Even at a young age, some Hollywood celebrities tend to have a long list of boyfriends. Debby Ryan is definitely one such actress who at a mere age of 25 is already a veteran in this aspect. She has dated numerous fellow actors you could almost run out of fingers while counting.

As for right now, Ryan is currently taken. In fact, she is dating someone with whom she has stayed longest compared to all her past affairs.

Debby Ryan Currently Dating Josh Dun

Debby Ryan is currently in a relationship with Twenty One Pilots drummer named Josh Dun. However, the road was not always smooth sailing for the pair as they encountered some bumps along the way.

The couple never really confirmed their relationship in interviews, but Josh's Instagram suggested the lovebirds began dating in 2013.

Debby Ryan with her boyfriend Josh Dun
Source: Pop Buzz

It was reported Josh took Ryan to a candlelit dinner in a treehouse around Valentine's Day 2014. Moreover, when he went on a tour with his band Twenty One Pilots, he mailed a care package with a kind letter.

Furthermore, it was sweet of Ryan to mail his pink sweatshirt too - that apparently she always tried to steal, just to show how much he missed Ryan.

The couple seemed absolutely perfect together. However, after dating for a year, Josh confirmed via social media that the two broke up and seemingly went separate ways in 2014.

In March 2015, Debby talked about abusive relationships. Speaking to Teen Vogue, the actress said:

"People that demand your password and always look over your shoulder, ask who you’re texting, and grab your phone and let themselves in — that’s not okay."

This made people wonder if she was talking about her former boyfriend Josh. However, she revealed that the person was, in fact, one of her friends.

Moreover, Ryan shared, Josh was a perfect boyfriend for her before things went south in their relationship. After ending their relationship in friendly terms, the couple was not seen together for a couple of years.

Debby Ryan once broke up with Josh Dun before getting back together
Source: J-14

In 2016, the two were spotted again at a Christmas Party which was thrown by John Feldman, a music producer. The former couple was spotted posing for a picture together which created speculations if they had gotten back together.

Although there are no concrete reports on their dating endeavors since then, the pair's social media seems to provide evidence of their togetherness. The couple appears very much in love and they could take the next giant leap in their relationship soon.

Debby Ryan's Past Affairs

Debby Ryan appears to have a long list of past affairs. Some were rumors, while the others were confirmed reports.

In 2013, Ryan was rumored to be dating a co-star named Spencer Boldman. After Spencer's brief guest role on the TV series Jessie where Debby played the lead role, things started heating up. However, Spencer later speaking of Debby said he loves that girl but they're just friends.

Debby Ryan and Spencer Boldman
Source: Just Jared

In June 2010 during an M Magazine photoshoot, Debby's phone was apparently blowing up with texts from actor James Franco who reportedly had a crush on her.

Franco was striving to take their friendship to the next level but it looks like nothing really happened except a few flirty banters. Any romantic potential between the pair soon fizzled out.

Back in late 2010, Debby was linked to a Hollywood actor Lucas Till. The pair was reportedly together for only a few months before they ended things.

Earlier in the same year, Debby was romantically linked with a fellow Disney channel member Gregg Sulkin. Although they denied the rumors of them being a couple, they continued to appear together in events.

Debby Ryan and Gregg Sulkin
Source: Zimbio

The last time the pair was seen together was in 2012 and it was never revealed what happened between the duo.

In 2009, Debby was in a rumored relationship with Sean Marquette, although it was reportedly brief. The couple preferred to be tight-lipped about their affairs, so it was not sure when they ended things.

Earlier in 2008, the actress was in a romantic relationship with a fellow co-star of Good Luck Charlie named Jason Dolley.

Debby Ryan and Jason Dolley
Source: Deposit Photos

However, the couple was not meant to be as they called it quits merely a year later in 2009.

Debby Ryan: Quick Facts


Source: Teen Vogue
  • Born on 13th May 1993 in Huntsville, Alabama.
  • Her birth sign is Taurus.
  • Her parents are Missy Ryan and John Ryan.
  • She has an older brother named Chase Ryan.
  • Her father was in the military, so she moved to various homes in America and Europe during her childhood.
  • She lived in Germany until she was 10.
  • She can speak both English and German.
  • She began performing in theatres when she was 7 on an American base in Germany.
  • She returned to the US in 2003 where she was raised in Texas.
  • She referred to herself as a "nerd" in an interview.
  • She was bullied in middle school.
  • She was a member of the school's chess club.
  • She is best known for featuring in the series The Suite Life On Deck and Jessie.
  • She starred in the TV movie 16 Wishes which became the most watched cable program.
  • She starred as Tara Adams in the Disney film Radio Rebel.
  • She starred alongside Brenda Song in The Suite Life on Deck.
  • In 2018, she began portraying Patty in Netflix series Insatiable.
  • Her net worth is estimated to be $4 million.