In Pilot, Kennedy begins her senior year at Mystic Falls High School, a grade above her friends, Bonnie, Caroline, and Elena. After school, Kennedy heads to her job as a library assistant and unknowingly runs into Damon Salvatore, who calls her Eliza. She awkwardly corrects him before he tells her he mistook her for an old friend. During the Back to School Party, Kennedy hangs out with Bonnie and jokingly calls her prediction about the crow an "omen of death". She calls 911 when Vicki gets attacked and later heads to Mainline Coffee with Bonnie and Caroline. When she realizes she's out past her curfew, she hurries home but not before bumping into Damon again, who offers her a ride home. Kennedy declines and gets scolded by her father when she gets back to her house.
During The Night of the Comet, Kennedy bumps into Damon again in the library. The two finally properly introduce themselves to each other, and she helps him find the library's copy of The Vampire Chronicles by Anne Rice. After work, Kennedy meets back up with Caroline, Bonnie, and Elena at the Grill and discuss Elena and Stefan's relationship. Later that day, Kennedy and Bonnie are at Sheila Bennett's, Bonnie's grandmother, house, eating dinner. They listen to Sheila talk about when she and her best friend Evelyn Warren snuck out of town to see the Beatles play in D.C.. The next day, the town is gathered to watch the comet in the Square. While wandering through the crowd, Kennedy gets the oddest sense of deja vu and glances next to her, expecting to see Damon next to her and commenting about constellations, but he is not there. Vicki goes missing, and Kennedy and Bonnie check in the back alley behind the Mystic Grill for her. However, instead of finding Vicki, Kennedy finds the library's copy of The Vampire Chronicles on the ground as if it fell out of someone's jacket or bag. She pockets the book. That night in her bedroom, Kennedy is working on a history paper before she glances at the newspaper her dad had placed on her desk earlier that morning, attached is a sticky note that reads "Reasons to Respect Curfew." The article describes that two more people had been found dead just outside of Mystic Falls. After reading the article, Kennedy looks over to the pamphlet from the comet showing and mutters about it being the harbinger of death, like Bonnie had told the group about Sheila's prediction about the comet earlier.True to her word, Kennedy tries out for the cheer team, despite informing Caroline she doesn't have the time to be on the team. It's at tryouts that she learns Caroline is now dating Damon, who is also Stefan's older brother.
- Damon: "Crazy? Is my blood healing you crazier than you being attacked by—"
- Kennedy: "By a vampire? Than you being a vampire?"
- — Kennedy admits to knowing Damon is a vampire in The Turning Point.