The game allows the player to interact with six heroines in Dear America, including Remember "Mem" from A Journey to the New World, Abigail from The Winter of Red Snow, Hattie from Across the Wide and Lonesome Prairie, Clotee from A Picture of Freedom, Zipporah from Dreams in the Golden Country, and Margaret from Voyage on the Great Titanic. The player uses an instant messaging system and chooses a predetermined question to ask one of the girls. Depending on what questions the player chooses, the girl's story may change.
Players are also able to create their own diary and take personality quizzes.
- Remember Patience Whipple, 1622: "a Pilgrim abroad the Mayflower to the New World."
- Abigail Jane Stewart, 1778: "a shoemaker's daughter nursing Revolutionary War soldiers."
- Hattie Campbell, 1848: "a pioneer toughing it out on the Oregon Frontier."
- Clotee, 1860: "a slave girl seeking freedom from a Virginia plantation."
- Zipporah Feldman, 1905: "a Jewish immigrant aspiring to be an actress in New York."
- Margaret Ann Brady, 1910: "an English orphan preparing for a trip on the Titanic."
- Madame Alexander Dear America Collection, a doll line also based on Dear America.