out Alan has gotten him a babysitter, until he meets the babysitter. Kato Kaelin guest stars.
- A failure to communicate ends with Alan and Tanya double-booking events at the ranch for the same day. Carter and Alan decide to build a storage room for a friend, and they refuse to let anything get in their way, including the fact that they've never built a room anywhere, for anyone, at any time.
- A family friend makes an offer to Alan that he should probably refuse. Tanya's life turns into a fight scene from a gang movie after her war with a cyber-bully suddenly jumps off of Twitter and into the real world. Dave Foley and Wayne Brady guest stars.
- Alan pushes his luck when he creates a 'bucket list' of things he thinks Tanya wants to do most for her 40th birthday. Cat Cora and Lou Ferrigno guest stars.
- In Illusions of Grandeur, up-and-coming street magician, Zack Mirza, strives to take his magic skills to the next level. In this new docu-series, Zack's on a quest to become one of the best-- in the same league as Blaine, Copperfield and Houdini. But first he must rise to the challenge of this epic journey as he travels to twelve cities in twelve weeks, performing dozens of brand new illusions. On this magic pilgrimage, Zack walks in the footsteps of the greats and brings his brand of street magic to cities like Toronto, New York, Austin, Las Vegas and Detroit. In each city, Zack focuses on a different style of magic like mentalism, escapes, or card magic. He wows locals with tricks on the street, and digs deep into each city's magic culture. Drawing inspiration from history's greatest magicians, Zack performs all new effects and puts his own spin on classic illusions. All of Zack's magic is performed live in front of real people, without the use of camera tricks, leaving viewers captivated by the genuine, larger-than-life reactions.
- Money morons are a leading cause of ruined relationships. As such, financial advisor Gail Vaz-Oxlade, in an amalgam of what she did for couples of various stripes in Til Debt Do U$ Part (2005) and for divas and divos in Prince$$ (2010), undertakes an intervention on behalf one of half of a couple who believes the other half of that couple is leading them into financial ruin which may in turn result in the imminent break-up of the relationship. Gail reviews the money management within the household to see what needs to be done to fix the financial problem. Beyond the keeping of a financial diary, Gail issues a series of tasks, which, depending upon their completion to Gail's satisfaction, will lead to Gail giving them up to $10,000 to help them get back on their financial way at the end of her time with them. However, Gail often finds that the story is not as lopsided as it is initially presented to be to her by the intervening one of the couple, that person who is often as much at fault if not more so in the financial problems.
- To help get her mind off recent setbacks, Jenna decides to get her party on in Las Vegas, bringing Dajana and Angela along for the ride. But a simple weekend of drinking and gambling gets complicated when a kind gesture exposes the deep cracks in Jenna's relationship with Angela.
- Alan takes Carter to visit his brother, Robin, on the road, in hopes he'll learn that being a superstar is about more than just limos and champagne. Tanya takes on far more than she had planned on, when she agrees to rescue a homeless animal.
- Alan faces a major dilemma when the annual charity hockey tournament, he and Carter never miss, falls on the same weekend as Tanya's 20th high school reunion. America's favorite dad is forced to reassess his priorities, and quickly realizes the biggest challenge in being a husband and father is when you can't be both at the same time.
- Alan is inducted into the Canadian Walk of Fame and Tanya has to deal with his overinflated ego.
- Alan's approached about being the new "spokestud" for a male enhancement pill, something he's quick to dismiss until he finds out his rival, David Hasselhoff, is up for the same job. It's up to Tanya to remind Alan that private parts are private for a reason.
- Alan tries to get Carter interested in attending his alma mater; Tanya considers having a baby.
- Troubles in her family leave Tanya feeling depressed, prompting Alan to come up with a novel and possibly humiliating way to cheer her up. Tanya gets useful advice from a man who's not afraid to let it all hang out.
- After his agent approaches him about rebooting the Growing Pains (1985) franchise as a parenting manual, Alan approaches John Stamos to play the part of son Mike Seaver. Alan gets shot down and decides, the best way to get the old cast back together and film them, is to not tell them they're being filmed.
- It's the Thicke Family cottage weekend, and Alan is determined to maximize the fun by keeping his family to a tight schedule that nobody likes. Back at the ranch, Tanya decides to cure her hot-blooded Latin brother, Kenny Callau, of his overly flirty ways.
- Alan and Tanya come to an important realization about marriage, as they attempt to spend more time together.
- Alan and Tanya's arrangements for their ranch manager's wedding are jeopardized when the Elvis impersonator they fired from the festivities decides to crash the party.
- 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.
- Laura calls in Gail to deal with her husband, Sean, who is the person within their household who handles the money issues, such as paying the bills. They both earn a decent wage which should make managing their household finances easy if done properly and within their means. The wake-up call for Laura that there is a problem with how Sean handles the household money is when an error he made led to a $10,000 income tax bill. Upon closer investigation, Gail does find that Sean is a money moron, but not for the reasons Laura stated in their meeting prior to them ambushing Sean. Beyond the income tax problem, which Sean readily admits was his fault and thus is his responsibility to fix (i.e. pay), Gail finds that Sean and Laura do not communicate with each other properly about their finances, with Sean shutting down anytime there is a confrontation, leading to Laura doing whatever she wants unilaterally, which is shop as a hobby. While Laura complains about the amount of money Sean pours into his beater of a car and the television with all the bells and whistles (which in reality he does not pour as much money into as she guesstimates), she in turn spends uncontrollably on clothes and home decor items, the latter with little to show for in their house in she not wanting to do anything with the items in her indecisiveness in not wanting to decorate in a way she will regret later. And although they both earn a relative equivalent to each other, Sean does most of the heavy lifting financially when it comes to their needs, especially for their shelter. Gail wants this couple to start communicating with each other, a symbolic task being to decorate one of their rooms to both their satisfaction, mostly with things they have already purchased, with all other items purchased that haven't been used to be sold or returned. Gail also provides them with a life coach so that they can get on the same page with their goals in life, and with that the financial obligations they have jointly.
- Josh calls in Gail to deal with his wife, Kat, with who he is constantly arguing over her spending. The only thing Josh and Kat both seem to agree on with regard to their financial situation is that Kat should be a stay-at-home mom, their son now an infant, and that she should never have to return to work. She works part-time as a dog walker, bringing in $8,000 per annum, which is her spending money. Confronted, Kat does recognize that she is a money moron, she who made some effort in consolidating debt to get it to a manageable level only to get another credit source to increase that debt. She also spends primarily and impulsively on things for their son, he now having outgrown many of those clothes and toys. As such, Gail would like Kat to organize a toy/clothes swap with other parents not only to get those things she needs for him, but to declutter their house of the things he no longer needs which are of value to others. However, in reviewing this situation, Gail finds that Josh is a large part of the problem in their household. He works freelance as a massage therapist and running coach, his on average 28 hours of work per week bringing in an annual income of $32,000. He enjoys this somewhat carefree work life, and is resistant either to make a concerted effort to work more - new clients which he only gets on referrals from existing clients - or find other sources of income to support the family. He also spends more time looking after their dogs (4 hours per day of dedicated time) than he does with their son (2 hours per day of dedicated time), the latter he sees as Kat's responsibility. He defends his free time as needing to keep in shape/train to maintain his ability to do his work, and in being a responsible dog owner. Josh pays the rent, but Kat looks after everything else financially for the household. With their arguments about finances, Josh sees it as a necessity as he believes Kat doesn't listen to him when he speaks calmly, while Josh walks away whenever Kat argues back. They both see the current situation as being unsustainable, their marriage on the breaking point if something doesn't change.
- Lisetty calls in Gail to deal with her husband of three years, Ryan. What concerns Lisetty, now more than ever, is that Ryan, who works as an independent contractor (i.e. he pedals his business to client companies), has never understood the complexities of tax laws affecting small business owners like himself, which has dug him into an income tax hole - with another tax year end approaching - with their first baby on its way. On top of the tax debt, Ryan spends based on his revenue (on average $90,000 a year) instead of accounting for expenses, including the relatively large year to year tax burden. A large part of that spending is a $15-20 lunch out every day, he who has not brown bagged a lunch in five years. In addition, Ryan purchased a revenue property with a friend, for which Lisetty cosigned a loan despite not legally being part owner of the house. After the loan was signed, Ryan unilaterally took out additional money on the loan, which shows Lisetty that he may not be a responsible parent if he is focused more on his own financial needs than theirs as a family. What Lisetty is unaware of is that she, as the cosigner, is responsible for the loan if he defaults on it. What Gail sees in Ryan and Lisetty as a couple is that Ryan handles all the household finances, shielding Lisetty from any of it in his belief that it is above her head, not realizing that he has made a mess in handling it on his own. Beyond giving Ryan the services of a tax consultant specializing in small business owners like himself and impressing on him the need to cut his spending (meaning no more lunches out), Gail wants Ryan to see that Lisetty should be involved in the financial management for the household. But Gail also wants Ryan to get a good view of life after the baby is born and how that truly will affect him in what he needs to do as a household provider and them as a couple in being responsible parents.
- Leah calls in Gail to deal with her fiancé, Will, the couple who have an infant daughter together. Leah and Will each earn approximately $30,000 per annum in their respective jobs. Leah's primary issue with Will is his frequent nights out with friends, which will easily cost him on average $100 per outing. An associated issue is that Will's time away leaves Leah to handle most of the work around the house, including the care of their daughter. Confronted by Gail and Leah, Will admits that he probably does spend more than he should in those nights out. But upon inspection of the spending within the household, Gail finds that Leah is the bigger moron. While Will handles paying most of the household needs, such as rent, Leah spends more on wants such as clothes and entertainment. The dynamic within the couple is that although they claim to talk about money and finances, they don't really in that they will allow the other to do what he/she wants in order to keep peace at the time. Gail also finds that they haven't really discussed in a meaningful manner their joint goals in life, including if and when they should have more children. The first task Gail has for them may be the biggest shock for them: getting rid of one of their two cars, that second vehicle which they cannot really afford on their incomes, with the result being one and/or the other adjusting to other means (such as public transit) to get around, especially for commuting. Gail sends them to a life coach, who plays a question and answer game to show them how close or far apart they are in their wants in life. Gail also wants them to switch places to balance out the roles, with Will tasked not only with the cooking and cleaning (the former which he professes not knowing how to do well) but the care and feeding of their daughter, and Leah tasked with budgeting to see how important her income is to the maintenance of their household finances.
- Anne calls in Gail to deal with her fiancé, Michael. Anne had previously called off their engagement before because of what she considers Michael's reckless spending, especially on his man toys. An example of that reckless spending is that Michael spends more on a monthly basis on his luxury sedan than he does on the mortgage on his house. To protect her own financial self and well-being, Anne purchased her own house during their break-up, which she is reluctant to part with because of not fully trusting Michael. Anne states that she will have no hesitation in breaking up with Michael again if he doesn't change his spending ways. Michael's debt is also despite he earning a good $100,000 living as a radio DJ. Gail tries to impress on Michael the difference between setting his house or his car as a main priority. Gail also wants him to redirect his energies into the wedding, primarily to walk a figurative mile in Anne's shoes to see what she is going through in terms of spending responsibly on what should be a joint goal. She also wants them to sit down and discuss rationally as opposed to emotionally what they are going to do in terms of their post-marriage living, the two houses which they don't need. This task may be more difficult for Anne as Michael's house carries the emotional baggage of the problems when they lived there together previously. On the flip side, Gail wants Anne to understand that Michael does not want his past spending problems to be constantly thrown in his face if problems arise in their relationship, this something Anne has done in the past in her mistrust.
- Courtney calls in Gail to deal with her husband, Dylan, the two who have been together for ten years. They have an infant son, Dason, who was a surprise in their lives. Dylan wants them to have another child, but Courtney is concerned that Dylan's reckless spending - on the surface on nights out with the boys specifically having meals at the bar, and on cigarettes - will prevent them not only providing for Dason but for that future child. Another hit of Dylan's sole doing had to do with his car insurance, which required his parents to bail him out financially. As such, Courtney wants to put her foot down in not getting pregnant unless Dylan changes his ways. She also fears that their financial issues may lead to them needing to split. Gail finds that what is happening in Courtney and Dylan's household is not all that it appears from Courtney's side. Although Courtney, who handles all the household finances, is dead on that Dylan spends on average $400 a month on those spur of the moment meals out - more than Dylan suspected - she is surprised to learn that Dylan has socked away some money, both as savings and in an education fund for Dason. Dylan's issue is that Courtney, who is a full time nursing student, has spent her working life on part-time jobs that neither he or she would ever consider careers. Despite she currently earning half what he does, they had made the decision to split the household expenses down the middle, thus he feels she hasn't held up to her end of the financial burden. Dylan however admits that he has little understanding of finances in general, his financial doings on an individual basis without looking at their household money on a comprehensive basis. Gail wants the couple to look at their money more holistically with Dylan taking more responsibility, which means either he hands over his paychecks to Courtney to pool their money for household bills, or Dylan will take charge of the paying of the bills. Gail wants Dylan to set long term budgets to deal with their debt, in combination with both going through a goal setting exercise to see if another baby truly is priority in their lives.
- Mike calls in Gail to deal with his fiancée, Kelly, who he believes spends too much money on her hobby of scrapbooking. Mike admits that he is afraid to confront Kelly about the issue on his own, largely out of circumstance. Kelly, a teacher, earns almost twice the amount of money he does as a call center employee. He at some point in time would love to get a higher education to earn more money, but life circumstances - he and a former partner having a child at a young age - have prevented him from being able to do so, his infant daughter who is in his custody. That fear is that Kelly has the financial power in their relationship, he being unable to provide for his daughter if Kelly were to leave. He also admits that his beef is somewhat "sour grapes" in the disparity in their financial situations. Regardless, they have a fifty-fifty split in household expenses, which leaves Mike with no disposable income and Kelly with it all within their relationship. Beyond believing the fifty-fifty split in household expenses inequitable, Gail, in reviewing the situation which includes getting Kelly's side of the story, sees the major issue between the two being a lack of effective communication. As they don't want to talk about their issues constructively, Mike generally sits on the couch playing video games on the television, while Kelly scrapbooks or goes out with her friends. As such, Gail believes they are acting more like roommates than a committed couple. Acting truly like a couple is the foundation of the change that needs to occur for them to get on a sound financial footing.
- Anthony calls in Gail to deal with his wife, Tamara, who he feels spends indiscriminately. They have a relatively low combined annual household income at just under $45,000 which is part of their financial issue. Beyond their household expenses, they made an agreement that she would only spend on things she needs for work as a hairdresser, which still seems to add up to a lot of beauty products. Part of Anthony's concern is providing for their infant daughter properly, they not wanting her to fall into the feeling of being poor like they both did when they were growing up. However, their financial situation does not stop them from dipping into their daughter's savings whenever they feel the need. Anthony also wants to have more children which will compound their financial problems unless something changes. Part of providing that security for their daughter is their want to own their own house instead of renting for their entire lives. Anthony seems to realize that he is not totally blameless, he often taking the easier path of going out for fast food instead of eating at home. Also, Tamara does all the finances for their household as the one with the greater natural aptitude in that area. In speaking to Tamara, Gail finds a somewhat defeatist attitude in that Tamara has always felt poor, and feels that nothing they will ever do will change that. Gail gives Tamara a choice with regard to certain issues to see where her true priorities lie. Gail also wants them to see what it will take to work toward their stated goals of a house and more kids, and whether the short term pleasures they currently spend on are worth forgoing those longer term goals.
- Tammy calls in Gail to deal with her husband, Rob, the two who are close to splitting if they cannot resolve their problems. They are parents with two preschool aged sons. Their current annual household income of approximately $74,000 is primarily from a military disability pension Rob earns, he who suffered brain damage which required two years of recuperation during which time he didn't work. It was then that Rob started to spend indiscriminately online, many purchases about which he now admits he feels guilt. Those purchases are what have largely sent them into debt. Rob also has a hobby business of keeping bees, a business which he says is revenue neutral. He does not consider the $25,000 truck he bought specifically for the business a business expense, as he paid cash using household money. Tammy manages the spending for the family and household, such as on groceries and items for the children. While Tammy no longer trusts Rob, Rob accuses Tammy of hiding away money, effectively accusing her of stealing. Both Rob and Tammy admit they want their marriage to work, acknowledge that it will take some fundamental changes, and hope that the disintegration of it is not past the point of no return. Gail is hoping more so than usual that the truth in terms of what is happening with the money will be an eye opener for both of them. Beyond means to spend their money more wisely - such as learning to cook which will reduce their household food budget - the challenges Gail issues and the assistance she provides is largely to try and restore measures of trust and cooperation in their day to day lives, the trust building including Rob walking a mile in Tammy's shoes.
- Alison calls in Gail to deal with the money management issues of her husband, Dan. Dan, who has always enjoyed the finer things in life and who likes to be generous to friends which often manifests itself in picking up the check in frequent meals out, lost his $80,000 per annum job shortly before he and Alison got married - something he postponed telling her in his want for her to have the wedding she wanted - that job which was replaced by a $30,000 per annum one. Alison, who has yet to start her teaching career, got pregnant shortly thereafter, she now six months into the pregnancy. Even with those added expenses and less income, Dan's spending did not change, the biggest bone of contention being a luxury sedan which Dan unilaterally purchased and that Alison does not think they can afford. They currently live with Dan's mother in her house rent free until they get back on their feet, this living arrangement which further places a strain on their young marriage. Alison is afraid that Dan, who has always been the reassuring one in their relationship, may talk a good talk but not do anything in a concrete fashion to deal with their financial problems. Beyond the spending diary which they are to keep, Gail wants Dan to sell the car, even if it means taking a loss on it. She also gives them $200 to carve out a small space in his mother's house for them including the baby, something which Alison was initially reluctant to do if only in making the living arrangement feel more permanent than she wanted. And she wants them to prepare a five year budget so that they will be on the same page for their medium term life goals.
- Celeste calls in Gail to deal with her husband, Mike, the two who were teenaged sweethearts and the other's first love. They are parents to an infant son. The problem in Celeste's mind is Mike's addiction to shopping in general, which has placed them deep in consumer debt (above and beyond their mortgage), and the resulting hoarding, the "stuff" which Mike keeps in their garage and two rooms in their house, all three which are packed to the brim with this stuff, mostly untouched and unused, with many of the individual items somewhat forgotten. Mike admits that he gets a warm feeling inside whenever he buys something. He also professes to place their son and Celeste as his first priority, which does not match his actions in that his indiscriminate spending has placed the family in financial risk. Gail is hoping that knowing the actual amount of their consumer debt and how fast it is increasing will open Mike's eyes to the extent of the problem and be one factor in Mike's rehabilitation to his addiction to shopping. As part of the problem is the hoarding, Gail provides the assistance of a professional organizer to help Mike organize the stuff: what can be kept, what can be resold, what should be donated to charity, and what should just be sent to the recycle or trash. Gail also realizes that Mike needs to redirect his energies from shopping to something that is more productive for them as a family. But Celeste also realizes that although Gail has forced Mike to go cold turkey from the shopping for the duration of her process with them, he will still be asked at some point to shop for family needs, with the question being how much Mike will or at least try to sneak those wants into his shopping basket.
- Jennifer calls in Gail to deal with her husband, Bryan, they the parents to two young daughters. Jennifer earns the bulk of the family's money. Bryan's approximate thirty percent contribution - now $20,000 annually as a carpenter - and more goes primarily toward his own vices, namely nights out eating with the boys, copious quantities of good beer, and cigarettes. In addition, he has a thing for nice televisions, he spending most of his time at home in his "man cave" in the converted garage. With the television issue, he now refuses to sleep in his and Jennifer's bedroom since there is no television in the room. Soft spoken Jennifer has given up trying to talk to Bryan about money, as it leads to arguments and Bryan shutting down. As such, neither Bryan or Jennifer, the latter who handles all the household finances, has any idea how deep in debt they are as a family, that debt which is primarily Bryan's in spending on his own vices. Especially as Bryan professes to have his daughters' best interest as his first priority, Gail wants there to be a better balance in the household, meaning Bryan getting out of his holistic adolescent mentality. In a practical sense, it means Bryan taking responsibility for knowing about the household finances, each contributing his or her fair share to the household finances including Bryan taking care of his own debt (with their disposable income his or her own based on what is left over), Bryan making more of an effort to earn more money in his now chosen trade, and Bryan limiting or totally cutting out some vices, namely having a defined amount of beer a week and quitting smoking. But some of the onus is also on Jennifer in standing up for herself which she has been unable to do in their relationship thus far.
- Although Dan is identified as the money moron in his marriage to Lisa, Dan is a willing participant in bringing Gail into their lives as he realizes he has made a mess in the management of their finances which in turn has placed a strain on their marriage, this the second marriage for both. Each party contributes roughly half of their approximately $90,000 annual income. At the beginning of their marriage, Lisa willingly gave up any handling of the finances, which she did in her first marriage, it a responsibility which she hated. Having no credit or debit card, Lisa is given a weekly allowance - her mad money - by Dan. It was the frequency that Dan stated that she could not have any more money on any given week for a larger than usual purchase which twigged in Lisa's brain that something was not right with their financial situation. Lisa had no idea what was happening to their money beyond the visible aspects, such as the building of the back yard swimming pool, the remodeling of the kitchen, and everything associated with their son's hockey, including the socializing of frequent meals out. Dan has not let her into the know even when she has asked. Dan's belief is that his problem has been the inability to say no without having to talk about the financial mess. Beyond the actual money management which includes entertaining themselves with less money, Gail provides them with challenges and supports to be able to communicate more effectively with each other about their finances and life priorities, as well as about planning for their retirement seeing that they are approaching middle age.
- Twenty-seven year old Kyla calls in Gail to deal with her sixty year old mother, Valerie. Kyla knows that this will be an all family process, including her brother/Valerie's twenty year old son, Conor, due to circumstances. Valerie had been retired when the unexpected upended her life seven years ago: her husband asked for a divorce. An entire inheritance was used to pay for Valerie's divorce expenses. Valerie was forced to go back to work into a job in which she earns $60,000 annually. Kyla - who makes $32,000 annually - her partner, and their infant daughter rent the basement in Valerie's house, both to be close to and support Mom, but also to save some money. Conor, who just finished university and has a part-time job earning him $14,000 annually, still lives at home rent-free, with Mom still acting as Mom, largely paying his way. Valerie's primary problem is that she didn't change her spending habits following the divorce despite her changed financial circumstances, keeping things the same in part to maintain an even keel for Kyla and Conor. An added expense is being Grandma, as she spoils her granddaughter. The three of them have never had the money talk, Valerie who feels it's her role to protect her kids, despite they being adults, from those sorts of problems. She, in turn, also doesn't want to be a financial burden on them in her retirement years. Gail finds that all three knew that there was a money problem, but suffered by themselves in silence until now. Gail wants the most fundamental change to happen with Valerie as the role model for her kids. Beyond curbing the spending, Valerie also has to plan for what will hopefully be her imminent retirement with some financial security, that imminence which includes being an empty-nester and downsizing.