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

Getty / Bryan Bedder

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

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