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.

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 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.

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.

When Alba leaves to go on vacation, Mickey appoints Sabrina to babysit Ben when she and Jimmy leave for a night out. When Sabrina decides that a night out with her friends is much more appealing, she and Mickey get into an argument and end up in jail. Meanwhile, Jimmy meets a new friend.

When Mickey and Alba catch Ben lying and try to teach him a lesson, naturally their plan backfires. Meanwhile, Chip devises a spiteful plan to be crowned "Prince" at his school formal, and Jimmy teaches Sabrina how to dance.