Mickey's poor parenting skills are only made worse when a popular kid in Chip's class comes to the house for a sleepover. Meanwhile, Mickey and Alba try to tame Ben's fear of monsters.

Life in the Pemberton mansion gets even more chaotic when the kids catch a pair of intruders trying to break in. Then, Mickey tries to protect the kids in a case of mistaken identity.

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. Meanwhile, the kids' grandmother, Tippy, gives the family an unexpected surprise.

Sabrina tells Mickey she wants to augment her figure, so Mickey decides the best way to dissuade her from doing so is to do a test-run in public. Meanwhile, Jimmy takes Chip and Ben to a baseball game to teach them how to be more masculine.

Mickey takes Sabrina to visit her mother in jail to gain closure, but it turns out Mickey may be the one who needs it the most. While visiting his father, Chip learns that he is in danger behind bars and enlists Jimmy for help. Meanwhile, Ben inadvertently distracts the bullies.

When Mickey's attempts at disciplining the kids are ignored, she decides to shed her "cool aunt" persona and lay down the law.

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.

Mickey tricks Sabrina into thinking she's pregnant to scare her into taking birth control. Meanwhile, Chip considers a vasectomy to thwart gold-diggers, but has not even kissed a girl.

After Chip gets roped into a scandal, Sabrina leads a School Honor Board trial against him, where he must choose between snitching on his teammates or taking the fall. Meanwhile, Alba dents the family Bugatti, with Ben as a witness.

The Pemberton kids learn some lessons in "tough love," when Mickey calls in their overly strict grandmother to discipline them. Meanwhile, Mickey reunites with Jimmy.

When Mickey learns they've all forgotten Ben's seventh birthday, the family is forced to put their selfish tendencies aside for one day and throw him the celebration he deserves, which proves way harder than it sounds.

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 Mickey finds out Ben takes medication to keep him focused, she is determined to prove that he is a perfectly functioning kid without it. She and Alba take over his struggling science fair project, but become overly invested, while Jimmy helps Chip make his secret boys club cool again.

While Mickey and the gang visit New York City, they learn that Jimmy has become quite successful at an investment firm.

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.

Sabrina decides to throw a get-together with talented artists in order to impress them. After learning that Ben's new friend has a celebrity mom who loves art, Mickey decides to co-host the event in order to sway her. Meanwhile, Chip goes on a spontaneous camping trip with Howard.

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'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.

Sabrina believes she's a shoe-in at Yale, but on the day of her interview, she takes a risk that may ruin her chances and jeopardize her future. Meanwhile, Alba gets a visit from her cousin and must pretend to be a maid again, so her family doesn't disown her.

Mickey tries to quit smoking. Meanwhile, Ben meets a new friend.

Sabrina's relationship with her poetry teacher has Mickey concerned, so Mickey takes matters into her own hands and humiliates the both of them in front of her peers. Meanwhile, Chip enlists Jimmy's help to improve his ranking on the 8th grade hot list.

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.