Lilly Truscott

 Lillian "Lilly" Truscott (portrayed by Emily Osmet) is the best friend of Miley Stewart and girlfriend to Oliver Oken. Under the alter ego Lola Luftnagle, 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 is considered a tomboy in the beginning of the series but developed a "girly girl" side as the show progressed.

Personality
Lilly is a huge fan of Hannah Montana before she learns that Miley is Hannah. She is extroverted, excitable, clumsy, and impulsive. She is also very athletic, and her hobbies include skateboarding, hockey, cheerleading and surfing. She is thought of as a tomboy. Lilly does cartwheels whenever she is excited about something such as getting asked to be someone's girlfriend (My Best Friend's Boyfriend) and getting to go to Washington D.C. (Would I Lie To You, Lilly?). In Joannie B. Goode, she says she takes piano lessons on Wednesdays, but has never been seen playing

Lilly and Miley have a close friendship (Milly Friendship) that can sometimes be thought of as romantic (Milly Relationship). Although they often have disagreements and huge fights, 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.

Lilly is tone deaf, as discovered in the episode Song Sung Bad. Miley (without telling Lilly) remixes her rendition of One In A Million to make her voice sound like Hannah Montana's. 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 a 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 later. However, some of the things Lilly says when impersonating Miley (such as "possum") can rub off on Miley and make her develope the habit for a short while of saying some of these things.

Despite being somewhat of a tomboy, Lilly is very concerned about her appearance and what people think of her. She insists not to enter a skating competition after her dog eats her contact lenses and does not want to be seen with her horn-rimmed glasses. This episode, besides showing viewers that Lilly does have some girly nature, tells that Lilly has bad eyesight and is virtually blind without glasses or contacts. She is occasionally more excited about wearing cute outfits than of solving problems. Since Season 3, Lilly has been dating Oliver Oken, and at the end of the series they are still together, keeping up a long-distance relationship (Liliver).

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. This shows that she had grown fashionably as a character and her fashion sense has changed.

In You Gotta Lose That Job, Lilly mentions that she would like to be teacher and that she would be supportive, fun she would not allow her students to talk back. She has an 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. However, this crush seems to have been diminished.

As Lola Luftnagle
In order to help Miley keep her secret, Lilly attends all Hannah Montana events wearing a disguise and posing as Hannah's companion and assistant Lola Luftnagle. In the episode Miley Get Your Gum, Lilly originally called her alter ego Lola LaFonda, but she later settled for the surname Luftnagle in It's My Party and I'll Lie If I Want To. Since then, Lilly has continued calling her character Luftnagle. Lilly claims that Lola is "the daughter of oil baron Rudolph Luftnagle, sister of socialites Bunny and Kiki Luftnagle."

Lola wears very tight clothes that have loud colors. Emily Osment once said in a backstage interview that Lola has some very tight pants that she is unable to sit in. Lola also enjoys jewellery and is often found in rings, necklaces, huge earrings and bangles. Lola usually has short, brightly colored wigs; however, in Season 3 the wig is a little bit longer than the wigs used in the previous seasons. In almost all episodes Lola wears a differently colored wig, from white to red to purple to pink to blue and her enemy is Traci Van Horne. There are about 80 wigs for Lola due to all of her different hair colors and she is apparently dating Justin Timberlake, according to an internet rumour she has "no idea" who started.

Boyfriends and Crushes
Lilly goes through a few short dating relationships throughout the show, going through only one long-term serious one. She has a crush on actor Jake Ryan and, at a 70's dance, the two go on a date until Miley jealously breaks them up. She also had an episode with her classmate Lucas until Miley discovers he is a cheater and breaks them up.

Miley once has a dream in which Lilly starts dating her brother Jackson. Miley must learn to accept her friend for who she is. When Miley wakes up, she believes the dream was real and is surprised but yet gleeful when Lilly reacts with disgust when Miley asks her if she likes Jackson.

In You Are So Sue-Able to Me, Lilly has a crush on fellow classmate Matt Marshall, who returns her feelings. However, on the show it is never revealed if they actually dated or not, as Miley messed their relationship up. Although they patched up again soon afterwards, it is most likely that the two split up before Get Down, Study-udy-udy took place. Lilly's celebrity crush is Orlando Bloom, who has been mentioned as Lilly's crush several times, especially in Season 1. 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 isdiscovered that Lilly once had a crush on her French teacher during 7th grade. She wore a beret to school and said "Oui, Oui" so many times that some people began calling her "Tinkles Truscott".

Lilly longest, most passionate relationship when she started dating Oliver Oken in season 3 of the series. Their friendship started in preschool when Lilly held his hand. Lilly stated that the only reason she did this was because she wanted to borrow his crayons as they were the 64-Pack which came with the sharpener. For several years the two were best friends but in What I Don't Like About You, they begin dating. They try to keep this a secret from Miley and fail at doing this, as Miley finds them kissing. However, after a argument over their favorite bands the two broke up. Miley made an extremely short Indiana Joannie movie and they made up and decided to continue with their relationship. In Promma Mia, the two danced together and in He Could Be the One, Lilly says she loves Oliver. Their nicknames for one another are Ollie-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 developes when Miley, who is sleeping in a hospital room due to a broken ankle), overhears Oliver say "I love you" to her sleeping body. When it was actually said as practice for Lilly, hearing 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 declares that she wants to tell Oliver she loves him, Miley is forced to tell her what Oliver said. In the end the two find out why Oliver told Miley he loves her and Lilly and Oliver yet again recoincle. 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, making Lilly super upset. Because of this, the two break up. They make up again after Rico helps them get back together by writing a fake poem and send it to Lilly but signed it as "Oliver Oken." Rico says he was only doing it so his business wouldn't fail, as Oliver's bad mood after Lilly dumps him was driving his customers away.

In the episode Judge Me Tender, Oliver’s singing career takes off, but all the attention he receives causes him to forget all about Lilly. As a result, Lilly asks Miley as Hannah, who is the celebrity judge for that season as a replacement, to kick him off the show which results in them breaking up. Miley, however, lets Oliver succeed to the semi-finals of the show. Afterwards, Miley manages to confront Oliver and tell him what a jerk he's being, which results in his making up with Lilly.