Jessie agrees to accompany Bertram to his high school reunion, so Bertram can show an old classmate Eric Booth how successful he is. Jessie helps him make up an elaborate backstory about his life and pretends to be his girlfriend.
Jessie is back for a third season and is busier than ever! She takes on an acting agent, becomes an understudy to a famous actress, all whilst continuing to manage the chaos of being nanny to Emma, Ravi, Luke and Zuri. Jessie is learning to manage conflict, chaos, her job as a nanny, a budding acting career and her personal life as she attempts to fulfil her dreams and to achieve her ambitions in the big city.