Jessie: Season 1, Episode 12

1 - 12: Romancing the Crone

Jessie and the kids must think of a way to get back Mrs. Ross' tiara from Mrs. Chesterfield's terrace after Jessie accidentally drops it there. They decide Bertram is their best option and they make him ask Mrs. Chesterfield out on a date so they can retrieve it before Mrs. Ross asks for it back.