Irresponsible woman Mackenzie "Mickey" Molng is visiting her sister Poodle, who married into wealth, when Poodle and her husband Christopher are arrested by the FBI for fraud and tax evasion. Poodle asks Mickey to watch her children until things are sorted out. Mickey immediately clashes with oldest daughter Sabrina and neighbor Liz, gives bad advice to middle child Chip, and causes youngest child Ben to have an allergic reaction. Just as Mickey decides she isn't cut out for parenting, Poodle calls to say that she and Christopher are fleeing the country.
Mickey and the kids are forced to downgrade from their temporary residence at a hotel after their financial advisor cuts them off due to excessive spending. Mickey and Sabrina refuse to accept the decision and launder up a plan to prevent anyone from stopping their stride. Meanwhile, Jimmy teaches Chip that the tricks to living in a luxurious hotel can be simple.
Mickey's relationship with Alba is tested when Greenwich divorcee Trish hits rock bottom and becomes the perfect new friend for Mickey. When Mickey sends Jimmy over to help Trish with some home repairs, she begins to question just how casual her relationship with him really is. Meanwhile, Sabrina and Ben take a shot at Chip’s ego.
Mickey and the kids go to great grandmother Rita Pemberton's 100th birthday celebration at her huge mansion. Mickey takes advantage of Rita when she discovers that Rita believes Mickey to be an old friend, but later learns that their friendship was more than just platonic. Meanwhile, the kids' grandmother, Tippy, gives the family an unexpected surprise.
Mickey and Jimmy bring the gang back to their hometown of Warwick to celebrate the retirement of Jimmy’s high school baseball number and discover how much of a big shot he was. When they meet up with old friends, Jimmy learns that Mickey may have had a hand in ruining his chances at a professional baseball career. Meanwhile, Chip and Sabrina find themselves in a pickle with some spoiled Warwick teenagers.
When chaperoning Ben’s school field trip to a trash dump, Mickey and Alba discover that an unfamiliar young boy made his way on the bus back. The two work together to return the lost child but make it extremely difficult for themselves along the way. Meanwhile, Chip and Sabrina take advantage of Colonel’s status as a veteran, only before it comes back to bite them.
Mickey teaches Chip and his friend how to gamble, and they end up losing a large sum of money. In an attempt to win the money back, Mickey uses Sabrina's new relationship with the Junior National Women's Soccer team captain to place a bet on one of their games. Meanwhile, Jimmy becomes overly invested in the soccer team's success.
Following graduation, Mickey and Alba discover that Sabrina is having second thoughts about attending Yale. In their attempt to sway her decision, Alba finds herself heavily involved at a Yale Alumni reunion event. Meanwhile, Chip is keen on re-branding himself before he starts high school, so naturally he decides to throw a party to prove his status.