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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.
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.
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.
When Miley wakes up, she believes the dream was real and is pleasantly surprised when Lilly reacts with disgust.Lilly Truscott (born July 14, 1992) played by Emily Osment, is one of the main characters of the show and is the off again/on again friends with Miley and best friends of Oliver. Lillian Emmaline Truscott is the best friend of Miley and Oliver and has been a huge fan of Hannah Montana since before she knew that Miley was Hannah Montana. In the episode Mascot Love she tried out for the cheerleading team and made it, but it was never mentioned again. Lilly and Miley argued because Lilly held Oliver's hand in pre-school so she could have his 64 pack of crayons with the sharpener, which Lilly says wasn't a crush but Miley says it was.Lilly was the first to find out Miley's secret when she snuck into Hannah's dressing room after a concert. Lilly did admit to having a crush on Jake Ryan but when she saw that he liked Miley, she encouraged Miley to pursue him.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.