When you think of celebrity weddings, images of grand, publicized events with red carpets and exclusive magazine deals might come to mind. But for Debby Ryan and Josh Dun, their journey to “I do” was a beautifully kept secret that perfectly reflected their unique bond. The former Disney Channel star and the Twenty One Pilots drummer managed to pull off a stunning New Year’s Eve celebration in Austin, Texas, with a planning timeline that would give most wedding planners heart palpitations—just 28 days. This wasn’t just another Hollywood union; it was a deliberate, intimate, and deeply personal declaration that broke all the conventional rules.
The story of Debby Ryan wedding festivities is more than a checklist of a beautiful dress and a cool venue. It’s a narrative about perspective, born from personal loss, and a conscious choice to prioritize lived joy over perfect planning. It’s about a couple who envisioned their celebration not as a staged performance for public consumption, but as an authentic extension of their relationship—a “game night at our place” that somehow evolved into a “Gatsby-level dance party”. From a whimsical treehouse proposal in New Zealand to exchanging vows as the clock struck midnight on a new decade, every step of their journey was infused with intention and a touch of rebellious charm. Let’s pull back the curtain on one of the entertainment world’s most sweetly secretive weddings and explore how Debby and Josh crafted a celebration that was entirely, unmistakably them.
The Backstory: From First Date to “Dudes for Life”
Long before the wedding bells (or more fittingly, the New Year’s Eve party horns) chimed, Debby Ryan and Josh Dun were writing a low-key love story that fans watched unfold in glimpses. Their origin tale is refreshingly normal for two people who grew up in the spotlight. They were introduced through a mutual friend, a classic setup that led to a first date where, as Debby fondly recalled, Josh learned how to tie a bow tie just for the occasion. They made their relationship Instagram-official in September 2013 with a simple, sweet photo of them holding hands, captioned by Josh: “Trying to help each other not fall off that ledge”. This tone of playful support and partnership would become a hallmark of their relationship.
Their path wasn’t without its turns. Like many couples, they experienced a period of being “on and off,” with Debby even hinting at being single in a since-deleted tweet in 2015. However, by 2016, they were clearly back together and stronger, appearing in matching Santa hats at a holiday event. The time apart seemed to solidify their connection. In a 2018 interview, Debby opened up about their growth, saying, “I’m in love and very happy… We’ve evolved and grown so much in our careers, in the relationship, as people since we first met. It’s cool and special to have that support system, and we are each other’s biggest fans”. This foundation of mutual admiration and evolution was the bedrock upon which they would build their future, setting the stage for a Debby Ryan wedding that was less about a single day and more about the culmination of a lasting partnership.
The chapter that truly sealed their fate began in December 2018. While on a trip to New Zealand ahead of a Twenty One Pilots tour, Josh orchestrated a proposal story that sounds like it’s straight out of a fairy tale—or at least a very cool indie film. He had secretly designed an engagement ring with a friend, but a logistical race against time ensued to get it to New Zealand. The ring was hand-delivered through a series of friendly couriers—from the designer to Debby’s brother, Chase, who then flew it from Los Angeles to Auckland. Josh had scouted a location: a picturesque treehouse nestled in the woods. He secretly dispatched a photographer and videographer to hide and capture the moment he got down on one knee.Debby Ryan Wedding
“The whole operation was a masterpiece of last-minute coordination. Josh later reflected, ‘So many things had to fall perfectly into place, and they all did at the very last second. I couldn’t have imagined the proposal working out any better'”. Debby’s reaction was pure, unfiltered joy. “It was wild and perfect,” she said. “I’m pretty nosy, but didn’t suspect a thing”. She announced the news by saying she technically said “NO WAY” twice before saying yes. Josh called her his “dude for life”, a phrase that would come to define their unconventional and fiercely loyal bond. With the engagement sealed in a treehouse, the next step was to plan a celebration that matched the unique magic of their beginning.
The Whirlwind Decision: Why a 28-Day Wedding Plan?
The typical engagement period involves years of Pinterest boards, venue tours, and slow, meticulous planning. Debby Ryan and Josh Dun threw that playbook out the window. After getting engaged in December 2018, they spent nearly a year as fiancés before the sudden, whirlwind decision to get married on the last night of the decade. What prompts a couple to plan a full-blown Debby Ryan wedding in less than a month? For them, it was a profound shift in perspective triggered by life’s fragility.
The catalyst was the heartbreaking loss of a close friend in the summer of 2019. This loss deeply affected Debby Ryan Wedding, reshaping her outlook on life and time. She explained this pivotal moment to Vogue: “He was excited that Joshua and I were getting married, and I never doubted that I’d know him through every coming phase of our lives… When he passed, it really rocked me and put a lot of things in perspective. It didn’t feel important to wait anymore, to stop being busy, or for things to line up perfectly—intending to do things is not nearly as powerful as doing, as we aren’t promised tomorrow”. This raw realization cut through any desire for a prolonged, “perfect” planning process. The impulse was to celebrate love and life now, with the people who mattered most.
Armed with this new clarity, the concept for their celebration crystallized quickly. “We began to flirt with the idea of having a destination party celebrating the new decade,” Debby said. “Then [we] decided in December to get married on New Year’s Eve, and just keep dancing until after the ball dropped”. The vision was clear: a fusion of an intimate, meaningful ceremony and an epic, joy-filled party. They chose Austin, Texas, as their destination—a vibrant city that offered both reverence and revelry. The mission was to execute a wedding that felt authentic, not curated; alive, not staged. The insane 28-day timeline wasn’t a stressor; it was a liberating constraint that forced them to focus only on what was truly essential to their celebration. It was the ultimate test of their vision and the team they would assemble to bring it to life.Debby Ryan Wedding
Key Factors Leading to the 28-Day Wedding Plan
| Factor | Description | Impact on Wedding Plans |
|---|---|---|
| Personal Loss | The passing of a close friend in summer 2019. | Created urgency & a new perspective on celebrating life immediately. |
| Philosophical Shift | Realization that “intending to do things is not nearly as powerful as doing”. | Moved them from planning to action, rejecting the “perfect” timeline. |
| Celebratory Vision | Desire to merge a wedding with a New Year’s Eve decade celebration. | Provided a natural, festive deadline (December 31, 2019). |
| Logistical Focus | Need to book vendors & venue for a major holiday quickly. | Made a decisive, expert planner (Alex Moreau) absolutely critical. |
Crafting the Vision: “Game Night Meets Gatsby”
With the “why” firmly rooted in emotion and the “when” set as a fast-approaching deadline, Debby and Josh turned to the “how” and the “what.” What does a wedding that’s planned in 28 days actually look like? For this creative couple, it was an aesthetic and experiential fusion that defied easy categorization. Debby perfectly encapsulated the desired vibe: “We wanted it to feel like game night at our place had [turned into] a Gatsby-level dance party”. This single sentence became the north star for the entire event—a blend of intimate comfort and extravagant celebration, of casual friendship and dazzling art deco glamour.
To translate this unique vision into reality, they needed a planner who could operate at their speed and wavelength. Enter Alex Moreau of XO Moreau. Debby had done her homework, speaking to planners for nearly a year, but it was Alex’s proactive energy that won her over. “I’d met and had conversations for almost a year with a handful of the chicest recommended planners and teams from all over,” Debby recalled. “They all seemed capable of throwing a beautiful wedding, but no one else put me into action like Alex”. After a single long coffee meeting on December 2nd, the team decided they could pull off the impossible. Alex became the essential “touchstone of how realistic to stay” while helping Debby navigate “how big I could dream, how unconventional to skew”. This partnership was the first critical piece of the puzzle.
The venue hunt was equally intentional. For the ceremony, they sought sanctity over spectacle. “We didn’t want the ceremony to be in a ballroom,” Debby emphasized. “It became more and more important to us that the sanctity of the union exist in a reverent place”. They looked at churches all over Austin, with Josh ultimately choosing the final one based on its stunning stained-glass windows. For the reception and the all-important party, they selected the Hotel Van Zandt. The hotel’s layout was perfect for their dynamic party flow, featuring multiple ballrooms with floating walls that could open up to create one large space. It allowed guests to “change for dancing, take a disco nap, and come and go at their leisure,” making the whole weekend feel like a relaxed, exclusive takeover by their favorite people. The stage was now set—a reverent church and a flexible, stylish hotel—for a celebration that would seamlessly move from solemn vows to a dance floor that rocked into the new decade.
https://headlinenest.com/keon-coleman-injury/
The Style Files: Fashion, Florals, and Personal Touches
If the venue set the stage, the fashion and decor were where Debby Ryan Wedding and Josh Dun’s personalities truly took center stage. Their choices reflected a harmonious blend of high-end elegance and grounded, cool personal style, perfectly embodying that “high-low” mix they cherished. For Debby, the dress was a non-negotiable dream. She had her heart set on an Elie Saab gown long before the wedding was even a concrete plan. “The day the collection dropped on Vogue, I saved it,” she said. “For a long time, it was the only image of a wedding dress I had saved anywhere”. The final choice was a breathtaking satin, off-the-shoulder design with a cinched bodice and an elaborate skirt—simultaneously classic and fashion-forward.
Josh’s style mission was equally specific and bold. He knew he wanted an emerald green velvet suit, a rich and unconventional choice that immediately set him apart. He turned to his friend Alex, the same collaborator who helped design the engagement ring. “An hour later, he called me back and said he was having a Paul Smith suit shipped,” Josh recounted. He tried it on and knew instantly it was the one. He paired this luxurious jacket with a touch of streetwise cool: black Nike Cortez sneakers. This single detail—the sneakers—said everything about their approach. This wasn’t a wedding where style was stiff or performative; it was about feeling like themselves, ready to dance all night. The complementary looks of the elegant Elie Saab gown and the vibrant Paul Smith velvet suit created a visual dialogue that was both stunning and deeply representative of them as individuals and a pair.
Beyond their own attire, Debby Ryan Wedding was deliberate about curating a team and atmosphere that felt authentic. She intentionally sought out “local, female-owned small businesses” for her professional vendor team. A standout collaborator was Twyla of Remi+Gold Floral Atelier. Debby praised her florist’s ability to translate an “obscure collection of style/vibe references” into stunning arrangements. “She got that I wasn’t attracted to ‘pretty,’ and went straight for beautiful, while keeping it clean and cool,” Debby said. The floral brief was “moody—but make it clean and cool,” with splashes of neon and vibrant pinks against a deep, dark, art deco-inspired palette. The result was far from traditional romantic bouquets; it was atmospheric, edgy, and perfectly in sync with the overall “goth flowers” and “art deco treehouse” aesthetic Debby had envisioned.
Personal, meaningful moments were woven throughout the day. Their dog, Jim, served as the ring bearer, adding a touch of home and humor. One of the most poignant touches came during the ceremony. When the officiant asked, “Who gives this woman away?” Debby’s father responded, “She does, and we support this decision wholeheartedly”. This modern, empowering twist brought the first tear to Debby’s eye and underscored the theme of active, chosen commitment that defined their entire approach to the Debby Ryan wedding. From the macro choices of designer fashion to the micro details of a father’s words, every element was a conscious expression of their shared identity.
The Celebration: Ceremony, Reception, and a Night to Remember
December 31, 2019, arrived, and the secret celebration Debby Ryan and Josh Dun had meticulously crafted in 28 days sprang to life. The day unfolded as a perfect crescendo from intimate solemnity to unrestrained joy, exactly as they had hoped. The ceremony, held in the chosen Austin church with its beautiful stained glass, set a tone of reverence and deep personal commitment. They wrote and recited custom vows to each other, making the moment uniquely theirs. Josh’s recollection of the ceremony captures its magic: “I felt like it was game night at our house, and this was the ultimate game, and boy did I win! I remember every detail from how it felt to be walking down the aisle, to the full body chills I got watching Debby walk down toward me”. It was the intimate, heartfelt “game night” beginning before the “Gatsby-level” party commenced.Debby Ryan Wedding
The transition from ceremony to reception was where their eclectic vision truly came alive. The celebration moved to the Hotel Van Zandt, which had been transformed. The space cleverly used floating walls to connect ballrooms, creating a fluid environment where dinner, toasts, and dancing could intermingle. The fusion of styles was immediately apparent in the entertainment. The evening kicked off in a way few weddings do: with a strings section playing a solemn, beautiful rendition of Coolio’s “Gangsta’s Paradise” as the ceremony began. This bold, unexpected choice signaled to guests that this would be no ordinary event. Later, the energy shifted entirely as DJ Mel took over, fueling a dance party that lasted well past midnight.
The reception was a feast for the senses, designed for fun and interaction. A photo booth provided silly mementos. In a brilliantly whimsical catering choice that again highlighted their “high-low” philosophy, the late-night snack served to guests was milk-and-cookie shooters. Imagine the scene: guests in their formal attire, dancing in a chic, art deco-inspired space, and pausing to sip sweet, nostalgic shooters. It was this kind of detail that made the party feel personally curated and genuinely fun. As the clock struck midnight, Debby and Josh, along with their closest family and friends, welcomed not just a new year but a new decade, and the first moments of their married life together, on a dance floor buzzing with pure celebration. The secret Debby Ryan wedding was a triumphant success, a night that balanced sacred promise with legendary party energy, exactly as they dreamed.
Life After “I Do”: Building a Family and a “Tree Home”
The story of Debby Ryan wedding is a beautiful capsule in time, but the marriage that began that night has continued to blossom in deeply meaningful ways. After successfully keeping their wedding a secret for nearly five months, they finally revealed the news to the world via Vogue in May 2020. Since then, their journey has been one of continued creative collaboration, mutual support, and the building of a life that mirrors the whimsical and authentic spirit of their wedding day.
A key symbol of their life together is their home. In a beautiful full-circle moment that connects back to Josh’s treehouse proposal, they designed and built what they call their “tree home” in Josh’s hometown of Columbus, Ohio. Working with interior designer Fawn Galli, they filled the space with organic shapes, textures, and lush greenery. “This treehouse theme informed a lot of the design sensibility,” Debby told Architectural Digest. “We wanted to soften the lines of the house with organic shapes, textures, and materials. We gravitated toward a lot of green—that’s how the tree house became a tree home”. For Josh, this project was profoundly significant: “Not only was this the first house that we designed together, but it was really the first time that both of us felt the freedom to put our mark on a place”. Their physical home became a testament to their shared vision and growth.
The most exciting new chapter began in September 2025, when Debby and Josh jointly announced on Instagram that they were expecting their first child. The announcement, captioned “Dun&dun +one,” was met with an outpouring of joy from fans. Then, in December 2025, they welcomed their daughter, Felix Winter Dun. Debby Ryan Wedding shared a heartfelt post about the birth, praising Josh: “Joshua was an incredible teammate, and somehow didn’t get pulled into the tub and drowned and is taking such good care of his girls on this side of things”. The use of “teammate” echoes the supportive, partnership-driven language that has always defined their relationship. From secret wedding to public parenthood, their path has been marked by a consistent thread of intentionality, love, and building a life that feels genuinely their own, far from the Hollywood glare.
Conclusion
The Debby Ryan wedding was far more than a celebrity gossip headline or a fleeting social media moment. It stands as a powerful testament to a modern approach to love and commitment—one that prioritizes authenticity over pageantry, meaningful experience over extravagant display, and the courage to follow one’s own timeline. In planning a profound celebration in just 28 days, driven by a renewed perspective on life’s preciousness, Debby Ryan and Josh Dun taught us that a wedding’s value isn’t measured in months of planning or dollars spent, but in the depth of intention behind it.
Their story, from a treehouse proposal in New Zealand to a secret New Year’s Eve party in Austin and finally to building a “tree home” and family in Ohio, is a cohesive narrative about choosing your own path. It’s about blending high fashion with Nike sneakers, solemn vows with “Gangsta’s Paradise,” and intimate game-night vibes with Gatsby-esque revelry. The Debby Ryan wedding ultimately succeeded because every element, from the grand vision down to the milk-and-cookie shooters, was a reflection of two unique individuals coming together as a unified, joyful, and steadfast team. It remains an inspiring blueprint for anyone looking to craft a celebration that is, above all else, unmistakably and authentically their own.
Frequently Asked Questions
How did fans find out about Debby Ryan and Josh Dun’s wedding?
Fans discovered that the Debby Ryan wedding had taken place nearly five months after the fact. The couple secretly married on New Year’s Eve 2019 and successfully kept it private until May 2020. They chose to reveal their marriage in a high-profile feature with Vogue magazine, which published exclusive details and photos of their Austin celebration. Prior to the official announcement, eagle-eyed fans had begun to speculate after noticing Josh wearing a ring in the April 2020 Twenty One Pilots “Level of Concern” music video.
What was unique about the planning of their wedding?
The most unique aspect was the extraordinarily short, 28-day planning timeline. This whirlwind decision was sparked by a personal loss, which gave the couple a new perspective on seizing the moment. They wanted a “destination party celebrating the new decade” that doubled as their wedding. The entire process was fueled by a clear, unified vision described as “game night at our place” meeting a “Gatsby-level dance party,” which guided all their quick decisions.Debby Ryan Wedding
Where did Debby Ryan get her wedding dress?
Debby Ryan wore a custom-designed gown by renowned Lebanese fashion house Elie Saab. She had fallen in love with the design long before the wedding was planned, saving a photo from the collection the day it debuted on Vogue’s website. The dress was a satin, off-the-shoulder design with a cinched bodice and a full, elaborate skirt, embodying a perfect blend of classic elegance and modern glamour for her Debby Ryan wedding.
Did Debby Ryan and Josh Dun have a wedding theme?
While not a single, strict theme, the wedding had a very strong and cohesive aesthetic vision. The couple and their planner, Alex Moreau of XO Moreau, described the vibe as “moody—but make it clean and cool,” with an art deco influence. Debby’s own references included “art deco treehouse” and “goth flowers”. The experiential goal was to blend an intimate, comfortable feel with extravagant celebration, hence the guiding principle: “We wanted it to feel like game night at our place had [turned into] a Gatsby-level dance party”.
Are Debby Ryan and Josh Dun still married and do they have children?
Yes, Debby Ryan Wedding and Josh Dun are happily married. They have continued to support each other’s careers and frequently share loving tributes to one another on social media, especially around anniversaries and birthdays. In September 2025, they announced they were expecting their first child. Their daughter, Felix Winter Dun, was born in December 2025. The couple lives in a custom-designed home in Columbus, Ohio, which they fondly refer to as their “tree home”.
