Katy Perry Has A Pretty Strange Love Life

Katy Perry is full of drama. Though the singer tends to keep her private life mostly private, what we do know about it is somewhat bizarre, sometimes unsettling, and often sounds sort of ... miserable.  Here are the oddest aspects of the "Chained to the Rhythm" chanteuse's love life and the twist that could bring her a happily ever after. 

Back when Katy Perry was still Kathryn Hudson, she dated Relient K frontman Matt Thiessen from 2003 to 2006. Ever the supportive girlfriend and glutton for attention, Perry ran across the stage during one of the band's performances of a cover of "Lose Yourself" by Eminem. First she flailed around with a sign, then decided to hurl herself into the crowd in an attempt to stage dive ... and it didn't end well for her.

The duo recorded "Long Shot" while dating. It never ended up on any of Perry's albums, but she sold the song to Kelly Clarkson, who slayed it on her 2009 album All I Ever Wanted. Thiessen and Perry have reportedly remained friends for years and Thiessen later contributed to her song "Dressin' Up" from Teenage Dream: The Complete Confection.

Before becoming a household name, Katy Perry dated actor Johnny Lewis from 2005 to 2006. In 2012, Lewis died after falling from a roof — but not before he allegedly beat his landlady to death and killed and dismembered her cat, TMZ reported. Lewis reportedly suffered from drug addiction, and sources told the site that he may have been under the influence of methamphetamine or PCP at the time of the incident.

An insider told Us Weekly that Perry was "devastated" by Lewis' death. "She had to separate from him ... to get ahead and focus on her career," the source said. "He was in trouble then and she couldn't help him. 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 [McCoy]. 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."

Perry and her first public boyfriend, Travis "Travie" McCoy, were serious enough to have promise rings and date for more than two years, even making appearances in one another's music videos (a snoozing McCoy appears in "I Kissed A Girl" and Perry is McCoy's true love in "Cupid's Chokehold.") Given all that history, imagine his surprise (and hurt) when she supposedly dumped him over email in May 2009.

McCoy recalled their romance on Behind the Music (via Contact Music): "We looked really cute together. We [got] 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 ... When I was around her I felt really at ease and comfortable with myself ... It was the most amazing thing ever." He also opened up about the end, fuming: "[The email] started off with 'I love you so much I hate to do this, blah blah blah.' Someone that you are ready to spend the rest of your life with sends you a f**king email just s**tting on your whole parade. It destroyed me."

In Perry's song "Swish Swish," she sings, "And karma's not a liar / She keeps receipts." She may have learned that lesson the hard way: A little over two years after she dumped McCoy over email, her husband, actor Russell Brand, told her that he wanted a divorce ... via text message. "[Brand is] a very smart man, and I was in love with him when I married him," She told Vogue. "Let's just say I haven't heard from him since he texted me saying he was divorcing me December 31, 2011." Another one in the basket, eh?

Perry told Vogue that her intense tour schedule for Teenage Dream was a factor in her divorce, but there were also some unnamed, sinister elements at play as well. "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," she said. "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. I let go and I was like: This isn't because of me; this is beyond me. So, I have moved on from that."

That "real truth" may be Brand's alleged infidelity. One of Perry's best friends, Markus Molinari, tweeted in March 2012: "Seeee Russell! ... Cheating is easy, try doing something challenging and be faithful." For his part, Brand has adamantly denied any philandering during the brief marriage.

Perry had allegedly been dating actor Orlando Bloom for just one month when she met his son, Flynn, with ex-wife Miranda Kerr. That may seem a little fast, but it wasn't the first time she moved at lightning speed.

Perry and Russell Brand got engaged in January 2010 after dating for just four months and tied the knot in October 2010 after just over a year together — only to file for divorce just 14 months after that. In March 2012, she was linked to male model Baptiste Giabiconi. One month after that, in April 2012, she was spotted getting cozy at Coachella and Los Angeles hotspot Chateau Marmont with Florence and the Machine guitarist Robert Ackroyd. By August 2012, she'd hooked up with musician John Mayer for the first of many times.

Perry was awarded the Human Rights Campaign's National Equality Award in 2017, nine years after "I Kissed A Girl" was released in 2008. Until then, Perry had never really admitted whether or not she ever kissed a girl (and liked it), but in her acceptance speech, she said she did — and more.

"Truth be told, I did more than that!" However, Perry claimed that her religious upbringing limited her exposure to the LGBTQ community, noting (via People), "But how was I going to reconcile that with the gospel-singing girl raised in youth groups that were pro conversion camps? What I did know was that I was curious, and even then I knew that sexuality was not as black and white as this dress. But in 2008, when that song came out, I knew that it started a conversation that a lot of the world seemed curious enough to sing along to it ... These people were nothing like I had been taught to fear."

"They were the most free, strong, kind, and inclusive people that I have ever met," she continued. "They stimulated my mind, and they filled my heart with joy, and they danced with joy while doing it. These people are actually, magic, and they are magic because they are living their truth."

Perry's on-again-off-again romance with John Mayer seems nothing less than exhausting. They reportedly got together in early August 2012, then reportedly split before the month was even over. On Sept. 1, 2012, they were spotted together again, and they kept going strong, with Perry even rocking a very visible heart-shaped ruby ring during a date with Mayer on Valentine's Day 2013. However, by March 2013, they'd called it quits. In June 2013, they reunited for a "casual" relationship. At the time, Perry told Marie Claire that she hadn't processed the fallout of her divorce from Russell Brand, which hurt her romance with Mayer and led her to take a break from the relationship.

They conveniently got serious again by August 2013, when their duet, "Who You Love," dropped. By October 2013, sources speculated that they'd get engaged, and one month later, Perry was seen wearing a diamond ring on that finger. Neither she nor Mayer confirmed or denied an actual betrothal. In February 2014, they reportedly split again but were spotted on a date in January 2015 and appeared to be decidedly back on by summer 2015. They even partied together on New Year's Eve that year.

Perry told Vogue in 2013 that her on-again off-again romance with Mayer was the real deal, but that it was also part of a pattern in her dating life overall to go after bad boys. "I was madly in love with him. I still am madly in love with him," she said in the July 2013 issue. "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."

In 2017, she told Vogue that she's not necessarily looking for a second husband now that she's in her 30s. "It's a nice place to be. I love it! I wouldn't give anything to go back to my 20s; I'm so much more grounded. And I've learned a lot of lessons — patience, the art of saying no, that everything doesn't have to end in marriage. That your education can start now."

She's apparently singing a different tune now...

Katy Perry reportedly began dating Orlando Bloom in January 2016, but a source close to the actor told People that he was "still keeping his options open" throughout his relationship Perry. It's unclear if they were on the same page about that. An insider told Radar Online that "Orlando never changed his ways with hanging out with other women [during the relationship]. He would still continue to hang out with his actor buddies and there were always a ton of sexy women around."

Bloom was even photographed in some compromising positions with other ladies before he and Perry announced their breakup. In May 2016, TMZ snapped Bloom hugging and allegedly kissing much-younger pop star Selena Gomez in Las Vegas, though witnesses later insisted that Gomez went back to her hotel room alone. On March 1, 2017, the Daily Mail published photos of Bloom cozying up to Erin McCabe, a daughter of Global Green President Les McCabe. Bloom reportedly rubbed Erin's backs and even swapped place cards with other guests at a gala to sit together. Six days later, he and Perry released a joint statement announcing they were dunzo ... at least for a while.

Katy Perry and Orlando Bloom eventually found their way back together. Here's how, courtesy of Vulture: "Bloom would go on to paddleboard naked (a decision Perry would need a lot of therapy to cope with) and casually date Nina Dobrev; Perry would go on to rank Bloom's sexual performance second out of three of her past exes (Diplo was No. 1) and kind of date Robert Pattinson. But all of that's water under the paddleboard you're standing naked on, as they say, and the two began dating again in early 2018."

The following year, they had a Valentine's Day for the memory books. On Feb. 15, 2019, she shared a photo starring Bloom and another character — or should we say carat-er? Perry captioned her Instagram snap: "full bloom," and there's no overlooking her flower-shaped diamond ring. Bloom later shared the same snap with the caption: "Lifetimes." Yup, for real. WP Diamond President Andrew Brown told E! News that Perry's ring "would retail in the range of $5 million." He said it appears to be "a 4-carat fancy vivid pink oval shaped diamond arranged with eight white diamonds around it to assemble a flower 'in bloom' — this ring is truly one-of-a-kind and wildly valuable."

The journey to this engagement may not have been a fairy tale, but we're certainly thrilled to see these two joyously celebrating their future plans together.