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
Related: Debby Ryan Has an Impressive Collection of 6 Tattoos – Here’s What They All Mean
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.
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.”
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.”
