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, but 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.

When Wendell seeks Vinnie's advice about asking a girl to be his valentine, it gives Vinnie an idea about how to approach Taryn.

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.