Lillian "Lilly" Truscott (Emily Osment) is the best friend of Miley Stewart and girlfriend to Oliver Oken on seasons 3 and 4. When Miley is Hannah, Lilly is under the alias Lola Luftnagle, and also "Lola LaFonda." She is also close friends with Hannah Montana and part of her entourage. Lilly/Lola has a huge crush on Orlando Bloom in the episode "The Test Of My Love", and tells Miley that she will see "the Lilly Bloom" when Orlando finally meets her. She also plays a central role in the film Hannah Montana: The Movie.
The character was originally named Lilly Romero and then changed to Lilly Truscott. Miley Cyrus first auditioned for the role but was cast as the main character instead. Emily Osment auditioned for the role after Cyrus was cast.
Lilly was born in and grew up in California and was childhood friends with Oliver. She met Oliver in kindergarten and has been best friends with him ever since. In Judge Me Tender, she describes him as a dead beat when she first met him. She recently lived with her mother Heather Truscott (Heather Locklear) in Malibu. Heather appears in one episode, "Lilly's Mom Has Got It Goin' On," where she briefly dates Miley's father Robby. Lilly's parents are divorced, and her father is an accountant. In season one Lilly claims to have a brother but this is contradicted by her in season three. In "Miley Get Your Gum," Lilly refers to her brother's pet hamster. However, in the episode "Cheat it" Lilly says "Sometimes I wish I had a brother, then I come over here. All better!" In the season 3 episode "The Wheel Near My Bed (Keeps on Turnin')," she moves in with the Stewarts' when her mother gets a job in Atlanta. But after she hears that Miley does not like her staying with them, she goes to stay at her dad Kenneth's (Jon Cryer) apartment only to find it even worse than the Stewart's house. Once Lilly and Miley make up, Lilly goes back to staying at the Stewart's house.
Lilly and Miley have been best friends since about the 6th grade. She discovers Miley's secret in the pilot episode, "Lilly, Do You Want to Know a Secret?" when she sneaks into Hannah's dressing room after a concert and she sees the lucky bracelet that she had given Miley earlier in the episode. Although Lilly is dating Oliver, she looks at other guys. In "Once, Twice, Three Times Afraidy", she gazed at Tim, an old friend from camp, causing Oliver to point to the menu on the side, showing his muscles. Also in "He Could Be The One", she gave advice to Miley stating "whatever choice you make, it's gonna be okay... let's face it, they're both gorgeous!", making Oliver mad. Other than that, she stays faithful to him.
Lilly is a huge fan of Hannah Montana even before she learns Miley's secret. She is extremely extroverted, excitable, clumsy, and impulsive and sporty. She is also very athletic, and loves skateboarding, surfing, hockey, and cheerleading. Lilly does cartwheels 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.C. in "Would I Lie To You, Lilly?". In "Joannie B. Goode", she says she takes piano lessons on Wednesday.
Lilly and Miley have an especially close friendship. Although they often have fights and disagreements, they always manage to restore their friendship, making it all the more stronger. Episodes which significantly deal with their relationship include "Lilly, Do You Want to Know a Secret?," "Would I Lie To You, Lilly?," "You're So Vain, You Probably Think This Zit is About You," and "Cuffs Will Keep Us Together." Although Miley makes mistakes from time to time she always finds a way to help her.
Lilly is tone deaf as heard in the episode "Song Sung Bad." So Miley Stewart (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 Addison 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.". Lilly is also not very good at doing an impression of Miley as shown in the episodes "You Gotta Not Fight for Your Right to Party" and "Miley Hurt the Feelings of the Radio Star", Lilly does an unconvincing and very poor impression of Miley, while pretending to be her when Robbie tries to have a talk with Miley (who snuck out of the house with Jackson after being grounded) in the former, and while substituting for Miley when she is late coming to do her radio show with Oliver in the latter.
Despite being somewhat of a tomboy, Lilly is also seen to be very concerned about her appearance. She refuses to enter a skating competition after her dog eats her contacts and does not want to be seen with her horn-rimmed glasses. (She is virtually blind without her glasses.) Sometimes she is more excited about wearing cute outfits than of solving problems. She is dating Oliver in the series.
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. In Season 2, Lilly starts wearing wristbands in all colors and also in Season 3. In Season 3, Lilly is seen in a lot of episodes to be wearing a gold heart necklace.
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). She has an ongoing crush on Orlando Bloom regardless of her many crushes and boyfriends. She says that any movie scenes where he is shirtless is where she runs the movie in slow-motion.
Lilly is also gothic and a fan of Hot Topic, Dracula, Black Sabbath, Alice Cooper, and Kiss.
Lilly experiences a few short-lived dating relationships and only one serious one. She dates actor Jake Ryan (Cody Linley) at a 70s dance until Miley's 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. 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. 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. However, Matt gets turned off by Lilly's new look and stands her up. However, 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. Bloom is a recurring off-screen character in the show whom Lilly sometimes harasses at parties as Lola. She also has a crush on Justin Timberlake and supposedly spread a rumor that he's dating Lola.
In the season 3 episode "Uptight (Oliver's Alright)", it is mentioned that Lilly had a crush on her French teacher during 7th grade. She wore a beret to school and said "Oui, Oui" so much that people started calling her "Tinkles Truscott".
Lilly starts her most significant and successful 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. Said Lilly, "He had the 64-Pack with the sharpener!" For years the two were best friends, but after a beach party, they decide to date each other (while Miley was away shooting her feature film Indiana Joannie) and we (and Miley) find out in "What I Don't Like About You." However, after an argument over their favorite bands, (Radiohead and Coldplay) they broke up. Miley made a mini-Indiana Joannie movie and they made up and resumed dating. They attended prom together in Promma Mia. In "He Could Be The One," Lilly says she loves Oliver. Their names for each other are "Olly-pop" and "Lilly-pop." In "I Honestly Love You (No Not You)" Lilly tells Miley that Oliver calls her "Lilly-pop" because she had a pimple.
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. Miley thinks that all she has to do is wait till Lilly moves onto someone else and that Oliver will change his mind. 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. In the end of the episode, Lilly and Oliver both say that they love each other.
However, in "He Could Be The One," Lilly tells Oliver that while Lilly may be dating Oliver, Lola is dating Justin Timberlake according to an online rumor "she doesn't know who started."
In "B-B-B-Bad To The Chrome," Lilly and Oliver celebrated their 100th day relationship anniversary which Oliver forgets at first and Lilly was upset. They make-up again after Rico helped them get back together by writing a fake poem and send it to Lilly but signed as "Oliver Oken."
In the episode "Judge Me Tender", Oliver’s singing career takes off, but all the attention he receives causes him to neglect Lilly. As a result, Lilly asks Miley to boot him off the show which results in them breaking up. However, Miley lets Oliver succeed to the semi-finals. Afterward, Miley manages to talk some sense into Oliver, causing him to make up with Lilly.