Let’s be real for a second. If you grew up in the mid-2000s, you definitely spent at least one Saturday morning wondering if Hannah Montana and Oliver were ever going to actually get together. It felt like the natural Disney Channel trajectory, right? The goofy best friend finally notices the girl next door is a pop star, they have a "will they, won't they" moment, and suddenly they're the school's "it" couple.
But it never happened.
Honestly, that’s one of the weirdest and most refreshing things about the show when you look back on it with adult eyes. In a world of "ships" and forced romances, the bond between Miley Stewart and Oliver Oken stayed strictly platonic—well, after that slightly traumatizing first episode where he was basically a high-level stalker.
The "I Worship at Her Feet" Phase
Remember the pilot? Oliver was obsessed. Like, actually obsessed. He called Hannah Montana a "goddess" and famously told Miley and Lilly that one day he was going to be "Mr. Hannah Montana." He even refused to wash his hand after he thought Hannah kissed it (spoiler: it was actually Lilly’s dog).
It was a classic setup.
When Miley finally revealed her secret to him in the second episode, "Miley Get Your Gum," it wasn't some romantic moonlight moment. She did it to save him from himself. She chewed a massive wad of gum—something Oliver famously hated—and smeared it on his face to prove she wasn't some perfect deity. He fainted. Obviously.
Once the shock wore off, the writers did something brave: they let the crush die.
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Most shows would have dragged out the "Oliver is in love with his best friend's alter ego" plot for three seasons. Instead, the show pivoted. Oliver became the "brother" figure, the one who saw Miley as just Miley—the girl who was bad at sports and occasionally made questionable life choices.
Hannah Montana and Oliver: The Dynamic That Broke the Trope
Why didn't they date? It’s a question that still pops up in fan forums and TikTok retrospectives.
If you look at the 2000s sitcom landscape, the "best friend to lover" trope was the gold standard. But Hannah Montana and Oliver worked because they were fundamentally different people. Oliver was the "Locker Doctor"—chilled out, a bit of a dork, and obsessed with his own hair. Miley was a neurotic, hyper-focused girl living a double life.
They were each other's anchors.
In the episode "Cuffs Will Keep Us Together," they actually get handcuffed together and realize they don't have as much in common as they thought. They realized their friendship was built on Lilly being the glue. It was an honest, if slightly brutal, look at how teen friendships actually work. You have your "group" friends, and then you have your "soulmate" friends.
The Joannie and Lilly Pivot
Everything changed in Season 3.
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If you were watching "What I Don't Like About You" back in the day, you probably remember the collective gasp when it was revealed that Oliver and Lilly—not Miley—were dating. It was the plot twist nobody saw coming, yet it made perfect sense. They shared the same "sidekick" energy.
This move effectively buried any remaining fan theories about Hannah Montana and Oliver.
While Miley was off dating Jake Ryan or Jesse, Oliver and Lilly were building a long-term relationship that actually outlasted most of Miley's romances. They were "Ollie-pop" and "Lilly-pop." It was cringe, sure, but it was solid.
There was even that one episode, "I Honestly Love You (No, Not You)," where Miley misinterprets a sleepy "I love you" from Oliver and thinks he’s confessing his feelings to her. The episode is basically twenty minutes of Miley panicking about how to reject him without ruining the group. The relief she feels when she finds out he was just practicing for Lilly? That says everything you need to know about where their hearts were.
What Really Happened to Mitchel Musso?
We can't talk about Oliver Oken without talking about Mitchel Musso.
By the time the show reached its final season, Hannah Montana Forever, Oliver was mostly gone. He was written off as being "on tour" with his band or off doing music. In reality, Musso was transitioning to other projects like Pair of Kings and his music career.
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However, behind-the-scenes issues eventually clouded his Disney legacy. In 2011, a DUI arrest led to him being written out of his shows. More recently, in 2023, he made headlines again for a public intoxication and theft incident in Texas. It’s a far cry from the goofy kid who used to wear neon hoodies and solve locker jams at Seaview High.
For many fans, this makes the early seasons of Hannah Montana and Oliver feel even more nostalgic. They represent a simpler era of the Disney Channel—one where the biggest problem was whether your best friend would find out you were a pop star.
Lessons from the Oliver-Miley Friendship
So, what can we actually take away from this?
First, not every male-female friendship needs a romantic payoff. The "friend zone" isn't a prison; sometimes it’s just where the best relationships live. Hannah Montana and Oliver proved that you can have a guy best friend who supports your dreams, keeps your secrets, and doesn't try to make it weird.
Second, the show taught us about boundaries. When Oliver’s obsession with Hannah got too intense, Miley didn't indulge it. she shut it down. She valued the friendship enough to be honest, even if it meant breaking his heart a little bit.
How to Navigate Your Own "Oliver" Dynamic
If you're currently in a friendship that feels a bit like Miley and Oliver's, here are a few things to keep in mind:
- Be clear about the secret: If you're hiding something big (maybe not a pop star life, but something real), tell the people who actually have your back.
- Acknowledge the awkwardness: If one person has a crush, talk about it. Don't let it simmer until someone faints at a beach party.
- Respect the "Glue": Understand that your friendship might change if the "Lilly" of your group starts dating the "Oliver." It's not a betrayal; it's just growth.
The legacy of Hannah Montana and Oliver isn't a love story. It's a story about three kids who grew up in the weirdest circumstances imaginable and stayed loyal to each other. Oliver was the first person to know the truth who wasn't family or Lilly, and he guarded that secret like his life depended on it. That’s worth more than a teen romance anyway.
To revisit the classic moments of their friendship, you can stream the entire series of Hannah Montana on Disney+, starting with the pivotal second episode where the "Hannah obsession" officially ends and the real friendship begins.