Oliver and Lilly started dating in the third season, and dated to the end of the series. They are uncommonly referred to as "Lolliver".
Promma Mia: This is the fourteenth episode of Season 3. It centers around Miley's promise to Aaron, a seemingly geeky guy at their school, and a last-minute phone call with David Archuleta (who guest stars as himself), asking her to sing a duet with him. Miley is torn between having to do the right thing and doing something only for herself. Although Lilly and Oliver are not part of neither the plot nor subplot, they have some moments in the beginning of the episode and their prom picture taken towards the end.
In the beginning of the episode, Oliver and Lilly are seen linking arms and walking down a flight of stairs at school. They stop at a group of girls and Oliver says, "Oh, I'm sorry ladies. It's too late, but don't hate, Olly's already got a prom date!" and winking at them while pointing to Lilly at the words "prom date". Lilly points at herself before waving to the girls and mouthing the words "I'm sorry," to them. They turn a corner to meet a couple of boys and Lilly says, "Oh, hey, Zack. You can have your eggs, and you can have your bacon, but you can't have Lilly, 'cause she's taken!" She motions to Oliver at the word "taken" and Oliver proudly says, "Yeah! Yeah! Oh, did you see that? Did you see that?" while pointing to Lilly. Lilly coolly says, "See ya," to the boys before she walks away. Funnily enough, the group of girls and the pair of guys seem unaffected by them.
He then turns to her, telling her that she "is just so adorable", which Lilly immediately responds with, "No, you are!" He then says, "Let's go to prom together," and she says, "Okay!" Lilly then talks about how "it's so great not having to sit around and praying that the one guy you really wanna go with will ask you, that feeling of being so desperate, so needy, so..," then momentarily stops to stare at Miley who is staring at "Hottie LaMottie" and willing him to ask her before pointing at Miley and ending her sentence with "..so that." Oliver then puts his arm around Lilly and asks her if that's what she used on him (to get him to ask her out) and Lilly plays along, saying "Yeah, you bet," before making a weird face and walking to sit next to Miley.
After Miley tries, and fails, to get Hottie Lamotty With the Swimmer's Body's attention, Oliver and Lilly sit on either side of her. While Oliver's sitting down, he dramatically sighs, "Single people," to which Lilly adds on with, "So sad," while stroking Miley's hair. Oliver then says that she is "so cute" and Lilly responds that he's also "so cute" before Oliver says that she's cuter, to which Lilly thanks him for, and Oliver goes on to tell her that she's the cutest girl he's ever seen. As they have a "love fight", they rise from their seats and are staring adoringly at each other as their faces come closer. Miley seems to have gotten enough of the two and places a hand over each of their faces, pushing them back down.
The next scene, Miley is seen checking herself in a handheld mirror in front of her locker. Lilly whisper-yells, "Hottie at three o'clock!" Miley throws her mirror into her locker, slams it shut, flips her hair, and poses with her hand behind her neck and another hand on her waist while smiling broadly. Oliver walks into the scene and slides his arm around Lilly's shoulders, both of them smiling. Miley scrunches her face up and disgustedly says, "Ew! I wasted a good hair flip on Oliver?" while straightening up. Oliver drops his arm from Lilly's shoulders and Lilly says defensively, "What? He's a hottie to me," again triggering Oliver's "You're-So-Cute" comments and yet another "love fight". Miley stops them by saying, "Okay, never not gross." Oliver puts a hand next to his mouth and sings in a high-pitched voice, "Bitter," to Lilly, and Lilly nods in agreement. Oliver walks away and isn't seen until their prom pictures get taken.hggfffgggggfgf
What I Don't Like About You: Miley asks what Lilly and Oliver danced to and said it would be 'their song'. They argued whether it was Radiohead or Coldplay and then argued over which was better. Miley told them to move on from the subject and asked them where their first date was. Oliver said that they went to the movies but Lilly replied angrily and said that they went ice-skating. Olilver then called her 'that one' so they got mad and walked away from each other. Miley managed to get them back together by making them watch an edited short-film she made and played the parts of both of them called "Indiana Joannie and The Curse of The Super Annoying Friends". It gets them back together.
I Honestly Love You (No, Not You): Lilly and Oliver try to get ready to tell each other that they truly love each other. Miley, Lilly and Oliver went on a Ski Trip but Miley fell and had to go to the hospital where she was out cold. While she was out cold, she could hear and see what was going on around her 'like that Kate Hudson movie'. She saw Oliver pacing around the hospital room after Lilly left trying to say something. When he finally said it, it was 'I love you'. Miley kept saying that he can't love her because he should love Lilly but she wasn't heard. Oliver was actually practicing saying it to Lilly. When Miley got better and was sitting with Lilly, Lilly told her she was going to get together with Oliver and Miley mistook this and thought that she was going to break up with him. When Lilly, said she was going to tell him that she loved him, Miley was shocked. She told Lilly that she heard him say he didn't love her, and Lilly started endlessly crying. Lilly was even more upset when she found out that Oliver was in love with Miley, but Miley reassured her that she didn't feel the same way. Miley told Lilly that if she took a picture of her with another boy and showed it to Oliver he would realise how big a mistake he made. Miley tried to make Lilly kiss a boy named Gill, and she paid him to do so. Oliver was shocked when he saw Lilly 'inches away from kissing another guy'. Lilly explained how she was told he loved Miley, but Oliver explained that he was actually practicing to say 'I love you' to her.
B-B-B-Bad to the Chrome: It's Lilly and Oliver's 100 day anniversary, Lilly gives Oliver a gift but is then shocked that he forgot their 'special day'. They have a brief break-up, which makes Oliver very depressed and stressed-out and this affects his career at Rico's Surf Shop, leading him to quitting. Oliver helped Rico's business and income so losing him had a negative impact on his gains. So, in order to get Oliver back and into his 'Mr. Happy' mood, Rico writes a love poem for Lilly and signs it as Oliver, which reunites the two and gets Oliver working at Rico's Surf Shop again.
No Sugar, Sugar* : Miley and Lilly mistakenly believe that Oliver has a crush on the school nurse when they see him giving her candy. When they instead learn that Oliver is secretly dealing with the news of being diabetic, the friends work overtime to keep him away from all things sweet. This is not exactly to be classified as a 'relationship bump'. *Note: This episode was not aired.
Judge Me Tender : Oliver auditions for the reality show "America's Top Talent" while Hannah is a judge. His performance is outstanding and he becomes an overnight hit but the attention that he receives from other girls causes him to neglect Lilly. Lilly asks Miley to give him a bad review after his next performance so that he won't progress to the next round. Unfortunately for Lilly and Miley his performance is so good that Miley is torn between her loyalty to Lilly and honesty in appraising Oliver's performance. Lilly gives Miley permission to give Oliver a good review. After the show, Miley talks to Oliver and he apologizes to Lilly.
- Miley: What about Lilly? You guys would be perfect together!
- Lilly: Excuse me?
- Miley: You're both stubborn.
- Lilly and Oliver: [in unison] I am not!
- Miley: See, you always agree with each other!
- Lilly and Oliver: No, we don't!
- Miley: I am definitely seeing a couple here!
- Lilly and Oliver: You're not, because I'm not! Whew!
- Miley: Ugh! I go now!
- Lilly and Oliver: How?
- Miley: Because, I hate you both and i gonna kill you!
- Lilly: In case things between you and Hannah didn't turn out, just remember, you're still Smokin' Oken
- (Miley Get Your Gum)
Miley: [talking about Oliver] ...The first girl to like him since pre-school.
Lilly: I didn't like him like him. I only held his hand cos' I wanted to use his crayons. He had the sixty-four pack, with the sharpener! (Oops! I Meddled Again)