Debby Ryan and Josh Dun's Relationship Timeline

Debby Ryan and Josh Dun began dating in 2013 and got married in 2019

Debby Ryan and Josh Dun have been together for nearly a decade.

The former Disney channel star and the Twenty One Pilots drummer began dating in 2013 and secretly tied the knot on Dec. 31, 2019. Several months later, the couple confirmed that they had wed in an interview with Vogue and shared details of their intimate ceremony, which they had planned in just 28 days.

"[When everyone was in place], I began to hear 'Hoppípolla' by Sigur Rós, and the church doors opened, and I saw him waiting," Ryan recalled of walking down the aisle. "I took in everyone beaming as I moved through the extra-long church, drawn toward my favorite person. When [our officiant] Dave asked who gives me away, my dad responded, 'She does, and we support this decision wholeheartedly,' which brought the first tear to my eye."

Since then, Ryan and Dun have celebrated plenty of milestones as husband and wife, including several anniversaries and designing their first home together in Ohio.

From their stylish first date to a New Zealand treehouse proposal, here is a complete timeline of Debby Ryan and Josh Dun's relationship.

Early 2013: Debby Ryan and Josh Dun go on their first date

In a 2018 Instagram tribute for Dun's birthday, Ryan revealed a few details of their first date, including Dun's sartorial gesture.

"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," she captioned a picture of the two cuddled up at a candlelit table.

September 23, 2013: Debby Ryan and Josh Dun make their relationship Instagram official

Dun confirmed the couple's relationship status on Instagram when he posted a photo of the pair holding hands in front of a scenic background.

"Trying to help each other not fall off that ledge," he wrote in the caption.

March 16, 2015: Debby Ryan hints at split from Josh Dun

The pair had kept the early days of their relationship relatively private, so fans were surprised to learn that Ryan and Dun had broken up. When a fan asked the Jessie actress, "Are you single?" she responded in a since-deleted tweet, per J-14, "Single and not tryna mingle."

December 18, 2016: Debby Ryan and Josh Dun get back together

Rumors of reconciliation began to swirl in December 2016 when music producer John Feldmann posted a Christmas party photo on Instagram that featured Ryan and Dun in matching Santa hats.

The group photo also included Blink-182 drummer Travis Barker among others.

August 10, 2018: Debby Ryan says she and Josh Dun are each other's biggest fans

By August 2018, the couple were stronger than ever. Ryan opened up about their relationship during an interview with PEOPLE and shared that Dun helps her to stay true to herself.

"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."

She continued, "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."

August 19, 2018: Debby Ryan says she is in love with Josh Dun

Later that month, Ryan spoke about her relationship with Dun again with The Sydney Morning Herald.

"I'm in love and very happy," she said. "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."

December 22, 2018: Debby Ryan and Josh Dun get engaged

Dun proposed to Ryan during a December getaway to New Zealand. The drummer also surprised Ryan by flying in her brother and sister-in-law for the occasion. The Insatiable star shared a series of photos documenting the memorable moment. In the snaps, Ryan smiled while Dun was down on one knee and shed a few tears.

"My dude asked me on a date," she wrote. "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."

She added, "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."

Dun also posted about the proposal, writing in the caption: "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."

August 13, 2019: Debby Ryan and Josh Dun take a trip to Europe

In August 2019, Ryan shared a photo of the pair on the tarmac as they headed for a month-long trip to the United Kingdom and Europe.

"Running to eu/uk for a month, y'all need anything? pizza money's on the counter," Ryan captioned the image.

The actress shared how important travel was to their relationship in her 2018 interview with Sydney Morning Herald.

"For as long as we've known each other, travel's been a huge part of it," she said. "I can't wait to visit him this year and have more time to watch him play his drums and to spend more time wandering in Australia and seeing my friends there."

December 31, 2019: Debby Ryan and Josh Dun secretly get married

The couple secretly tied the knot on New Year's Eve in 2019 in Austin, Texas. While they did not publicly confirm the wedding news for several months, Ryan shared a series of black-and-white photos on Instagram from their night, which fans assumed was a New Year's celebration.

She captioned the post: "Got all dressed up and closed out the decade with family and friends ✨little destination celebration party camp as an excuse to finally bring together our core folks from all corners of our worlds ⚡️we danced all night and had milk n cookies and I had the most fun of my life."

May 21, 2020: Debby Ryan and Josh Dun confirm their marriage in Vogue

Ryan and Dun confirmed they wed five months after their secret ceremony in Vogue, sharing photos from their special day and discussing how they planned it in just 28 days.

While the couple were originally going to take their time with the wedding planning and have a longer engagement, the death of Ryan's close friend, Cameron Boyce, changed her mind.

"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," Ryan told Vogue.

They exchanged vows in Austin, Texas, with the bride wearing an Elie Saab gown and the groom decked out in a green velvet Paul Smith suit paired with black Nike Cortez shoes. Their dog Jim served as a ring bearer. After dinner, Ryan changed into an Are You Am I silk slip dress and sneakers so the newlyweds could take to the dance floor.

"The ceremony was the perfect balance," Dun said. "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."

July 5, 2020: Debby Ryan and Josh Dun celebrate their six-month wedding anniversary

In June 2020, the newlyweds and their dog held a six-month anniversary celebration, complete with an assortment of white and gold balloons and a sprinkle-covered cake.

"6 months in with m'bride," Dun wrote on Instagram.

December 25, 2020: Debby Ryan and Josh Dun celebrate their first Christmas as husband and wife

To mark their first Christmas as a married couple, Ryan and Dun posted retro glamour shots from their holiday card photo shoot and words of encouragement for their followers.

"My lover @joshuadun and I invite you to frame this photo in your home (or our holiday card; see his page). In earnest, we are hoping you don't feel alone today," Ryan wrote. "We're hoping you feel joy, peace and purpose. you're here for a reason. in a year that has hunted us all down in a variety of ways and demanded we feel the broadest, most brutal confrontation of experiences, I hope you look to the coming days, know that god doesn't waste pain and feel struck by 'the thrill of hope.'"

Dun shared the same photos on his account, adding, "merry christmas from us to you. what an intense year this has been but we're wishing you the best on this day."

May 13, 2021: Debby Ryan receives sweet tribute from Josh Dun on her birthday

To mark Ryan's 28th birthday, Dun penned a sweet tribute on Instagram to his wife alongside a series of photos of the two together.

"Happy birthday love of my life. Debby constantly makes my life better by being always curious, constantly loving, loyal, friendly and courteous to everyone she's around," he wrote. "Pushes me to be a better human and always makes me feel cooler than i am. love you forever."

May 22, 2021: Debby Ryan celebrates Josh Dun's album launch

Twenty One Pilots dropped their sixth studio album, Scaled and Icy, with an innovative live-streamed event from their hometown of Columbus, Ohio. Ryan was there to support the musical duo and praised Dun on Instagram.

"So proud of my lover and his band's Scaled And Icy album and the incredibly elaborate livestream experience tonight — and grateful to've popped up in the widely coveted role of Woman With Bucket," she wrote in the caption. "So many talented people brought their A game. Scaled And Icy is so good I can't stop listening. huge fan."

May 27, 2021: Debby Ryan and Josh Dun make their red carpet debut as a married couple

Over a year after they said "I do," Ryan and Dun walked the red carpet as husband and wife. The two attended the 2021 iHeartRadio Music Awards in Los Angeles and posed for a photo alongside Dun's bandmate Tyler Joseph and his wife, Jenna. Ryan later posted images from the event on Instagram after fans reminded her of the milestone.

"I'd say one of the things I'm most proud of is making the best person I know My Husband," she captioned the photo. "We've been married for a year and some change now which I know we did on the low, but the internet informed me this was our first time Being On A Red Carpet Whilst Married which I totally knew and that's why I pulled my hair back with a shoelace, so just wanna shout out my life partner and his twenty one pilots partner tyler (big dog of my favorite band) and his life partner jenna, who is subsequently now my Partner In Being Ignored On Stage While They Accept Awards."

December 31, 2021: Debby Ryan and Josh Dun celebrate their second wedding anniversary

As 2021 came to a close, Ryan celebrated her second wedding anniversary with Dun. In honor of the occasion, she posted a photo of herself and Dun in what appeared to be an underwater restaurant.

"Two years ago rn we threw a new year's eve party and got married and went on a honeymoon and it was all ours and it's good," she wrote.

November 5, 2022: Debby Ryan and Josh Dun dress up together for Halloween

For Halloween 2022, Ryan and Dun donned a couples costume, dressing as Julie Andrews and Dick Van Dyke's characters from the 1964 film Mary Poppins.

On Nov. 5, Ryan shared photos from the night on Instagram with the caption: "Halloween at home — a trick and a treat 🎃 no chaos, just togetherness and candy that's it why."

March 21, 2023: Debby Ryan and Josh Dun give Architectural Digest a tour of their home

Keeping in line with their treehouse engagement, Ryan and Dun's home in Columbus, Ohio, has a treehouse theme — complete with a giant mushroom mural and even a boxing ring in the basement.

The couple gave Architectural Digest a tour of their shared space in March 2023 and discussed their design inspiration.

"To be among the trees was really inspiring," Dun said. "This treehouse theme informed a lot of the design sensibility. 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."

Regarding why the couple decided to settle in Dun's hometown, Ryan said, "People often say, 'What's in Ohio?' ... But we're so inspired by this place. Building this home, inviting people into it … the whole process has created a new sense of us."

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