From Secret Dates to Shared Parenthood: The Enduring Love Story of Josh Dun and Debby Ryan

Josh Dun, the dynamic drummer of the acclaimed musical duo Twenty One Pilots, has captivated audiences not only with his percussive prowess but also with his public and enduring romance with actress Debby Ryan. Their love story, spanning over a decade, has unfolded through various chapters, marked by public affection, a brief separation, a fairytale proposal, a secret wedding, and most recently, the joyous anticipation of parenthood. Their journey together reflects a deep connection built on mutual respect and shared experiences, evolving from young love into a profound partnership.Their romantic narrative began to publicly emerge in 2013, when Debby, known for her Disney Channel roles, and Josh, then a rising star in the music scene, embarked on their first date. A charming detail shared by Ryan years later revealed that Dun had learned to tie a bow tie specifically for their initial outing, a gesture that left a lasting impression. By September of that year, Josh publicly confirmed their budding romance with an Instagram post featuring the couple holding hands, captioning, "Trying to help each other not fall off that ledge," signaling the start of a much-watched relationship.Like many relationships in the public eye, their journey faced its challenges, leading to a brief separation. In March 2015, Debby hinted at a breakup with a now-deleted tweet stating, "Single and not tryna mingle," leaving fans to speculate about the reasons behind their split. However, the story of Josh Dun and Debby Ryan was far from over, as reconciliation rumors began to surface in December 2016 when a producer shared a Christmas party photo showing the pair together in matching Santa hats, much to the delight of their fanbase.By 2018, the couple was not only firmly back together but openly thriving, with Debby frequently speaking about the depth of her feelings for Josh. She confirmed to the Sydney Morning Herald that she was "in love and very happy," emphasizing that they were each other's biggest supporters. In an interview with PEOPLE, Ryan articulated the importance of their bond, stating, > "It’s really key to be with someone who respects you and likes you for who you are…When you’re dating someone who you think is awesome and is your best friend, you just bring each other up."Their relationship reached a significant milestone on December 22, 2018, when Josh orchestrated a truly romantic proposal during a trip to New Zealand. Leading Debby to a secluded treehouse, he got down on one knee and asked her to be his wife, even flying in her brother and sister-in-law to witness the special moment. Debby beautifully captured the essence of the proposal on social media, writing, > "My dude asked me on a date … then he asked me to be his dude forever. He’s my heart outside my body. He’s a cold water awakening and a warm bed; he’s the place I can rest."Just over a year later, on December 31, 2019, Josh Dun and Debby Ryan surprised the world by secretly tying the knot in Austin, Texas. Guests, initially believing they were attending a New Year's Eve party, instead witnessed the couple exchange vows in an intimate ceremony. The decision to marry discreetly was later revealed by Debby in a May 2020 interview with Vogue, where she shared that the sudden death of a close friend had prompted her to re-evaluate waiting and simply "do it."The wedding itself was a reflection of their unique personalities, with Debby wearing an elegant Elie Saab gown and Josh opting for a green velvet Paul Smith suit paired with Nike Cortez sneakers. Their beloved dog, Jim, played a special role as the ring bearer, adding a personal touch to the celebration. Josh described the atmosphere to Vogue, saying it felt like "a game night at their house," highlighting the relaxed and joyful nature of their union.Since their wedding, Ryan and Dun have embraced married life with their characteristic blend of candid fun and genuine affection. They have built their first home together in Columbus, Ohio, a unique space featuring a boxing ring in the basement and a giant mushroom mural, which was notably featured in Architectural Digest in 2023. The couple frequently shares glimpses of their life, from quirky anniversary celebrations to public appearances, balancing their individual fame with a down-to-earth intimacy that resonates with their fans.In a heartwarming development, the couple announced on September 7, 2025, that they are expecting their first child. The news, shared via a joint Instagram post, featured Debby cradling her baby bump while Josh held up a tiny pair of checkered Vans, symbolizing their excitement for their expanding family. This announcement marks a beautiful new chapter in their decade-long love story, evolving into parenthood and further solidifying their enduring bond.Josh Dun and Debby Ryan's journey from initial dates to a loving marriage and now impending parenthood exemplifies a modern romance that has navigated the complexities of public life with grace and authenticity. Their story is a testament to finding a partner who is both a best friend and a steadfast support, continually bringing each other up. As they prepare to welcome their child, their love story continues to unfold, inspiring fans with its genuine connection and joyful evolution.