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Timeline: June 2012-February 2014For two years, Katy Perry and John Mayer were the music industry’s unlikeliest “it” couple. While the reason for their breakup is still unknown, one thing was for sure: it was definitely a little unsettling for fans to wrap their heads around this particular relationship, considering he’s 12 years her senior!

The pair had a pretty rocky off again, on again, and then permanently off again relationship between 20, before she moved on to date actor Orlando Bloom. Swift is known for writing tumultuous and heartbreaking songs about her previous relationships (many of which were high-profile), and John Mayer was no exception.

The girl in the dress who cried the whole way home,” it suffices to say that things didn’t exactly end amicably between the two.

Following that, Mayer wrote and then deleted a very snarky tweet on Swift’s birthday, arbitrarily stating: “Tuesday, December 13 may be the lamest day of the year, conceptually.”Obviously caught off-guard by the negative image painted of him in the song; Mayer said the song “made [him] feel terrible, because [he] didn’t deserve it.” He went on to say, “I’m pretty good at taking accountability now, and I never did anything to deserve that.

The Friends actress dated musician John on and off from 2008 until 2009.

As Jen finds herself back on the market following her shock split from second husband Justin Theroux, here's a look back at her dating history so far.

It was horrible, it was so tough man." Jennifer's first love was actor Daniel Mc Donald, who sadly died in 2007 from a brain tumour.

She previously said: "He would have been the one, but I was 25 and I was stupid." The couple dated from 1990 until just before her big break on Friends in 1994.

However Jennifer's rep denied the claims at the time and neither star confirmed the romance.

Jennifer was briefly engaged to actor Tate Donovan during their three year relationship from 1995 until 1998.

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