Cindy Smith is a native of Winfield, Kansas and a childhood friend of Mary Ann Summers. The two of them were such good friends that they developed a secret handshake between them, and they re-bonded years later after Mary Ann turned up alive after being believed lost on the S.S. Minnow in the South Pacific. She eventually got to meet the Skipper and Gilligan, who knocked over the bridal tower, two rows of chairs and the bridal chamber at Mary Ann's wedding. During the years Cindy believed Mary Ann was dead, she became romantically involved with Herbert Rucker, Mary Ann's old boyfriend, eventually marrying him at Mary Ann supposed wedding to Herbert.
- Cindy Smith was played by actress Barbara Mallory.