When Miss Hoover asks her students to research their family history, Lisa is horrified to discover that most of her ancestors were bad people - a motley crew of horse thieves and deadbeats. But while rummaging through the attic, Lisa happens upon a diary kept by her ancestor, Eliza Simpson. As Eliza's story unfolds, Lisa learns that her family was part of the Underground Railroad, a group that helped slaves escape to freedom. Eliza recounts liberating a slave named Virgil, but when Lisa presents her findings at school, some of her classmates refute it, leaving Lisa determined to exonerate her family's name.

Principal Skinner announces that Mrs. Krabappel was called out of town and budget cuts dictate that, until she returns, the school's two fourth grade classes will merge. Bart reluctantly shares a desk with Nikki and develops a flirtatious rapport. Bart talks to Grampa about his new crush, and at Grampa's suggestion, gives Nikki a kiss. But when Nikki starts sending Bart mixed signals, he swears off women forever. Meanwhile, Lisa's classmates ostracize her for being an overachiever, and First Lady Michelle Obama, a self-professed nerd, comes to Lisa's defense.