Chessy is a kind loving caring woman. She is unaware of Annie's presence but is aware of it when she notices that "Hallie" has different mannerisms and a change in appetite. Once it's revealed that she is really Annie, Chessy then decides to go along with the twins' plot to reunite Nick and Elizabeth. She shows a dislike for Meredith Blake, this is shown when she calls Sammy a good dog after he snaps at her.
Chessy becomes infatuated with Martin, Elizabeth's butler, and teams up with him to reunite her and Nick. After Elizabeth agrees to go back to Nick's house, she and Martin start to bond.
When Nick and Elizabeth reconcile Chessy is seen on the wedding ship, and is proposed to by Martin. She is last seen in the post credit photos dancing with the twins and having fun with Martin.