Inside Debby Ryan, Josh Dun's Decade-Long Love Story Now Blossoming Into Parenthood

When Debby Ryan and Josh Dun announced on September 7, 2025, that they were expecting their first child, the internet erupted with joy. In a sweet joint Instagram post, the couple could be seen cradling Debby’s baby bump while Josh held up a tiny pair of checkered Vans. The post was flooded with congratulatory messages from friends and fans alike.

For Debby and Josh, the pregnancy marks a beautiful new chapter in a love story that has spanned nearly over a decade. From their first date in 2013 to their intimate wedding in 2019, the actress and the Twenty One Pilots drummer have built a life rooted in creativity, respect, and love. As they start a new chapter of parenthood, let’s have a look at their relationship timeline.

The first spark between Debby Ryan and Josh Dun

The story began in 2013, when Debby, fresh from her Disney Channel stardom, and Josh, the rising drummer of Twenty One Pilots, went on their very first date. In an Instagram throwback years later, Debbie revealed a charming detail that Josh had learned how to tie a bow tie just for the date. The small but sincere act was something that Debby remembered to this day. In her post, she wrote:

“Thanks for learning how to tie a bowtie for our first date and everything we’ve figured out together since.” 

By September of the same year, Josh confirmed their romance with an Instagram post of the two holding hands against a scenic backdrop. He captioned the post, ‘Trying to help each other not fall off that ledge.’ Fans swooned over the new couple, sensing a young love story that was unfolding before their eyes.

Debby Ryan and Josh Dun went through a breakup only to get back stronger

Like many young couples in the public eye, Debby and Josh’s relationship was not without its challenges. In March 2015, Debby hinted at a breakup in a now-deleted tweet. She wrote, 'Single and not tryna mingle.’ Fans speculated about what went wrong, but both Debby and Ryan kept the details private.

Then, in December 2016, reconciliation rumours began when producer, John Feldmann posted a Christmas party photo featuring Debby and Ryan in matching Santa hats. The sight thrilled their fans, as the couple had found their way back to each other. It was a reunion that would prove to be a lasting one for them.

Debby Ryan and Josh Dun gave love another chance

By 2018, Debby and Josh were not only back together but thriving as well. In interviews, Debby spoke about how much Josh meant to her. Later that year, she confirmed to the Sydney Morning Herald that she is in love and very happy. She said that they are each other’s biggest fans. In an interview with PEOPLE, she could be quoted as saying:

“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.”

Debby Ryan and Josh Dun’s fairytale proposal in New Zealand 

On December 22, 2018, Josh came up with one of the most romantic proposals in celebrity love stories. During a trip to New Zealand, he led Debbie to a treehouse in the woods, went on one knee and popped the question. He even flew in Debby’s brother and sister-in-law to witness the special moment. Debby described the proposal with her signature mix of humour and sincerity. She wrote:

“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.”

Debby Ryan and Josh Dun had a secret New Year’s Eve wedding 

Just a year later, on December 31, 2019, the couple surprised the world by secretly tying the knot in Austin, Texas. Guests thought they were attending a New Year’s Eve party, only to witness Debby and Josh exchange their vows. It wasn’t until May 2020 that the couple confirmed their marriage in an interview with Vogue. Debbie revealed that the sudden death of her close friend, Cameron Boyce made her re-evaluate waiting, and she decided just to do it.

Debby and Josh’s wedding was as unique as they are. She wore an Elie Saab gown, and Josh sported a green velvet Paul Smith suit with Nike Cortez sneakers; their dog, Jim, served as the ring bearer for the couple. Josh told Vogue that it felt like a game night at their house.

Debby Ryan and Josh Dun’s life as husband and wife

From that moment, Ryan and Dun embraced married life with the same candid fun that defined their romance. They celebrated anniversaries with quirky traditions, supported each other’s careers, and eventually built their first home together in Columbus, Ohio. Their house was completed with a boxing ring in the basement and a giant mushroom mural and was featured in Architectural Digest in 2023.

The couple also enjoyed travelling, celebrating holidays with whimsical flair, and time and again they have been seen walking red carpets together. Always playful, Debby and Josh often shared inside jokes with fans online, balancing their fame with a down-to-earth sense of intimacy that the two of them are known for.

Debby Ryan and Josh Dun are expecting a baby

Now, nearly six years after their wedding, Debby and Josh are preparing for their biggest adventure yet: parenthood. The announcement was made through Instagram and shocked the entire world. Debby looked radiant in a white top, cradling her bump. Josh could be seen planting a sweet kiss on her neck while holding up baby shoes.

For fans who have followed their journey from Debby’s Disney Channel days to Josh’s global stardom with Twenty One Pilots, the news feels like the natural next step in a love story that has been defined by love and joy. Fans and friends alike have flooded their comment section with love and congratulations.

Debby and Josh have kept much of their private life sacred, choosing when and how to share moments with the world. As they step into this new role as parents, it’s likely they’ll continue to maintain that balance and cherish their intimacy while letting fans celebrate alongside them.

As they prepare to welcome their first child, their love story is evolving once more into a story of family and the joy of new beginnings.

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