Looking For Fireworks: Katy Perry's Dating History

Katy Perry may have kissed a girl and liked it, but she seems to enjoy kissing boys a lot more. Her dating history reads like a who’s who of 21^st century hipsters. She went from John Mayer to Russell Brand to finally settling down with Orlando Bloom.

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So who has Perry been with and what were the secrets and rumors that went on behind-the-scenes and under the covers? Is there any truth to the rumor that she dated Robert Pattinson? Just how did Brand end their brief but whirlwind of a marriage? And how did she end up engaged to Bloom?

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Take a stroll down the unusual and winding path that love has created for Perry and discover why she feels the need to Roar now and then.

Perry’s first boyfriend was none other than Justin York back in 2002. According to FamousFix, Perry admitted on Twitter that she lost her virginity to him. And she told Howard Stern that it was quick, unpleasant and in front of a Nashville construction site. York, if you haven’t heard of him, is a singer-guitarist who sometimes performs with Paramore.

Matt Thiessen, the singer with Christian rock group Relient K, was her next boyfriend. According to NewReleaseToday, Perry would sometimes join him on stage — even stage diving. Thiessen returned the favor by playing guitar in the video for her early track Longshot.

Perry began dating the late actor Johnny Lewis (Sons of Anarchy) in 2005. According to Us Weekly, an insider said that Perry could tell even then that he was headed down a “troubled path.” He was ultimately found dead in 2012, which the source said “devastated” her, adding that Perry’s tracks, The One That Got Away and Circle The Drain are partially about him.

According to Billboard, next to date Perry was Travie McCoy, the frontman of Gym Class Heroes. Their relationship was an on-again, off-again affair that was partly chronicled in Perry’s track, Circle The Drain. According to People, when announcing the split, McCoy posted a reference to a track from Main Source that has lyrics saying, “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.”

A mere blip on the RadarOnline.com ... according to E!Online, singer Mika (born Michael Holbrook Penniman) and Perry hung out at the Serpentine Gallery’s summer party in London in 2008 — and even left together. According to the Standard, Mika ran around with her on his back before they took off in a cab. Nothing even came from their night other than the fact that Perry turned up for a Radio One interview the following morning looking bleary-eyed.

Did they or didn’t they? It was rumored at the time that Perry was dating Josh Groban who was hot on the heels of his album Noel. According to Billboard, it was all denied at the time, but a few years later Groban said, “we might have skated on the line of dating.” And according to People, in 2017 Perry finally admitted Groban was the man she was writing about in her 2010 track, ‘The One That Got Away.’

Benji Madden was the shredder from Good Charlotte and according to E! Online, spent a night partying on Valentine’s Day, 2009. So were they a thing? Perry later blogged, “Oh kittens! It’s two pseudo famous people sitting next to each other … doesn’t mean we were bumping uglies.”

It was brief, and it wasn’t really talked about. But according to Tim Jones, the frontman for the Truth & Salvage Co, Perry did indeed date Maroon 5’s guitarist, James Valentine. Jones told E! Online that “We were up at his house one night and she was asleep.” As they worked on a piano track, Perry apparently woke up, asked what was going on, sang a few words, then went right back to sleep.

Perry met UK comic-actor Russell Brand at the MTV Music Video Awards, and within a year they were married with matching tattoos. Just 14 months later, according to ClassicFM, Perry told Vogue in 2016, “Let’s just say I haven’t heard from him since he texted me saying he was divorcing me December 31, 2011.” Brand later removed his tattoo.

Did they? Were they? Perry was suddenly being pictured on tabloid covers with the very handsome French model Baptiste Giabiconi. According to Billboard, they’d been friends for years and Perry even had to use Twitter to dispel the rumors saying she was “single and satisfied.” Which, on its surface, says nothing.

Gossip during the first half of 2012 was that Perry had started dating Robert Ackroyd — guitarist in Florence + The Machine. According to Billboard, she said it wasn’t even “appropriate to label” them a couple, “There are times I go out and meet people and flirt, but it’s not really appropriate to have anything serious.” It sounds very much like a spring fling.

The musician John Mayer met Perry and what followed was magic ... until it ended in 2014. But a happy — if not unusual — ending came in 2017 when, according to Billboard, Perry admitted that Mayer had been her best lover ever. Mayer responded by coolly saying, “I don't have a cool-enough thought for you.”

Is it true that during a Mayer pause Perry dated Robert Patt? No, she did not. She has been accused of dating Pattinson, but W is firm that the two are great friends, always have been and that’s it. When the pair first met each other they were both in loving relationships with other people.

The ripples from the “who’s your best and worst lovers” question Perry answered were still moving. That’s why Diplo, who dated Perry for a few months in 2014 and was named by her as her worst lover, understandably threw some shade her way. According to E! News, he responded with a curt, “I don’t even remember having sex.”

In August 2014, Perry attended the MTV Video Music Awards with Riff Raff. According to Bustle, that wound up adding fuel to the fire that had begun a few months back in March when each of them Instagrammed photos of a “date.” This was complicated by Riff Raff telling TMZ that it was "an average date situation" adding "who knows where things might go." Spoiler: They went nowhere.

Coachella was busy for Perry where, according to Hollywood Life, she spent time with Robert Pattinson, Diplo and Jared Leto. A source confided to OK! Magazine that “they both spent time at Coachella, and he’s trying to arrange a date, or at least a chance to hang with her alone.” If they did, no one saw.

According to Cosmopolitan, Perry was first seen acting flirty with Orlando Bloom at a Golden Globes party in January 2016. By the next month, they were vacationing in Hawaii. But it wasn’t all smooth sailing. In March 2017, they split up for a few months before the relationship began slowly heating back up again a few months later. On Valentine’s Day of 2019, they announced they were engaged. Who knows where this will go.