Jessie decides to write Tony a song for their first anniversary. However, when she thinks Tony forgot their special day, she ends up writing an angry song that ends up going viral on Emma's vlog. Meanwhile, Ravi is miserable over his many gym class failures, so Luke decides to help him build his self-esteem by letting Ravi finally win at something.

When Jessie discovers Zuri is a chess prodigy, she encourages her to compete in a renowned chess competition. Meanwhile, Luke and Emma suspect Bertram was a jewel thief before becoming a butler.