The Ultimate Timeline: 5 Shocking Secrets About Josh Dun And Debby Ryan’s Decade-Long Love Story (Updated 2025)

The power couple of rock and screen, Josh Dun and Debby Ryan, have officially entered their most exciting chapter yet. The Twenty One Pilots drummer and the former Disney Channel star have maintained one of Hollywood’s most private and enduring relationships for over a decade, but as of December 2025, their world has changed forever with the birth of their first child. This article delves into the full, updated timeline of their romance, from their first date to their secret wedding and the new life they have welcomed into their family.

The couple, who have navigated the intense spotlight of the music and acting industries, have a love story filled with on-again, off-again periods, a surprise engagement, and a highly secretive wedding that only came to light months after the fact. Their journey is a testament to finding lasting love amidst global fame, culminating in the joyous announcement that has captivated fans worldwide.

Complete Biography and Professional Profiles

Before diving into their relationship timeline, it is essential to understand the individual careers that brought these two creative forces together. Both Josh Dun and Debby Ryan are established figures in their respective fields, contributing to their combined estimated net worth of approximately $20 million.

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Josh Dun (Joshua William Dun)

• Full Name: Joshua William Dun
• Date of Birth: June 18, 1988
• Place of Birth: Columbus, Ohio, U.S.
• Profession: Musician, Drummer, Songwriter
• Primary Entity: Twenty One Pilots (alongside Tyler Joseph)
• Career Highlights: Joined Twenty One Pilots in 2011, contributing to hit albums like Vessel, Blurryface, and Trench. Known for his energetic, dynamic drumming style and signature red beanie.

Debby Ryan (Deborah Ann Ryan)

• Full Name: Deborah Ann Ryan
• Date of Birth: May 13, 1993
• Place of Birth: Huntsville, Alabama, U.S.
• Profession: Actress, Singer-Songwriter, Director
• Primary Entities: Disney Channel (Jessie, The Suite Life on Deck), Netflix (Insatiable)
• Career Highlights: Rose to prominence as Jessie Prescott on the hit Disney sitcom Jessie (2011–2015). Also known for her leading role as Patty Bladell in the dark comedy series Insatiable (2018–2019).

The Decade-Long Romance: A Detailed Relationship Timeline

Josh Dun and Debby Ryan’s relationship is a modern Hollywood fairy tale, characterized by maturity, independence, and a desire for privacy. Their connection has spanned over 12 years, evolving from a casual romance to a lifelong commitment.

2013: The First Date and Early Romance

The couple first met and began dating in 2013. Their early relationship was notably on-again, off-again, a period that both have since acknowledged as necessary for their individual growth. This early phase, marked by their young age and burgeoning careers, allowed them to establish a strong foundation before committing to their future together.

2018: The Surprise Proposal in New Zealand

After a period of being "off," the couple reconciled and Josh Dun proposed to Debby Ryan in December 2018. The romantic proposal took place in a treehouse in New Zealand, overlooking a stunning landscape. Dun presented Ryan with a ring and a promise ring, signifying his commitment. The proposal was a major public step, confirming their serious intent to their global fanbase.

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The Secret New Year’s Eve Wedding That Shocked Fans

In a move that perfectly encapsulated their private nature, Josh Dun and Debby Ryan secretly married on New Year's Eve, December 31, 2019, in Austin, Texas. The news was kept completely private until May 2020, when a photo from the wedding appeared in a magazine, confirming the long-held fan speculation.

Planning a "Gatsby-Level Dance Party" in 28 Days

The wedding was anything but traditional, reflecting the couple's spontaneous and creative personalities. The entire event was reportedly planned in a whirlwind 28 days by event planner Alex Moreau of XO Moreau.

• The Venue: The ceremony and reception were held at the Hotel Van Zandt in Austin, Texas.
• The Vibe: Ryan described the desired theme as feeling "like game night at our place had [turned into] a Gatsby-level dance party."
• The Attire: Debby Ryan wore a breathtaking, custom-made lace gown by renowned designer Elie Saab, while Josh Dun opted for a luxurious velvet suit from Paul Smith.

The decision to marry on New Year's Eve added an extra layer of meaning, making their anniversary a celebration of both their commitment and the turning of a new year. The secrecy surrounding the event allowed them to enjoy an intimate, stress-free day focused purely on their union.

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The New Chapter: Welcoming Felix Winter Dun (2025 Update)

The most significant and recent update in the Josh Dun and Debby Ryan saga is their entry into parenthood, a highly anticipated event by their followers and the media. This news solidifies their transition from a celebrity couple to a young family.

The Pregnancy and Birth Announcement

On September 7, 2025, the couple announced they were expecting their first child together, sharing intimate photos of Debby Ryan's baby bump. The news dominated social media, with fans and fellow celebrities offering an outpouring of congratulations.

The excitement reached its peak in December 2025. On December 13, 2025, Debby Ryan and Josh Dun announced the birth of their first child, a baby girl named Felix Winter Dun. Ryan shared details of her emotional home birth on Instagram, giving fans a rare, personal glimpse into their private life. The name "Felix," meaning "lucky" or "successful," and "Winter," a nod to the season of her birth, holds a beautiful significance for the couple.

Topical Authority: The Intersection of Music and Film

The Dun-Ryan family represents a unique blend of the pop-rock music world and the Hollywood acting scene. Josh Dun's work with Twenty One Pilots, including their latest projects and tours, will now be balanced with the responsibilities of fatherhood. Similarly, Debby Ryan, known for her versatility across Disney and Netflix, is embracing her new role as a mother while continuing her career. Their ability to manage high-profile careers while maintaining a stable, loving family life serves as an inspiration to their millions of fans.

The birth of Felix Winter Dun marks a beautiful new beginning for the couple. Their relationship, built on a foundation of shared faith, mutual respect, and a commitment to privacy, has shown remarkable resilience and growth. As they embark on this new chapter of parenthood, fans are eagerly watching for more glimpses into the life of this captivating and deeply private celebrity family.