Lilly loves skateboarding and is seen skateboarding into the Stewart's house numerous times. In the first season, Lilly is much more of a tomboy but in the second season, Lilly becomes more girly.
In "You Are So Sue-able to Me," Lilly has a crush on her schoolmate Matt Marshall, but it is never revealed if they actually dated.
After Matt asks Lilly to a dance, Miley tries to get Lilly to change her tomboy image so that Matt will find her more attractive.
Lilly often accompanies Hannah to her events using the alias Lola Luftnagle.
In Miley Get Your Gum, Lilly called herself Lola Lu Fonda but has been known as Lola Luftnagle ever since.
Lilly starts her most significant relationship when she started dating Oliver Oken in season 3 of the series.
Their friendship started in preschool when Lilly held his hand in order to share his crayons. Lilly experiences a few short-lived dating relationships.She dates actor Jake Ryan (Cody Linley) at a 70s dance until Miley jealously breaks them up, and her schoolmate Lucas (Sterling Knight) until Miley discovers he is a cheater.In I Honestly Love You (No Not You) a love triangle appears when Miley (while alseep in the hospital because of a broken ankle), overhears Oliver say "I love you" while talking to Miley.This leads to Miley believing that Oliver was in love with her while dating Lilly.Joannie and Lilly were enemies since second grade when Joannie cut the string on Lilly's kite and popped Lilly's balloon.