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Crushing on The ‘Wicked ‘ly Charming Jonathan Bailey? Same. Here’s Who He Has Dated

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Jonathan Bailey has me in a chokehold, and honestly, it’s not my fault he’s that charming.

One thing that’s fully living rent-free in my brain is that mirror selfie Ariana Grande dropped with her, Cynthia Erivo, and Jonathan Bailey. Can we just pause for a second to talk about Jonathan in this pic? 

The way he’s staring directly into the camera—giving smolder, confidence, and maybe a sprinkle of “I know I’m your new crush”—has me absolutely losing it.

He looks so good that I might need someone to call an ambulance because, oh no… I think I just fell in love. 

The Wicked trio is already iconic, but Jonathan in that moment? He’s the main character, and we’re all just extras. Help. Please.

Okay, so let’s talk about the absolute obsession I’ve developed for Jonathan Bailey. It all started back in Bridgerton season 2, where he had me swooning as the brooding and oh-so-dramatic Anthony Bridgerton. 

And don’t even get me started on the insane chemistry between him and Simone Ashley—seriously, they had me screaming into my pillow. 

But now? Now, he’s gone and leveled up because his performance as Fiyero in Wicked has me fully convinced I’m experiencing something deeper. 

The ‘Wicked’ main characters/Instagram 

Like, could this be true love? Because of the way he flirts, flips, and dances his way through Oz? Simply unmatched.

If I were a student at Shiz University, best believe my major would just be “Chasing Fiyero 101.” It’s giving delulu, but can you blame me? 

Jonathan Bailey is out here stealing hearts, and I am in the front row, no intermission. The man was born to play Oz’s certified heartthrob, TheyGossip.com reports. 

Meanwhile, we’ve got Cynthia Erivo soaring through “Defying Gravity” (literally) and Ariana Grande serving high-kicks, sass, and giggles as Glinda. This cast is iconic—don’t walk, RUN to get your tickets to Wicked ASAP.

But let’s circle back to Jonathan because, as I left the theater, I was hit with this devastating realization: Jonathan and I are not dating. Tragic, right? 

Naturally, I did what any self-respecting fan would do and went full detective mode to learn about his love life. 

So, who has Jonathan Bailey dated? Is there a lucky someone currently holding his heart? Let’s break it all down, because yes, I’m sharing Jonathan’s full dating history, and you’re so welcome for this deep dive.

Who Has Jonathan Bailey Dated?

When it comes to heartthrobs, Jonathan Bailey is the moment. But while most of us were busy crushing on him as Anthony Bridgerton or swooning over his dance moves as Fiyero in Wicked, Jonathan’s actual love life has been playing out quietly behind the scenes. 

Unlike his swoony on-screen characters, Jonathan keeps things pretty low-key IRL. Still, we’ve managed to gather some juicy deets about his dating history, and yes, we’re sharing everything. Let’s get into it.

Jonathan Bailey and James Ellis 

If you need a minute to process the cuteness, take it, because JOnathan’s rumored romance with James Ellis was next-level adorable.  

James and Jonathan/Getty

Back in 2019, whispers about the two dating started circulating, and those rumors were basically confirmed at the Olivier Awards that year. 

When Jonathan snagged the award for his role in the West End musical Company, he kissed James before heading to the stage, and honestly? Our hearts melted. 

During his acceptance speech, Jonathan got real about LGBTQ+ representation, saying:

“At a time where acknowledging the very existence of LGBTQ people in our schools is being questioned, we have been able to, as a company, show a lovely and celebratory snapshot of gay love. LGBTQ people really aren’t that different. We’re just as anxious, and we’re just as flawed and desperate to fall in love as everyone else.”

He dedicated his award to the cast of Company, making it a moment that was as touching as it was iconic.

Jonathan’s Current Dating Life 

Fast-forward to December 2023, and Jonathan dropped a little update about his relationship status. 

In an interview with The Evening Standard, he shared that he was seeing a “lovely man” but didn’t spill much more. His reason? Privacy is a major priority.

The one and only Jonathan Bailey

“It’s not secret, but it’s private,” Jonathan explained. “Having a private life is, for me, completely critical. I don’t know if I would be able to be as confident to speak out on other things if I felt that my whole life was up for grabs.”

And you know what? We respect it. Protect your peace, King!

Why We Are All Obsessed?

Jonathan Bailey isn’t just a dreamy actor; he’s also using his platform to speak out on important issues, all while keeping his personal life on his terms. 

Whether he’s passionately advocating for LGBTQ+ representation or keeping us glued to our screens with his iconic performances, Jonathan continues to prove he’s a star both on and off the stage.

So, while the details of his love life might be hush-hush, one thing’s clear: Jonathan Bailey is absolute boyfriend goals, and yes, we’re all a little bit in love with him.

Elsa Gecaj
Elsa Gecaj
Elsa is a Gossip Columnist at TheyGossip news. She holds a Master's Degree in Journalism and Mass Communication from the University of Pristina, specializing in investigative journalism, and fact-checking. She’s a reporter who enjoys covering about intimate relationship, celebrity news, and entertainment news. Besides her passion for journalism, she enjoys practicing yoga, singing along to her favorite songs, and painting landscapes. contact: elsa-gecaj@theygossip.com

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