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She also has a crush on Justin Timberlake and supposedly spread a rumor that he's dating Lola.
In the unaired episode No Sugar, Sugar, it is mentioned that Lilly had a crush on her her french teacher during Year 8 (7th grade).
(Lilly and Matt reconcile at the end of the episode after Miley was found liable for Lilly's suffering in the Teen Court.) Lilly's celebrity crush is Orlando Bloom.
But when Lilly announces that she loves Oliver, Miley tells her the truth.
Miley and Lilly then hatch a plan to get Oliver back only to find out that Oliver was in fact, practicing saying "I love you" so he could say it to Lilly.
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.
Miley also has a dream in which Lilly starts dating Jackson, and must learn to accept her friend for who she is.
This leads to Miley believing that Oliver was in love with her while dating Lilly.
Miley thinks that all she has to do is wait till Lilly moves onto someone else and that Oliver will change his mind.
When Miley wakes up, she believes the dream was real and is pleasantly surprised when Lilly reacts with disgust.
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.
In the end of episode Lilly and Oliver both say that they love each other.