Actress Debby Ryan and musician Joshua Dun, drummer of the Grammy Award-winning band Twenty One Pilots, have announced they are expecting their first child together, marking a major milestone in a relationship that has lasted over ten years.On September 7, 2025, the couple shared the news in a joint Instagram post featuring maternity photos and a sonogram, captioned:"dun&dun +one."Debby Ryan, best known for her role on the Disney Channel series Jessie, has been in a relationship with Dun since 2013, although there was a brief separation in the early years of their relationship. View this post on Instagram Instagram PostTheir journey has been mostly private. They had a secret marriage in Austin, Texas, on December 31, 2019, following Dun's highly publicized proposal the previous year. With the announcement of their pregnancy, renewed interest has emerged in the timeline of their relationship and the development of their personal lives, from their first date in 2013 to the present day.The start of Debby Ryan and Josh Dun’s RelationshipDebby Ryan and Josh Dun's relationship began in 2013. In a 2018 reflective birthday Instagram throwback, Ryan reminisced about their first date and directly addressed Dun, saying:“hbd, boy. thanks for learning how to tie a bowtie for our first date and everything we’ve figured out together since. you were only 24 here, before I dyed your hair and you taught me love.”2021 MTV Video Music Awards - Arrivals (Image via Getty)Two years into the relationship, Debby Ryan confirmed she was single, signaling a temporary separation from Dun. In a conversation, when a fan asked, "Are you single?" she responded in a deleted tweet: "Single and not tryna mingle." The remark made it clear she had separated from Dun by that time, but neither of them provided any additional details about the split publicly.Debby Ryan and Josh Duns' reconciliation and strengthening of their partnershipBy the end of 2016, signs of reconciliation began to emerge. Later that year, Ryan and Dun appeared together at a Christmas party, both wearing identical Santa hats. Their joint appearance sparked speculation that they had gotten back together after breaking up in 2015. In August 2018, Debby Ryan publicly discussed her relationship with Dun in an interview with PEOPLE magazine, offering rare insight into their bond."I think it's really key to be with someone who respects you and likes you for who you are, and honestly makes it attractive to do things you want to be," she said. "To take up a new hobby and push yourself. When you're dating someone who you think is awesome and is your best friend, and they're constantly like, 'I'm gonna go for a run. Do you want to go?' And you're like, 'I was just thinking that!' You just bring each other up. So I think staying genuine and having girlfriends and prioritizing having your own life and being each other's biggest fan."In December 2018, Dun proposed to Ryan on a trip to New Zealand. On Instagram, Ryan wrote:"My dude asked me on a date. I said yeah because I always want to go on dates with him. Then he asked me to be his dude forever. He does things well, and right. His timing has pressed us and never failed us."He's my heart outside my body. He's a cold water awakening and a warm bed; he's the place I can rest. Dudes for life. It was a really good date."Josh also posted on the occasion, expressing:"I found a tree house in the woods in New Zealand and proposed to my girl. She my dude for life. I love you Debby."pop culture @postbestfshnLINKDebby Ryan and Josh Dun have announced their engagement 💍The couple got married a little over a year later, on December 31, 2019, in Austin, Texas. They planned the wedding in less than a month and kept it private until Debby Ryan confirmed it during an interview with Vogue. Reflecting on their decision to marry quickly after the death of Ryan's close friend, Cameron Boyce, Ryan said:"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."Debby Ryan's Instagram post (Image via Instagram/@debbyryan)Years after their marriage, in 2023, Ryan and Dun gave fans a glimpse into their personal lives by inviting Architectural Digest into their home in Columbus, Ohio. Their treehouse-style house, featuring organic shapes, their own artwork, and even a boxing ring, was said to reflect their ongoing creativity and unique style. In 2025, Debby Ryan and Dun announced they were expecting their first child. The news was celebrated by fans as a new chapter in the couple's long-lasting relationship.Stay tuned for more updates.