If you spent any time on the Disney Channel during the late 2000s, you remember Cody Linley. He was the golden boy—Jake Ryan on Hannah Montana—the guy every girl wanted to date. Around 2008, he actually did date one of the biggest rising stars in the world: Demi Lovato.
It sounds like a teen idol fever dream.
But honestly, their "romance" wasn't some polished, Hollywood red-carpet affair. It was messy. It involved a broken-down car, a Jack in the Box parking lot, and some very random grocery shopping. While they were only linked for a short window between 2007 and 2008, the story of their "disaster date" has become a piece of Disney lore that people still bring up nearly two decades later.
The Date That Went Horribly Wrong
Most people think celebrity dates are all private jets and five-star rooftops. For Cody Linley and Demi Lovato, it was more like a scene from a bad sitcom. Cody actually broke down the whole night in an interview with Seventeen back when it happened.
He was supposed to pick Demi up at 7:00 PM. He didn't get there until 9:00 PM.
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Why? Because his car died in the middle of Hollywood after an audition. Imagine being 18 years old, trying to impress the girl who just starred in Camp Rock, and you're stuck in a Jack in the Box parking lot with your hood up while a stranger talks to himself nearby. Cody was literally back there with a toolkit trying to revive his car just so he wouldn't blow the date.
Demi to the Rescue
When he finally made it to her place, things didn't exactly smooth out. As they were driving to dinner, the car started making "crazy noises" again.
Most stars would have called an Uber (well, a limo back then). Demi didn't.
Cody says she was actually incredibly sweet about it. She got out of the car, held the light for him while he tinkered with the engine, and even gave him repair advice. Apparently, she was a bit of a "tech geek" and helped him adjust his phone settings to make the flashlight brighter so he could see what he was doing.
They eventually made it to a steakhouse. Because they were so late, Demi’s parents actually let her stay out until 11:00 PM, which was a big deal considering she had a 5:00 AM flight the next morning for work.
Why Cody Linley and Demi Lovato Didn't Last
After dinner, the night got even weirder. They went to a grocery store.
They didn't buy anything romantic. They bought toothpaste and tweezers.
Cody eventually got her home safely, but then he got lost on his way back to his own house. It was a chaotic, "up and down" night that he later described as his most disastrous but fun date ever.
But that was pretty much it.
The two remained friends, but the romantic spark didn't seem to survive the car exhaust and the late-night grocery run. Shortly after, Demi was linked to Trace Cyrus (Miley’s brother), and Cody stayed busy with Dancing with the Stars and his final runs on Hannah Montana.
Where Are They Now?
It’s 2026, and their lives couldn't be more different. Demi Lovato has navigated an incredibly public and often difficult journey through superstardom, recovery, and a return to her rock roots. She's currently engaged to musician Jordan Lutes (Jutes), and they seem incredibly solid.
Cody has stepped back from the massive Disney spotlight. He still acts and does voice work, but he also spends a lot of time teaching. He’s been an acting coach for years, sharing the skills he learned as a child star with the next generation.
Why We’re Still Talking About This
People love this specific "ship" because it represents a very specific, innocent era of pop culture.
- It was before the "Imperial Era" of Disney stars.
- The stakes felt lower.
- The stories were more human.
When Demi faced her well-documented health struggles years later, Cody was one of the first people to publicly send love. He tweeted out his support, proving that even if the dating part didn't work out, that "disaster date" built a foundation of genuine respect.
If you're looking for lessons from the Cody Linley and Demi Lovato saga, it’s basically this: your car breaking down on a first date isn't the end of the world. In fact, if the person stays to help you fix the engine, you've probably found someone worth keeping in your life, even if they don't end up being "the one."
Actionable Insights for Fans and Archive Diggers:
- Check the Source: If you see "quotes" about them dating for years, ignore them. Cody’s 2008 Seventeen interview is the definitive account of their brief time together.
- Look for the Cameos: Cody appeared in several Disney-era vlogs and behind-the-scenes clips from that time; they are a goldmine for seeing their actual friendship dynamic.
- Respect the Evolution: Both artists have moved far past their "teen idol" labels. Supporting their current work (Demi’s music and Cody’s acting workshops) is the best way to be a fan in 2026.