Debby Ryan has always had a knack for connecting with people – first onscreen, and more recently, through her openness about life beyond the spotlight. Born in Huntsville, Alabama in 1993, she quickly made waves as Bailey Pickett on “The Suite Life on Deck,” but it was her starring role on “Jessie” that really made her a household name for a generation of Disney Channel fans. Onscreen, she was instantly relatable, with a sense of humor and vulnerability that stood out even in a sea of talented young actors.
Music has always been a part of Ryan’s life too. She started The Never Ending, a band that let her explore another side of her creativity. Whether performing onstage or stepping behind the scenes as a director, Ryan’s range goes far beyond acting. In recent years, she’s also spoken up about mental health – a move that’s made her voice resonate even more deeply with her young audience. Instead of just sticking to scripted roles, she’s chosen to share her story in her own words, helping fans feel seen and less alone.
From Disney Star to Married Life
While Debby Ryan’s career flourished in the spotlight, her personal life took a quieter path. After years of dating rumors and the usual Hollywood speculation, she surprised everyone by marrying Joshua Dun, the drummer from Twenty One Pilots. The two began dating around 2013, hit a few bumps – as most couples do – and eventually pulled off a remarkably under-the-radar wedding on New Year’s Eve 2019. When she shared photos months later, fans cheered not just for the romance but for the rare feat of privacy in an era of constant sharing.
Looking back, Ryan’s earlier relationships also had a way of flying under the radar. She dated actor Gregg Sulkin for about a year starting in 2009 – a time when both were finding their footing in a tricky industry. There was a brief romance with Sean Marquette that same year, and, yes, plenty of fan speculation about a possible spark with Lucas Till, though the two have always said they were just friends.
If there’s a throughline in Ryan’s love life, it’s how gracefully she’s handled the attention. She never tried to turn breakups or new relationships into headlines. Instead, she set a different kind of example: keep the important stuff close, share what feels right, and don’t let public opinion steer your private life.
In an interview with Teen Vogue back in 2015, Ryan summed it up perfectly: “Love is about growing together, not apart.” That blend of wisdom and sincerity shines through in her relationship with Dun. Both are busy, both have creative streaks – yet they’ve managed to support each other without losing themselves as individuals.
Unlike many of her peers, who sometimes turn their private lives into clickbait, Ryan has always preferred to keep things low-key, rarely speaking about past partners and focusing instead on what she’s building now. It’s clear she gravitates toward creative people who get the weirdness and wonder of the entertainment world, but she also values a kind of maturity and stability that’s rare for someone who grew up in front of the camera.
Past Relationships
Joshua Dun
Lucas Till
Gregg Sulkin
Sean Marquette
Jason Dolley
Now in her late twenties, settled with Dun, Ryan seems happier and more grounded than ever. She’s found a space between public and private that works for her – a space where she can celebrate her achievements, be honest about her struggles, and keep the things that matter most out of the glare of the spotlight. For anyone who grew up watching her, it’s a reminder that it’s possible to grow, change, and find happiness – even when everyone’s watching.