10 of Katy Perry's Ex-Boyfriends — From Russell Brand to Orlando Bloom and More

Katy Perry's first known boyfriend when she started her career was Paramore guitarist Taylor York's brother Justin York. She was 17 years old when they began dating, though it remains unknown when things ended between them.

Perry based her famous tracks "Circle the Drain" and "The One That Got Away" on her relationship with Johnny Lewis.

She dated the Sons of Anarchy actor for a year from 2005 to 2006, and she was left devasted by his death in 2012 when he fell from a rooftop after murdering Catherine Davis, his 81-year-old landlord.

In 2006, Perry struck a romance with Travie McCoy. They worked together on the "Cupid's Chokehold" music video and continued dating until she got more famous when "I Kissed a Girl" was released.

Although she called it quits via email, McCoy knew his struggle with drug addiction contributed to their breakup.

"She wasn't stupid. She knew when I was f----- up," he said during a 2012 Behind the Music special. "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."

Perry and Josh Groban sparked dating rumors in early 2009, but their representatives dismissed the buzz.

According to the "You Raise Me Up" singer, what they had was platonic – but Perry referred to him as "the one that got away."

The entertainer met her first husband, Russell Brand, at the MTV Video Music Awards. They got engaged roughly three months later and tied the knot in October 2010.

Brand – who has been accused of rape, sexual assault and abuse by several women – filed for divorce in December 2011, citing "irreconcilable differences."

For two years, John Mayer and Perry shared an on-again, off-again relationship until they broke up for good in 2014. They reunited again the following year, but they split again afterward.

The "You're Gonna Live Forever in Me" crooner told Ellen DeGeneres that he did not want to share what went wrong between them, but he clarified he had been much happier after they called it quits.

Perry and Diplo were so private about their relationship that they shocked everyone when they suddenly split in March 2015. They initially sparked dating rumors after spending time at the 2014 Coachella and during the premiere of The Amazing Spider-Man 2.

The "Firework" songstress and Orlando Bloom met in 2013, but their paths did not meet again until the CAA's 2016 Golden Globes after-party at Sunset Tower in January 2016.

From there, they dated until February 2017 before resuming their romance in January 2018.

The pair have been engaged since Valentine's Day 2019.