In those three years following that fateful Golden Globes after party in 2016 where the the “Chained to the Rhythm” singer first crossed paths with the Pirates of the Caribbean actor, who turns 42 on Sunday, Jan. 13, the couple have been through it. From break ups to make ups, nude photo scandals and blending families, Katy and Orlando have managed to keep their romance as private as possible, perhaps the lesson learned from the failed marriages in both stars’ recent pasts.
Whatever the reason, they’ve managed to keep their relationship something that, through the good and the bad, is truly theirs. And to think, for a while there, it didn’t seem like we’d get back to this place.
Weeks after the Golden Globes, they took in an LA performance of the play The Absolute Brightness of Leonard Pelkey, popping up in a photo on the playwright’s Instagram, though still maintaining a bit of distance between one another. Then there was a February Adele concert and trip to Hawaii, followed by March’s trips to London and Santa Barbara, where it became clear that these two were more than just friends.
“Katy likes how down to earth Orlando is,” a source told E! News that month. “They seem to be getting serious and are an official couple. She calls him her boyfriend.”
By then, Katy had already met Flynn, Orlando’s young son with ex-wife Miranda Kerr. “Katy has met Flynn, and they get along wonderful,” a source told us that February. “She thinks he is so cute and such a well behaved kid! Katy would [also] like kids one day, and she is vocal about that.”
So, you could say that things were moving ahead at full steam. However, despite all their continued couple-y sightings throughout that spring, the pair were hesitant to publicly acknowledge exactly what was going on between then, especially where it mattered most: social media. Until, that is, the Instagram post that changed everything in May.
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As spring gave way to summer, a source told E! News that things were getting more serious between the two than anyone had even imagined. “They are in love and happier than ever. [Orlando] would like to get engaged to [Katy] before the year is up,” the insider said.
By July, Orlando was performing the role of proud boyfriend as Katy took the stage at the Democratic National Convention, snapping a pic of her on his iPhone from the stands as she spoke and performed her hit track “Roar.” Days later, Katy would reveal on Twitter that “Lando” even helped her out with her speech.
A month later, they would take their steamy romance overseas yet again for a trip to Sardinia in southern Italy. “Katy and Orlando enjoy traveling together, so whenever they have an opportunity they try to make it work,” a source told E! News. “All of Katy’s friends and family like Orlando, so bringing him away with her is always a great time.”
But while there, they’d get caught up in their first bit of international scandal when, while enjoying an afternoon of paddleboarding, Orlando stripped down to his birthday suit and was photographed by an incredibly intrusive paparazzo. In the immediate aftermath, he would joke about the incident on Instagram, with a video of him running in slow-motion captioned, “when you are chasing down the guy who stole your swimming trunks.”
But the following April, he’d open up to Elle U.K. about the shock of being caught in such an intimate moment. “I wouldn’t have put myself in that position if I’d thought it would happen. I’ve been photographed a million times in a million different ways. I have a good radar. We’d been completely alone for five days—nothing around us. There was no way anyone could get anything,” he recalled. “I had a moment of feeling free. What can I tell you? Note to self: You’re never free. Ha!”
Despite the rumors, the couple spent Thanksgiving together and embarked on another of their beloved trips to ring in 2017 with a visit to Tokyo. And with Orlando’s birthday falling right around the time they met, Katy helped celebrate a year of knowing her beau with a kick-ass surprise 40th birthday bash in Palm Springs, Calif., where guests received onesies covered with photos of his face.
And yet, one month later and just a day after posing together for a photo inside Vanity Fair‘s Oscar after party (where they did not walk the red carpet together), they were confirming that they’d broken up. In a joint statement released to E! News, their reps shared, “Before rumors or falsifications get out of hand we can confirm that Orlando and Katy are taking respectful, loving space at this time.”
While no one really knew what went wrong between the lovebirds, Katy was quick to explain on Twitter that no one was to blame for the breakup. “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!”
And Orlando told Elle U.K. that the split was a decidedly friendly one. “We’re friends. It’s good. We’re all grown-up,” he told the publication. “She happens to be someone who is very visible, but I don’t think anybody cares about what I’m up to. Nor should they. It’s between us. It’s better to set an example for kids and show that [breakups] don’t have to be about hate.”
And he wasn’t kidding.
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“They looked like they were having the time of their lives,” the insider continued. “People didn’t really bug her. I don’t really think people knew it was them because they had hats on and stuff.”
Rumors of a reconciliation only intensified at the turn of the year when the two were spotted together while on holiday in the Maldives. “Katy was in Dubai and then stopped over in Maldives where she met up with Orlando,” a source told us at the time. “It’s a few hours away and Katy wanted to stop there since it was pretty close.”
However, no one involved was ready to say that this relationship was all the way back on. “Katy and Orlando have never lost touch and it’s nothing serious,” one insider told us. “They keep in contact frequently and Orlando is understanding of her crazy schedule right now. It’s pretty casual between the two.” According to another, “They have not lost contact. They are just keeping their close connection on the low lately. They speak all the time.”
By March, Katy was back to leaving cheeky comments on Orlando’s Instagram and, in April, she essentially confirmed what we all knew during an interview with Entertainment Tonight when she was asked if she’d ever date a contestant on her new gig as head judge of ABC’s American Idol revival.
“No, I’m sorry I have been spoken for and speak for myself,” she said, adding, “And I’m very happy!”
The reporter responded, “You’re spoken for right now?!” and Katy replied, “Yeah, girl, of course I am!”
But it wasn’t until September 26 when, for the first time since meeting one another in 2016, the pair walked together on the red (well, technically, grey) carpet at the Gala for the Global Ocean, hosted by Prince Albert II of Monaco, at the Opera of Monte-Carlo. From then on, it was abundantly clear that this relationship was fully back in the “on” position.
A month later, as Orlando helped Katy celebrate her 34th birthday, we learned just how back on as photogs spotted the couple with Flynn as Miranda picked him up. As Katy gave the youngster a hug goodbye, his mom showered her ex-husband’s new lady with gifts.
And as we learned then, it was only a matter of time before she and Orlando took the next step in their rekindled relationship. “Katy and Orlando want to get engaged very soon,” the insider continued. “They have talked about it a lot and she is hoping it will come soon. Their time apart made them realize they want to be together.”
While there’s been no public sign of an engagement just yet, Katy and Orlando spent the rest of 2018 being super loved-up, with Katy paying $50,000 for a date with her beau during a charity auction at the One Love Malibu benefit show in December, in support of those affected by the Woolsey wildfire, before they embarked on yet another Hawaiian getaway, spending time with Flynn and Orlando’s mom.
An insider told E! News that they had a “great trip and are very in love.”
“Katy was wonderful with Flynn and seems very close to Orlando’s family,” they added. “They all got along great.”
As Orlando prepared to celebrate his 42nd birthday, he took to Instagram to share some musings with his fans. “i’m grateful and as I contemplate the passage of time I really feel age is just a number and we are not…we ARE the choices we make, the words we speak, the thoughts we create and the actions we take…they shape our realities…and as I say to myself and my son…make smart choices,” he wrote.
And right there in the comments? His lady, Katy.
“Glad I made the right choice doe,” she wrote in a since-deleted comment. “Happy birthday angel.”