Debby Ryan and Josh Dun's Relationship Timeline

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

Celebrity engagements are always heartwarming, so when Debby Ryan and Josh Dun announced their engagement in December 2018, we were thrilled! The 25-year-old star of Insatiable has been on and off with the Twenty-One Pilots drummer since 2013, and they seem happier together than ever. The couple don't seem in any rush to get to the altar, instead just enjoying their time together and supporting each other's creative and professional endeavours. Although they've been linked romantically for six years, their relationship hasn't been all smooth sailing. Keep reading for a complete timeline of the important moments in their relationship!

Image Source: Getty / Imeh Akpanudosen

1. September 2013: Debby and Josh 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.

2. March 2014: Debby and Josh Attend a Gala Together

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

Image Source: Getty / Imeh Akpanudosen

3. March 2015: Debby Acknowledges She's Single

It's unclear what, exactly, happened in late 2014 or early 2015, but at some point during that time, Josh and Debby broke up. In March 2015, Debby replied to a fan's tweet and clarified that she was "single and not tryna mingle."

Image Source: Getty / Jeffrey Mayer

4. December 2016: Debby and Josh Pose Together at a Christmas Party

Debby and Josh sparked rumours that their relationship was back on again when they were photographed together at music producer John Feldmann's Christmas party, wearing matching hats.

Watch This!

Pop Quiz

Watch the Cast of Fear Street Play a Creepy Game of Horror Movie "Would You Rather"

5. June 2018: Debby and Josh Reveal They're Back Together

It was over a year before the rumours about Debby and Josh started up again, this time thanks to a very romantic-seeming 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, Debby confirmed they were back together in an interview 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."

6. December 2018: Debby and Josh Announce Their Engagement

Just before Christmas 2018, during a trip to New Zealand, Debby and Josh 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 forever dude," Debby wrote on Instagram. She added, humourously, on Twitter, "I said yes! Well technically I said "NO WAY" twice but I meant yes."

7. October 2019: Still Going Strong

Though Debby and Josh haven't released any details about their marriage plans, they regularly post photos of one another on Instagram. Debby supports Josh on tour, and he helps promote her Netflix series, Insatiable.