Chessy is a kind, loving and caring woman. She has been with Nick since Annie and Hallie were born and subsequently has a very close bond with Hallie, perhaps even closer than Nick. She is a very observant woman, quickly noticing the changes in behavior that "Hallie" displays after coming home from summer camp, and (correctly) interpreting that Meredith Blake only wants to marry Nick for his fortune.
Role in the film
Chessy first appears when Annie, posing as Hallie, comes home from summer camp, greeting her exuberantly. She welcomes her into the house and helps her unpack, at the same time telling her about Meredith and voicing her suspicions that Meredith is only after Nick for his money (although she encourages "Hallie" to find that out for herself).
The next morning, Chessy prepares a large breakfast for "Hallie", only to grow concerned when she doesn't seem to be hungry, following that she had very little of the chili she made the day before, Hallie's favorite. Annie reassures her, and she brings up that she was talking on the phone the previous night at midnight in her bathroom (a conversation with Hallie in London). Annie fabricates a story with a clumsiness that Chessy easily sees through, but lets the issue go and tells her that Nick wants to see her after she finishes eating. Chessy's suspicions grow as she only takes a bite of toast before saying she's done. Sammy barks at her, and she has difficulty opening the glass door.
Chessy later confronts Annie after she, thinking she's alone in the room, voices her stress at the situation with Nick and Meredith, without giving specifics. When Chessy reveals herself to have been sitting in a nearby chair, Annie remarks that she "gave her a fright". She then lists the oddities that had been going on since she came home from summer camp, and Annie explains it away by saying that she changed a lot over the summer. Chessy uncertainly accepts the explanation and voices her thought that if she didn't know better, she might have thought she was Annie, though she cuts herself off before saying her name. Correctly interpreting the situation, Annie reveals her identity, and Chessy begins crying in happiness. She keeps her secret from Nick when he comes into the room a moment later and then goes off to prepare something special for Annie. She later looks out of a window following Annie's ballistic reaction to Nick saying he planned to marry Meredith, reaffirming that she knows nothing. (At one point, when Meredith summons her with a bell, Chessy appears, saying "You rang?").
After Annie confirms Chessy's suspicions that Meredith was a gold digger, she contacts Hallie for help, moving up their plans to get their parents back together. While Hallie explains the truth to Elizabeth, Chessy helps Annie set up a rendezvous at the Stafford Hotel in San Francisco, ostensibly for a good location for the wedding, keeping Nick and Meredith ignorant of the truth. Sammy's eagerness at smelling Hallie nearby leads Chessy and Annie away from Nick and Meredith. Chessy loses hold of Sammy as he spots Hallie in an elevator and runs eagerly to her. She then turns away as a drunk Elizabeth talks to Annie, thinking her to be Hallie, and tells her to meet her "upstairs." Chessy escorts Annie to her room and welcomes Elizabeth when she arrives, remembering that she always liked the other woman after she gives her a warm welcome.
Shortly afterward, Chessy meets and becomes infatuated with Elizabeth's butler, Martin, who had also been informed of the full story. They, Annie, and Hallie uncomfortably confide it to Elizabeth before they head down to the pool, observing the reunion between Elizabeth and Nick from a distance. That night, Chessy acts as their server on the arranged date for them, Martin alongside her as a sommelier, and they grow more fond of each other.
When Annie and Hallie coerce Elizabeth into coming home with them for a camping trip before they separate with their respective parents, she manages to trick Meredith into going in her place. She and Chessy look on smugly as the vehicle leaves, the latter remarking that she would pay big money to see Meredith climb a mountain. She and Martin leave for a picnic at around noon and do not return until the following evening, inadvertently spoiling a growing romantic moment between Elizabeth and Nick.
When Nick and Elizabeth reconcile and remarry, Chessy is seen on the ship, and Martin proposes to her. She is last seen in the closing credits photos dancing with Annie and Hallie and having fun with Martin.
- In the scene where Meredith calls Chessy with a bell, her response is “You rang?” This is similar to the Addams Family's butler, Lurch, who says the phrase in response whenever anyone calls for him by pulling a bell cord shaped like a hangman’s noose, which makes a gong-like sound.