A Complete Timeline of Debby Ryan and Josh Dun's Relationship

Debby Ryan and Josh Dun have been going strong for nearly a decade now. The "Shortcomings" star, 30, and the Twenty One Pilots drummer, 35, first got together in 2013 and dated off and on for about five years before taking the next step in their relationship. In December 2018, the pair officially got engaged when Dun popped the question in New Zealand. Then, after much speculation from fans, the couple revealed to Vogue that they secretly tied the knot on New Year's Eve in 2019.

Since then, the couple have stayed fairly low-key, though they occasionally show off their romance on social media. For Valentine's Day this year, Ryan shared a sweet photo series of the couple on Instagram simply captioned, "❤️‍🔥🧳💌🧺🥊 Better & better." A month later, she and Dun opened up their Cleveland, OH, home for an Architectural Digest tour.

Although the couple have celebrated some cute milestones over the years, it seems their romance hasn't been all smooth sailing. Keep reading ahead for a complete timeline of all the important moments in their relationship.

Additional reporting by Kelsie Gibson and Njera Perkins


September 2013: Debby Ryan and Josh Dun Make It Instagram Official

Reportedly, the duo began dating a few months earlier, in May 2013, but they didn't make it public until September, when they began showing up regularly on each other's social media pages.

March 2014: Debby Ryan and Josh Dun Attend a Gala Together
Getty | Imeh Akpanudosen

March 2014: Debby Ryan and Josh Dun Attend a Gala Together

About a year into their relationship, Ryan and Dun made a rare joint red carpet appearance at the 2nd Annual Norma Jean Gala.

March 2015: Debby Ryan Reveals She's Single
Getty | Jeffrey Mayer

March 2015: Debby Ryan Reveals She's Single

It's unclear what exactly happened in late 2014 or early 2015, but at some point during that time, the couple seemingly broke up. In March 2015, Ryan replied to a fan's message online and clarified in a since-deleted tweet that she was "single" but "not tryna mingle."


December 2016: Debby Ryan and Josh Dun Pose Together at a Christmas Party

Ryan and Dun sparked reconciliation rumors when they were photographed together at music producer John Feldmann's Christmas party wearing matching hats.


June 2018: Debby Ryan and Josh Dun Reveal They're Back Together

It was over a year before the romance rumors about Ryan and Dun started up again, this time thanks to a very romantic post she shared for his birthday. "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," her caption read.

A few months later, in August, the actor confirmed they were back together in an interview with the Sydney Morning Herald. "I'm in love and very happy," Ryan 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 2018: Debby Ryan and Josh Dun Announce Their Engagement

Just before Christmas 2018, during a trip to New Zealand, the pair shared the news of their engagement on social media. "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," Ryan wrote on Instagram. She added humorously in a since-deleted tweet, "I said yes! Well technically I said 'NO WAY' twice but I meant yes."


December 2019: Debby Ryan and Josh Dun Get Married

In January 2020, Ryan shared a photo from the couple's New Year's Eve party, but little did fans know that it was actually from their wedding. In a May 2020 interview with Vogue, the pair confirmed that they secretly tied the knot on New Year's Eve in Austin, TX.

After a close friend of Ryan's died, the couple decided that they didn't want to wait to get married and planned their wedding in 28 days. "The time just felt right," Ryan told 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."


July 2020: Debby Ryan and Josh Dun Celebrate 6 Months of Marriage

The married pair threw an intimate party with what appears to be just the two of them and their dog six months after tying the knot. "6 months in with m'bride," Dun captioned an Instagram post, which included photos of them posing with balloons and a cake with a "1/2" sign stuck in the middle.

May 2021: Debby Ryan and Josh Dun Make First Red Carpet Appearance as a Married Couple
Getty | Emma McIntyre

May 2021: Debby Ryan and Josh Dun Make First Red Carpet Appearance as a Married Couple

Over a year after secretly tying the knot, the couple made their red carpet debut as a married pair at the 2021 iHeartRadio Music Awards. Ryan acknowledged the milestone in a May 30 Instagram post captioned, "I'd say one of the things I'm most proud of is making the best person I know My Husband. 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 2021: Debby Ryan and Josh Dun Celebrate Second Wedding Anniversary

At the close of 2021, Ryan celebrated two years of marriage with Dun on Instagram by posting a photo of the two at what looks like an underwater restaurant. She captioned it, "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 ✨🕊."