If you’re still searching for "Debby Ryan boyfriend," you’re basically living in 2013. Honestly, it’s understandable. The internet has a long memory, and those early photos of the Jessie star and the guy from Twenty One Pilots are burned into our collective Tumblr-era brains. But the reality is way more domestic—and honestly, a lot cooler—than just a "boyfriend" status.
Debby Ryan isn’t dating. She’s been married to Josh Dun for years, and as of late 2025, they’ve officially entered their "parents" era. It’s a wild transition for anyone who grew up watching her on Disney Channel, but here we are.
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Why Everyone Still Asks About the Debby Ryan Boyfriend Situation
People get stuck on the "boyfriend" thing because their relationship was kind of a rollercoaster at first. They started dating way back in May 2013. Then they broke up. Then they were "just friends." Then they were back on. It was that classic "will-they-won't-they" that keeps fans Googling for updates even a decade later.
But the "boyfriend" title officially died in a New Zealand treehouse.
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In December 2018, Josh Dun—the drummer known for his high-energy performances and ever-changing hair colors—finally popped the question. He didn't just do a standard dinner proposal. He found a literal treehouse in the woods. Debby later joked on Instagram that she technically said "NO WAY" twice before actually saying yes.
The Wedding That No One Saw Coming (Until It Happened)
They didn't wait long. While most celebs spend two years planning a "royal-adjacent" wedding, Debby and Josh pulled theirs together in exactly 28 days.
Why the rush? It wasn't because of a "shotgun" situation. Honestly, it was much heavier than that. Debby shared with Vogue that the passing of a close friend earlier that year changed her perspective. It made her realize that waiting for the "perfect" time is a trap. "Intending to do things is not nearly as powerful as doing," she said.
They tied the knot on New Year’s Eve 2019 in Austin, Texas. It was a whole vibe:
- The Dress: A stunning, architectural Elie Saab gown.
- The Groom: Josh rocked a green velvet Paul Smith suit with black Nike Cortez sneakers.
- The Guest of Honor: Their dog, Jim, was the ring bearer.
They kept it so quiet that fans didn't even know they were officially hitched until months later when Josh appeared in the "Level of Concern" music video wearing a wedding ring.
The 2026 Reality: Meet Felix Winter Dun
If you’ve missed the news lately, the "Debby Ryan boyfriend" searches are now being replaced by baby name searches. On December 13, 2025, the couple welcomed their first child.
Her name is Felix Winter Dun.
Debby didn't go the traditional hospital route. She opted for an intimate home birth. She described the experience on Instagram as being "fortified by an incredible birth team" and joked that Josh was a "great teammate" who managed not to drown in the birthing tub. It’s a far cry from the red carpets and flashy tour buses.
What Most People Get Wrong About Their Relationship
- The Age Gap: People always freak out about this, but it’s actually pretty standard for Hollywood. Josh is 37 and Debby is 32. That five-year gap seemed bigger when she was a Disney teen, but now they’re just two adults living in Ohio.
- The "Secret" Breakups: They’ve been together for over a decade, but it hasn't been a straight line. They split for a significant chunk of 2014 and 2015.
- The Ohio Move: You’d expect them to live in a glass mansion in the Hollywood Hills. Nope. They live in Columbus, Ohio. They even did an Architectural Digest tour of their house, which features a boxing ring in the basement and a massive mural of a mushroom.
Actionable Takeaways for Fans
If you're following their journey or looking for how they’ve managed to stay together in the messy world of entertainment, there are a few real-world lessons here.
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- Prioritize Privacy: They didn't announce the wedding for five months. They didn't announce the pregnancy until Debby was significantly far along. Keeping the "sacred" stuff off social media seems to be their secret sauce.
- Embrace the "Pivot": They went from a long-distance rockstar/actress dynamic to a quiet life in the Midwest. They didn't let their 2013 "brand" dictate their 2026 reality.
- Focus on Friendship: Debby frequently calls Josh her "best person" and "dude for life."
The "boyfriend" era is long gone. Whether you're a fan of Twenty One Pilots or a Jessie nostalgist, the Debby and Josh story is now officially a family saga. If you want to keep up with them, look for updates on Felix and their life in Columbus rather than checking for new "dating" rumors. They’ve clearly found their "forever" version of the relationship.