Despite being weary of Ravi's seven-foot Asian Water Monitor Lizard, Mr. Kipling, Jessie comes to the lizard's rescue after the head of the condo board attempts to ban Mr. Kipling from the building. Meanwhile, Zuri brings home an another imaginary friend, and Luke and Emma compete against each other in a school photography class.

Jessie and Zuri were making a video to send to Jessie's old friend, so Zuri took Christina Ross's tiara so Jessie can wear it. Jessie accidentally knocks the tiara off her head and over the ledge, where it lands in Mrs. Chesterfield's hot tub. When Mrs. Chesterfield refuses to return the tiara, Jessie and Zuri convince Bertram to ask Mrs. Chesterfield on a date so they can take it from her apartment. Meanwhile, Ravi, Emma and Luke all see a video online and have an idea to make Mr. Kipling a star. The title is a send-up of the film title Romancing the Stone.

Jessie is tasked with ungluing Mrs. Chesterfield's hands from her head, while Ravi attempts to uncover who switched Mrs. Chesterfield's hair gel with stay stick glue. Meanwhile, Tony and Jessie plan a fun date.

Ravi is having trouble finding a home for all 12 of Mr. Kipling's baby lizards.

Jessie and the kids are excluded from the building Halloween party. They throw their own party, which is interrupted when Emma and Luke become possessed by evil spirits.

Jessie hits it off with a new guy she meets in the park named Brooks, unaware that he is Ms. Chesterfield's son.

Unhappy with her son's budding relationship, Mrs. Chesterfield hires Bertram; she's hoping he finds dirt that will cause Brooks to break up with Jessie.

Jessie and the Ross kids plan a tropical Christmas at the family's Hawaiian villa where Jessie reunites with old friend and superstar, Shayelee Michaels.

The Ross family faces an unexpected dilemma when they find out their parents have lost all their money and must learn to live without it.

Bertram has had enough, so decides to quit and to go work for Mrs. Chesterfield. Meanwhile, the Ross family hires a new butler, Roger, who takes his job very seriously.

Jessie has to relearn all the "special skills" she listed on her resume for a commercial that she booked. Meanwhile, Ravi convinces Luke that a meteor is headed towards Earth.