From Heartbreak to Baby: The Romantic History That Katy Perry Has Unpacked in Her Most Personal Songs

From the wistful breakup tunes and empowerment anthems to her pregnancy reveal in her "Never Wore White" video, Katy Perry loves to deliver the news in song

By Natalie Finn Mar 05, 2020 5:20 PMTags

Katy Perry really delivered with her latest song.

Not only is her new single, "Never Worn White," a tribute to finding lasting love again with Orlando Bloom—"you took my armor off, and did it delicately, and I let my guard down, to show you what's underneath"—but she unmistakably caresses her baby bump in the video that dropped Wednesday night, her way of announcing that she's pregnant with her first child.

Theatrical, yes, but of course Perry shared the news with the world, including her countless devoted fans, in that fashion.

While her earlier career was peppered with deeply personal songs about heartbreak and toxic relationships in addition to the infectious confections like "Teenage Dream," as well as major empowerment anthems like "Roar," Perry's personal life has taken a till-forever turn—and so has her music. 

Katy Perry & Orlando Bloom's Cutest Moments

The title of her 2019 hit "Never Really Over" was basically the theme of her relationship with Bloom, which they put on hold in 2017, only to reunite a few months later and get engaged on Valentine's Day last year.

A source told E! News that they were aiming to get married in 2020, but no word yet on whether the baby news will speed up or prolong the process. This is the first child for Perry and second for Bloom, who's also dad to son Flynn with ex-wife Miranda Kerr.

"There's a lot that will be happening this summer," Perry promised on Instagram Live on Wednesday night after her video came out. "Not only will I be giving birth, literally, but also figuratively to something you guys have been waiting for. So let's just call it a double whammy. It's a two-for."

That certainly sounds as if the stork is also going to have a new album in his basket...


Perry, who lately has been balancing making music with being a judge on American Idol, has only released a few singles since her 2017 album Witness—which boasted the politically tinged "Chained to the Rhythm," the temporarily feud-prolonging "Swish Swish," and lovers' laments such as "Save as Draft," "Déjà Vu" and "Miss You More."

Even the empowering tunes like "Hey Hey Hey" and "Pendulum" didn't feel that far removed from the breakup songs. But doesn't the end of a relationship tend to lead to those moments of enlightenment?

Perry's delightful announcement can't help but make a person think of the not easy road that she—or most people, really—traveled to get to where she wanted to be, in love and life, so much of which she chronicled in some fierce ballads and bangers along the way.

We don't claim to know for sure who caused the most pain or confusion or which hurt lingers the most, but since there's no such thing as art not reflecting life at least a little bit...the answers to the questions you may have about her most personal-sounding songs are in the pages of Perry's romantic history:

Matt Thiessen

Video of Perry rocking out and stage diving at a Relient K show in the early '00s—when she dated the band's frontman—made the rounds about 10 years later.

Thiessen mentioned Katy Perry in an interview with in 2012 and the interviewer seemed taken back, asking, "You're a friend of Katy Perry's?"

"I used to date her back in the day for a couple of years. But we're still really good friends," Thiessen said. He added, "We're not too close, but yeah, she's a great person."

Johnny Lewis

Perry was barely 21 when she started dating the troubled actor—who would go on to star in Sons of Anarchy but whose life was simultaneously unraveling. Lewis died in a freak occurrence in 2012, either falling off or jumping off the roof of the home where he'd been renting a room after beating his 81-year-old landlady to death.

"It wasn't a secret that Johnny had issues he was dealing with," a source who worked on SOA told E! News at the time. "No one could have expected it would end so tragically, though. Everyone is in shock."

Though everyone would assume in the moment that 2010's "Circle the Drain" was about Travis McCoy, after Lewis died a source told Us Weekly that Perry's relationship with the actor also played into the song, which is about only being able to stick around to watch and try to help for so long if the one you love is intent on destroying himself.

"He was in trouble then and she couldn't help him," the source said. "A lot of her songs were partially inspired by him. I know 'The One That Got Away' and 'Circle the Drain' are partly about him, as well as Travis. But she was young and it was a time in her life she cherishes...They had good times. It's really sad. She could never help him and couldn't [let herself] go in that direction."


Well, Perry certainly met the "Grace Kelly" singer, but their night hanging out at the Serpentine Gallery's summer party in London in 2008 (and then leaving together) never seemed to turn into anything.

Travis "Travie" McCoy

When Perry first burst onto the scene with "I Kissed a Girl" in 2008 she had been dating the Gym Class Heroes singer for over a year after appearing in the band's "Cupid's Chokehold" video, but they split up that December. McCoy, who had spent time in rehab that year for prescription drug addiction, announced the news on his blog on New Year's Eve with lyrics borrowed from Main Source's "Kickin at the Front Door"—all about a volatile relationship that's great when the couple isn't arguing, which is never. (So, "Hot n Cold"...)

"When you break up with someone, you move on," Perry reportedly told an audience at the Hotel Cafe during an intimate performance a couple weeks later. "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!"

When "Circle the Drain" leaked before Teenage Dream came out in 2010, everyone assumed it was about McCoy, about which he told MTV News: "I heard she put out a song that's about me, or about some old habits or whatever...I look at it like this: I'm just stoked that she finally has a song with some substance on her record. Good job."

But apparently time heals some wounds, because McCoy reportedly told London's Mirror in 2012 after Perry's divorce that she was "there for me through my hard times when things were really bad. Life goes on. I have regrets about the way we ended. But there are no grudges any more between us. I'll always be there for her, she knows that."

Benji Madden

After they partied together on Valentine's Day night in 2009, word got around that the newly single Perry was dating the Good Charlotte rocker.

"oh kittens!" she blogged about the rumors. "It's two pseudo famous people sitting next to each other...doesn't mean we were bumping uglies!"

Josh Groban

Not long after, Perry "might have skated on the line of dating" with the "You Raise Me Up" singer. (That's according to Groban himself in 2013.)

James Valentine

Sometime before she got married, Perry dated the Maroon 5 guitarist—according to Truth & Salvage Co. frontman Tim Jones. Talking to Blast Magazine in 2010, Jones revealed that Perry helped write the lyrics for his band's song "Old Piano," off of their self-titled 2010 LP. 

"She was dating my friend, James Valentine, who plays guitar in Maroon 5," Jones said. "We were up at his house one night, and she was asleep. He had a piano there, and it was late. I started playing and working on a song." At some point, she rolled over, asked what they were up to, sang a few words back to him, and went back to sleep.

Russell Brand

As we all know now, that turned out terribly. The garrulous comedian proposed while they were on holiday in India just a few months after meeting Perry in 2009. They returned to India to marry on Oct. 23, 2010, in a traditional Hindu ceremony in the middle of a tiger park, no bourgeois rituals for them. By December 2011, Brand had informed Perry via text that he wanted a divorce. Perry shared vulnerable moments in midst of their split in the concert documentary Katy Perry: Part of Me, and in 2013 Prism songs "Ghost" and "By the Grace of God" detailed the pain.

Meanwhile, Perry's performance of "Part of Me" at the 2012 Grammys was akin to the artist rising from the ashes, and "Wide Awake," about being jolted back to reality after being blinded by romantic promise, couldn't have been a timelier song when it dropped that May, either.

Baptiste Giabiconi

Perry kept company with the then 22-year-old French model in the wake of her divorce, spending time with him in Europe in March 2012. And who wouldn't have, friends or more?!

Robert Ackroyd

The Florence + the Machine guitarist was the object of Katy's affection at Coachella in April 2012 as she proceeded to sow her neglected oats following her divorce. She told USA Today that summer that she wasn't looking for a relationship anytime soon, saying her dalliance with Ackroyd was "not even appropriate to label. There are times I go out and meet people and flirt, but it's not really appropriate to have anything serious."

Moreover, "I have a second chance on life. To get maybe a better situation. For me, right now, I'm totally not looking. I'm just looking to heal. And I'm on that path. I'm not down on love."

John Mayer

No, she was not down on love! Instead, Perry fell hard and fast for the singer-songwriter (who had previously inspired Taylor Swift's "Dear John") and they embarked on a roller coaster relationship that didn't stop and start again once or twice, but multiple times over the course of four years.

After their March 2013 breakup she wrote "Unconditionally." 

"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 continues. "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."

Then, when GQ caught up with her at the end of 2013, they were together again and Perry was "having a wonderful experience with a wonderful guy. There's no rush."

Robert Pattinson

The longtime pals, via mutual friend Kristen Stewart, were rumored to be dating at one point after she and Mayer first broke up in March 2013—but as you can see, all is still just friendly between KP and RPattz (and his fiancée FKA twigs).

"I sent [Kristen] a text message saying, 'I know you've seen all this stuff, but you know I would never disrespect you. I'm not that person,'" Katy told Elle UK. "'I'm just trying to be a friend to him but it is unfortunate that I do have a set of tits."'

Jared Leto

Well, who hasn't been linked to the Oscar winner with the luscious locks? After she and Mayer broke up in 2014, both Perry and Leto were at Coachella and he was rumored to have been angling for a date, or at least more face time, with the pop star.


Neither Perry nor the DJ-producer (real name Thomas Wesley Pentz) ever confirmed they were more than friends, but they spent a lot of cozy-looking time together in 2014 after she and Mayer had broken up again. Either way, they were close enough for Diplo to raise a lot of Swifty hackles with a tweet about Taylor Swift's lack of a booty.

He and Taylor seemingly buried the hatchet a few months later at the Grammys.

John Mayer

This guy just kept popping up, until they finally seemed to part ways for good in 2015.

There was speculation that several tunes on 2017's Witness, including the title track and "Miss You More," boasted a little Mayer inspiration. That might have seemed after-the-fact, but 2013's Prism, which obviously addressed her old marriage ghosts, still crackled with pain, defiance and empowerment almost two years later. 

Besides, Mayer had just released "Still Feel Like Your Man," which he acknowledged was inspired by Perry, that April, so there's no statute of limitations on memories.

Orlando Bloom

These two hit it off at a 2016 Golden Globes after party and took it from there, traveling to Hawaii, Italy, the Democratic National Convention in Philadelphia and more.

The hot-and-heavy relationship seemed to have run its course, however, by early 2017. Their reps explained the split as the two taking "respectful, loving space" from each other—which indeed is far better than antagonistic, empty dumping via text.

"Katy pulled the plug," a source explained to E! News afterward. "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."

Consider the reboot of their relationship a success. "Full bloom," Perry captioned the photo of her engagement ring in 2019.

And now they're having a baby!

"I would love to have children," Perry said on The Ellen DeGeneres Show all the way back in 2011. "I think that's one of the reasons you get married. Especially to the person that you marry. You think, that person is going to be a good partner, a good parent."

Whether the baby or the vows come first, she's found the guy who made her premonition come true. And with that, Katy Perry's love story continues.

(Originally published June 9, 2017, at 5 a.m. PT)