Inside Katy Perry's Dramatic Path to Forever With Orlando Bloom

Before Katy Perry could go "full bloom" with her now-fiancé Orlanda Bloom, she had to absorb some tough lessons about love.

By Sarah Grossbart Feb 14, 2020 2:30 PMTags
Watch: Katy Perry's Engagement Ring: Get All the Details

Just weeks before her Valentine's Day engagement last year, Katy Perry sat down with Paper magazine and admitted she wasn't so sure she had full faith in the institute of marriage. 

She had been there, tried that and, as most everyone knows, her 14-month marriage to Russell Brand has become more infamous for the callous way it ended than for any happiness it may have brought the "Part of Me" artist.

Back then, when she first connected with the comedian as he was hosting the 2009 MTV Video Music Awards, she "believed in Disney princesses" she told the outlet and the idea of being swept off into happily ever after. Now, though, "I'm very pragmatic and logistical and I am less fantastical about things. I mean, I was married when I was 25. I'm 34. It was almost 10 years ago. I was like, 'One person for the rest of my life,' and I'm not so sure that that idea is for me. I'm just such a different person than I was."

But when the man you love offers up a one-of-a-kind flower-shaped pink diamond during an elaborately planned mid-air proposal on February 14 of all days, well, that's hard to pass up. 

Besides, Perry and Orlando Bloom had already spent the previous few years putting themselves through the relationship wringer, making their choice as sensible as it is romantic. 

Taking a pause on their pairing in 2017—not a full break, really, as sources told E! News the British actor, 43, and the singer never ceased communication during the five-month hiatus—only served to show them just how much they valued their partnership. When they got back together that August (nothing says romantic date night like a motorcycle ride to an Ed Sheeran concert) they were determined to put any lingering issues to rest.

"Katy and Orlando want this to work this time, so they are working on mending their relationship," a source told E! News of the reconciliation. Her bond with Bloom's 9-year-old son Flynn was already rock solid and she got along great with his ex Miranda Kerr and her husband Evan Spiegel. All that was left for the couple was to strengthen their communication. Said the source, "They've had some really good talks and have a better understanding on their needs."

Katy Perry and Orlando Bloom's Road to Engagement

And Perry certainly has plenty of relationship experience to draw on. 

Back when she was best known as gospel singer Katy Hudson, she had her share of young, somewhat misguided teenage romance. She rocked out with Relient K frontman Matt Thiessen in the early aughts ("We're not too close, but yeah, she's a great person," he would tell years later) and split with troubled Sons of Anarchy actor Johnny Lewis in 2006, his untimely 2012 passing after he fell off a roof reportedly inspiring her somber single "The One That Got Away". 

And by the time she exploded onto the scene with 2008's racy for the times "I Kissed a Girl" she had already cemented her preferred make-out partner in Gym Class Heroes' Travie McCoy

Just two years away from his catchy Bruno Mars collaboration "Billionaire", the couple seemed primed for music power couple status. 

Chris Polk/FilmMagic

"We looked really cute together. We get along better than any other girl I've ever hung out with in my life. That was the beginning of a really really awesome time for me," he would later share on a 2012 VH1 Behind the Music special. "When I was around her I felt really at ease and comfortable with myself...It was the most amazing thing ever."

But as he struggled with prescription drug use, their union faltered. "She wasn't stupid....She knew when I was f--ked up," he shared. "I chose drugs over our relationship....As things started taking off for her the more I started to doubt my role in her life. There were times I felt like a stepping ladder."

And when she chose to break it off later that year, via email, he was left crushed. "It started off with 'I love you so much I hate to do this...'" he recalled. "Someone that you are ready to spend the rest of your life with sends you a f--king email just s--ting on your whole parade. It destroyed me."

Francois Durand/Getty Images

He responded by taking to his blog to confirm the split, borrowing lyrics from "Looking at the Front Door", Main Source's break-up anthem ("We fight every night, now that's not kosher / I reminisce with bliss of when we was closer / And wake up to be greeted by an argument again / You act like you're ten,"). And suddenly Perry's "Hot N Cold" made perfect sense. 

"When you breakup with someone you move on," Perry shared while performing an acoustic set at L.A.'s Hotel Cafe in January 2009. "You don't really want to move on…but you have to because they don't give you any choice. But I'm over it!"

Proving her vow to be true she danced around the idea of getting together with close pal Josh Groban ("We might have skated on the line of dating," he told Details) before going all in with Brand. 

Mere months after flirting their way through rehearsals for the 2009 VMAs, the Get Him to the Greek star proposed on New Year's Eve at a tiger sanctuary in Rajasthan, India during an elaborate December holiday. They would return to the spot 10 months later for a days-long wedding celebration featuring a Bollywood-themed party and a Christian ceremony at the Aman-i-Khas luxury resort.

Frank Micelotta/PictureGroup via AP IMAGES

By their one-year anniversary the couple were either splitting up or expecting their first child, depending on the day and the story you chose to read. Perry did little to dissuade the latter, telling Ellen DeGeneres, "I would love to have children. I think that's one of the reasons you get married, and especially to the person that you marry. You think, 'Hmmm, that person is going to be a good partner, a good parent.'" 

And with his own visit to The Ellen DeGeneres Show in December 2011, Brand denied there were issues, adding, "I've treated the whole Internet now like it's a wicked little liar. Yeah. I am really happily married. I'm married to Katy. Perpetually, until death do us part was the pledge."

Or, until the calendar turns, the twosome closing out the year separated. By February, Perry's hair was tinted blue and her mindset set to #overit, making a splash at the Grammys with a new single that quipped, in part, that he could keep the diamond ring. 

Having been in the works for a bit, "Part of Me" may have began as a message to McCoy but it's release couldn't have been a better timed dagger to Brand, the empowerment anthem delivering the ultimate F you to an ex she wouldn't look back on all that fondly. 


"He's a very smart man, and I was in love with him when I married him," the singer began her interview for the July 2013 issue of Vogue. "Let's just say I haven't heard from him since he texted me saying he was divorcing me December 31, 2011."

Well, then. 

Her powerhouse single also provided the title for her 2012 documentary, an entirely open look at her wildly successful California Dreams tour, which admittedly ate up the bulk of her marriage to Brand. 

Though she had made time to play spectator as well, catching her husband performing his standup act. In the beginning, she told Vogue, she found his decidedly crass brand of humor "hysterical," that is right up "until he started making jokes about me and he didn't know I was in the audience, because I had come to surprise him at one of his shows. So. Hysterical to a point. I mean, I have to claim my own responsibility in things. I do admit that I was on the road a lot." 

Katy Perry & Russell Brand: Romance Rewind

But even riding a peak of her career, she made all necessary attempts to prioritize her marriage. "I invited him time and time again, and I tried to come home as much as I possibly could. You saw that in the movie. That wasn't edited to leave footage out—there wasn't any footage of him."

Ultimately, she speculated, he wasn't ready to hitch his wagon to a confident, international pop star unafraid of speaking her mind. 

"At first when I met [Brand], he wanted an equal," she told Vogue, "and I think a lot of times strong men do want an equal, but then they get that equal and they're like, I can't handle the equalness. He didn't like the atmosphere of me being the boss on tour. So that was really hurtful, and it was very controlling, which was upsetting. I felt a lot of responsibility for it ending, but then I found out the real truth, which I can't necessarily disclose because I keep it locked in my safe for a rainy day." 

What she would share, however, was the end result. "I let go and I was like: This isn't because of me; this is beyond me. So I have moved on from that."

In other words, it's not me, it's definitely you.

Dome/Nathanael Jones,

By that point, following rumors of a romance with 22-year-old French model Baptiste Giabiconi and a dalliance with Florence + the Machine guitarist Robert Ackroyd she told USA Today was "not even appropriate to label", she'd already gone one round with John Mayer

Following their initial March 2013 breakup, she penned "Unconditionally," likely more well received than Taylor Swift's "Dear John" and anything Jessica Simpson might have dreamt up after their rollercoaster romance. 

"He pulled away. That was a big hello for me," she talked about the split with Elle U.K. "I realized I could lose the person I loved and I had to deal with some things, issues I think a lot of women have," she continued. "You can be strong in one aspect of your life but submissive in another. In relationships, it was hard for me to speak up and set boundaries. I think a lot of that was to do with the fear of loss."

ABC/Ida Mae Astute

But by the time she spoke to Vogue that summer, she already seemed ready to risk heartbreak again. "I still am madly in love with him," she said of Mayer. "All I can say about that relationship is that he's got a beautiful mind....Beautiful mind, tortured soul. I do have to figure out why I am attracted to these broken birds."

Along with releasing her fourth disc, Prism that year, featuring her ode to inner strength, "Roar", she recorded "Who You Love" with Mayer, a number that landed on his 2013 album Paradise Valley. 

Engagement speculation increased as Perry took to wearing suspicious-seeming baubles on her left hand, but they split again in February 2014 as she headed out on her Prismatic World Tour and enjoyed some decidedly cozy, but undefined outings with DJ-producer Diplo.

Then, as she was celebrating her largely successful Super Bowl halftime performance in 2015 that introduced the world to Left Shark, she reunited with Mayer once more. 

"I don't like to live in fear because that traps you and your voices. Fear is a control tactic in the world that is negative and depressing and I don't want to be associated with it," Perry reflected to Australia's Daily Telegraphin May 2015. "I'm excited by whatever it brings. I'm excited by own evolution."

Astrid Stawiarz/Getty Images

As far as having any trepidation about falling in love once more, she shared, "I'm excited by whatever it brings. I'm excited by my own evolution. I don't want to end up bittersweet. I have to evolve, I have to continue to push people's perceptions of me. As an artist I like to do that, keep people on the edge of their seats." 

So when she and Mayer called things off again in the summer of 2015, the natural assumption was that they were due for at least one more refrain. 

That is, until she and Bloom, he of the popular Lord of the Rings and Pirates of the Caribbean franchises, were spotted flirting their way through Netflix's Golden Globes after-party the next January. (Apparently their meet-cute involved Denzel Washington and an In-N-Out burger.) From there it was trips to Hawaii and London and an altogether successful introduction to Flynn. By May, Perry had made the romance Instagram official, sharing a photo of them sprawled out on a mansion staircase mid-Cannes film festival with the caption, "we cannes't."

Which is right around when friends started whispering that Bloom intended to propose to Perry "before the year is up." 

First, though, he'd play proud boyfriend, photographing the singer as she performed the on-theme "Roar" at the Democratic National Convention and even helping her write her speech.

The pair appeared to be such a strong team—and their romance an idyllic whir of globe-hopping, featuring trips to Sardinia, Tokyo and Palm Springs, where she feted him with a surprise 40th birthday bash—that the news in early 2017 they'd decided to take "respectful, loving space," after little more than a year together was awfully sad. 

"Katy pulled the plug," an insider told E! News. "It was a few events that happened over the past few months. They both still love each other very much, though, and getting back together could happen once they have some space."

As is apt to occur, fans were quick to assign blame, with one People headline blaring "Orlando Bloom Had One Foot Out the Door With Katy Perry." But Perry was quick to bat down the idea that anyone should be at fault. "How bout a new way of thinking for 2017," she tweeted. "U can still b friends & love ur former partners! No one's a victim or a villain, get a life y'all!"


A quite prescient move considering they would be full speed ahead by August. 

Though the pair knew it would be tough rebuilding their union amid Perry's worldwide Witness tour, they proved to be up for the challenge, squeezing in visits to the Maldives, a March trip to Tokyo that saw them dressing as Mario and Luigi for a go-kart date and an April stop at the Vatican to meet Pope Francis with Perry's mom. And, finally, in September 2018, the pair walked their first joint red carpet at the Gala for the Global Ocean, hosted by Prince Albert II of Monaco, at the Opera of Monte-Carlo.

"Katy has never been happier and everyone around thinks that Orlando is great for her," a source told E! News shortly after. "Katy can really be herself, with no judgment."

But she didn't dare dream about what might come next. "They have discussed getting engaged but Katy did not think it was going to happen so soon," a source tells E! News. 

David Fisher/Shutterstock

Or quite so spectacularly. To mark what has become their favorite shared holiday, a source tells E! News, he proposed after their private Valentine's Day dinner celebration. He'd booked a helicopter, bought a bottle of champs and, of course, designed the floral-inspired ring based on the hints Perry had dropped. 

Then, as he handed her the note he'd written expressing her feelings, things began to go hilariously awry. "The champagne is, like, broken. The bottle is everywhere, and I'm still looking at the note," she recalled on Jimmy Kimmel Live! weeks later. "He's pulling out this box that's too big for his coat pocket. It rips his coat pocket, and his elbow goes into the champagne."

Even so, she continued, "He did so well."

Better still when she realized that their helicopter hadn't landed on a random rooftop but at a private penthouse in downtown L.A.  filled with red roses, her parents and some 30 of their closest friends. 

Katy Perry & Orlando Bloom's Cutest Moments

Sworn to secrecy, her friends donned red sweatshirts emblazoned with the phrase "OK" and "everyone in the room cheered for them as they walked in and they had a champagne toast," says the source. Wiping away tears of happiness, Perry continued to marvel at her good fortune.

"Katy is over the moon and so excited. She has always said that Orlando's love for her was different than anything she has felt before," says the source. 

Because she's put in the work, learned what she needs and when she and the actor wed later this year, she feels totally confident that they're ready to commit to forever. "I've gone to therapy, been through the Hoffman Process, done plant medicine...And I have a partner who is also all about finding a balance—Orlando, who is on a spiritual journey of his own. He's an anchor who holds me down, and he's very real," she told Vogue India last month. "Love is different from dating. You date in your twenties. Love is partnership, friendship, truth and being an absolute mirror to someone." 

(Originally published Feb. 16, 2019 at 3:00 a.m. PT)

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