When Vinnie, a loveable goofball who doesn't quite act his age, becomes the guardian of his 12 year old buttoned up nephew Wendell, the two experience some growing pains adjusting to the new arrangement.
To get a date with Wendell's attractive Vice Principal, Vinnie asks him to pretend to be a problem student. However, Wendell gets more than he bargained for when he's sent to detention and surprisingly makes a new friend.
Wendell wants to take up magic as a hobby against Vinnie's wishes, forcing Vinnie to admit his own embarrassing outing as an amateur magician and teaching him that he won't always be able to protect Wendell from failure.
Vinnie and Wilma's sibling rivalry gets the best of them when they resort to dishonorable tactics to help Wendell sell candy bars for a school fundraiser in order to win a bike.
Hosting a sleepover proves challenging when instead of helping Wendell make new friends, Vinnie takes over and becomes the center of attention. In the end, Wendell proves he also knows a little bit about how to have a party.
When Wendell gets caught up with a snobby group of Magnet school kids, Vinnie struggles to be a better disciplinarian at the urging of his judgmental father.
Wendell and Vinnie try to join a swanky car pool at school, but their test run doesn't go smoothly. Elsewhere, Wilma persuades Taryn to file a lawsuit against a beverage corporation.
Wendell befriends a lonely student from Holland, Jann. But when Jann abandons Wendell for a cooler crowd, Vinnie decides to help Wendell win him back by putting them in a situation where they're forced to spend time together.
Wendell and Vinnie try to locate the mystery owner of a tote bag they found, but Vinnie learns Wendell doesn't respect his intellectual contribution to the team. Vinnie must solve the mystery first to earn Wendell's respect.
To beat out his main competitor for a piece of movie history, Vinnie forces Wendell to lie for him. To get even, Wendell hawks Vinnie's prized possession without realizing its full value, and now must find a way to get it back.
Vinnie takes a road trip with "The Toad," a friend from his past, which takes a very wrong turn. Meanwhile, Wendell stays with Wilma, who makes him realize he may have taken Vinnie's easygoing ways for granted.
Vinnie meets his favorite comic book author, also a single parent, and sets up a playdate for Wendell and the man's aggressive son. However, as the boys become buddies, Vinnie's new bromance loses steam.
Wendell asks Vinnie for help convincing the PTA to build a school garden, and Vinnie soon discovers PTA politics. Vinnie and Wilma learn this was the dream of Wendell and his mom, and go to any lengths to help him fulfill it.
When Vinnie meets a girl who's way out of his intellectual league, he uses Wendell's "smart guy" talking points to impress her. Meanwhile, Wendell has to pretend that everything in Vinnie's man-child apartment belongs to him.
Vinnie brings Wendell to work hoping he'll love it, but instead Wendell changes it into everything Vinnie hates. Wilma takes Taryn's hip-hop class and learns she's a drill sergeant, oddly compelling Wilma to earn her respect.
Wendell becomes head of the dance committee and enlists help to make it the most successful Hines Middle School social event ever. As Vinnie re-connects with a former crush, Taryn sees him in a whole new light
