Chessamay "Chessy" Chestnut is Maybe's mother. Chessy is a blonde bombshell with big hair, big boobs, and a big personality. She charms the pants off men and is working on getting married for the seventh time. in addition to being a serial marryer. Chessy is also an alcoholic. Whenever something doesn't go right, Chessy turns to the bottle to resolve her problems.
Chessy runs a charm school, where she also consults with beauty pageant contestants to help them win their own crowns. In her younger days, Chessy was a beauty pageant contestant and winner—making it all the way to the Miss America Pageant. Chessy didn't make it to the Miss America contest because she was afaraid to get on the plane to leave Kissimmee.
