Debby Ryan just got engaged to her boyfriend Josh Dun, and we are so excited for the couple! The two lovebirds actually have a really long history together, and in honor of the exciting news, we decided it’s time to take a walk down memory lane and recap everything they went through as a couple.


The relationship actually dates all the way back to May of 2013. That’s right, that means the couple has been together for more than five years! The pair was low-key at first, but after they made their social media debut in September of 2013, they couldn’t stop sharing their adorable PDA on Instagram.

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trying to help each other not fall off that ledge.

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They were seriously goals! The couple even wore matching outfits, and it couldn’t have been cuter.

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super fancy.

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They were practically inseparable!

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her head is a living forest full of songbirds

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The pair constantly gushed over one another on Instagram, and we were loving it.


But something must have went wrong along the way because in 2015, the Jessie star actually admitted she was single. During a Twitter chat with her fans, she revealed that not only did she not have a guy in her life at the time, but she wasn’t looking for one either. “Single and not tryna mingle,” she wrote.


But then in 2016, Debby and the Twenty One Pilots drummer sparked reconciliation rumors after they were spotted together at a holiday party. Music producer John Feldmann threw the Christmas party, and the pair posed for plenty of pics together, sending fans into a frenzy.

They even wore matching Christmas hats, which is something you only do with someone you really care about, right? It was unclear at the time if they were just friends or if they were back together, but from the pics, they definitely seemed like a couple to us.


Then in June of 2018, rumors started swirling that they were back together again when Deb took to Instagram to share the most precious birthday message to the musician. She posted a pic of the pair on their first ever date, writing, “Hbd, boy. 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.”

And one month later, while speaking to The Sydney Morning Heraldthe actress confirmed that she and Josh were indeed back on and they were happier than ever! “I’m in love and very happy. We’ve evolved and grown so much in our careers, in the relationship, as people since we first met,” she said. “It’s cool and special to have that support system and we are each other’s biggest fans.”

Four months later, on Dec. 22, 2018, the couple announced that they were getting married. “I said yes! Well technically I said ‘NO WAY’ twice but I meant yes,” Debby wrote on Twitter alongside some adorable snaps of the moment her man got down on his knee. Josh asked Debby to marry him in a treehouse in Switzerland (ugh, how romantic is that?), and he even flew her family out to surprise her. After five long years of being on-and-off, the couple has finally found their happily ever after together. You know what they say, what’s meant to be, will be!

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