Debby Ryan Dating Timeline, Relationship History, Past Boyfriends

It’s been a while since former Disney Channel star Debby Ryan made headlines, but recently, she found herself in hot water when Netflix dropped the trailer for her upcoming series, Insatiable. Immediately upon seeing the preview for the show, people were livid. Why? Because the series seems to be centered around an overweight girl’s journey from being bullied to being loved and accepted once she sheds some weight, which is problematic for many reasons.

Despite the backlash that Debby (and Netflix) has received since the trailer came out, it actually got us thinking: What is Debby up to these days? Is she working on any other projects besides Insatiable? Is she traveling the world? Is she dating anyone new? And, while we’re at it, which stars has she even dated in the past? If you need a refresher, take a look at these nine hotties Debby’s been linked to throughout her career:

Jason Dolley

Although Jason Dolley and Debby never flat out confirmed their relationship, fans were pretty certain that there was something going on between the Good Luck Charlie co-stars back in 2008. TBH, lots of celebs wind up dating people that they met on set, so it makes total sense, but even if they did date, it turned out that they simply weren’t meant to be.

That’s right, y’all! In 2009, Debby was also linked to a couple of other guys in Hollywood, so clearly, whatever was going with Jason didn’t last. Still, we’d love to know if the two were just hooking up at the time or if they were actually in an exclusive relationship, but honestly, if we haven’t found out the truth by now, we never will.

Sean Marquette

We’ll be real with you… very little is known about Debby’s former relationship with Sean Marquette other than the fact that the two briefly dated in 2009. Even though the couple remained tight-lipped about their relationship, we have to be honest… we totally respect it!

Normally, it’s super hard for celebs to keep their private lives private, and at the time, Debby was very well-known on Disney Channel, so the fact that they kept their short romance under wraps is actually super impressive. Don’t you think?

Gregg Sulkin

After they hit the red carpet together at the beginning of 2010, rumors began swirling that Debby and fellow Disney Channel member Gregg Sulkin were a couple. The pair both denied that they were anything more than friends, but they continued to hit the town together despite the rumors that were swirling at the time. The last time Grebby was seen together was in early 2012, but we’re still not 100 percent positive what actually happened between them. Hmm…

Lucas Till

Shortly after the Gregg Sulkin dating rumors began to die down, Debby was linked to another Hollywood hottie: Lucas Till! The pair reportedly saw each other for only a few months before they ended things, so clearly, they weren’t compatible. Still, their short-lived romance is worth mentioning (even though it didn’t even last a total of five months).

Jean-Luc Bilodeau

According to J-14, even though the 16 Wishes co-stars never admitted to dating IRL, Deb and Jean-Luc Bilodeau spent some time getting cozy after the movie stopped filming. As we mentioned earlier, dating after meeting on set is totally normal, so this isn’t at all surprisingly, but if anything, we think these two were probably just hooking up and never actually entered into a full-on relaysh. What do you think?

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James Maslow

While at an M magazine photoshoot in June 2010, Debby’s phone was apparently blowing up with texts from the Big Time Rush crooner, which can only mean one thing… right? It was from there that reports surfaced that James Franco had a major crush on Debby and was trying to take their friendship to the next level.

In hindsight, this doesn’t sound like it was anything more than some flirty banter, but NGL, if they were in a full-blown relationship, we probably would’ve shipped it! Thoughts?

Cole Sprouse

Even before Bailey and Cody got together on The Suite Life on Deck, Debby and Cole Sprouse faced constant dating rumors. If you were a fan of the series, the truth of the matter is, you probably shipped these two on screen and off screen, but sadly, they never actually dated IRL.

Unlike their Disney Channel characters, the two only ended up being friends. We know… what a bummer! But hey, we’d be friends with Cole Sprouse too if we had the chance, so we can’t really blame her!

Spencer Boldman

Again with the co-star dating rumors! Following a brief guest-starring stint on Jessie back in 2013, people began wondering what the status of Spencer Boldman and Debby’s relationship really was. Just last month, the actor cleared the air saying that he “love[s] that girl,” but that they’re just friends. Even though they didn’t date, we have to admit, his comment was super sweet, so at the very least, we’re glad to see that they’re good friends.

Josh Dun

NGL, Debby and the Twenty One Pilots drummer seemed absolutely perfect together, but after dating for over a year, Josh Dun confirmed via Instagram that the two broke up. The good news is, Debby and Josh rekindled their romance back in 2016 and are still dating to this day. GOALS!

Although we don’t know much about their relationship, the two appear to be very much in love on Instagram, and since they started dating way back in 2013, we’d venture to guess that, at this point, things are very serious between the two. Congrats, guys!

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