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Lilly does cartwheels and backflips whenever she is excited about something such as getting asked to be someone's girlfriend in "My Best Friend's Boyfriend" and getting to go to Washington D. Episodes which significantly deal with their relationship include "Lilly, Do You Want to Know a Secret? ," "You're So Vain, You Probably Think This Zit is About You," and "Cuffs Will Keep Us Together." In Season 3, Lilly moves in with Miley after her mom moves to Atlanta for a job.
(She is virtually blind without her glasses.) Sometimes she is more excited about wearing cute outfits than of solving problems.
She is currently in the series dating Oliver Lilly is seen in the first season as a tomboy and wears a lot of hats but not so much during Season 2 and 3.
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 the episode "More Than A Zombie To Me", while at the beach, it is shown that she is wearing a bikini under her cover-up.
In 'You Gotta Lose That Job', Lilly mentions that she would like to be teacher and that she would be supportive, fun but no talking back (that is unacceptable, Lilly says).
Miley (without telling Lilly) remixes her rendition of "One in a Million" to make her voice sound on key.
Lilly, believing that she is a great singer, challenges classmate Amber Adison to a singing competition in front of their whole class.
Lilly proudly declares to be singing "I Got Nerve" to which Robby replies, "You sure do." Despite being somewhat of a tomboy, Lilly is also seen to be very concerned about her appearance.