After Jessie accidentally drops a diamond tiara belonging to Mrs. Ross onto Mrs. Chesterfield's terrace, Jessie and the kids must think of a creative way to retrieve it when she refuses to give it back. Deciding their best option is Bertram, they convince him to ask Mrs. Chesterfield on a date so that they can recover the tiara before Mrs. Ross notices it's missing.

Jessie is shunned by New York City's most intimidating nanny. Meanwhile, Bertram teaches Ravi and Luke how to wrestle.