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

They had a brief split in August 2008 until the October, with John bizarrely holding a press conference to reveal he ended it because "something's not right.

JENNIFER Aniston is one of the most beautiful women on the planet, so it's no wonder she's had hunky men knocking her door down to date her over the years.

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.

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.

That sparked a lot of speculation that their feelings for one another might be more than just platonic. She may be seven years younger than him, but that didn’t stop the two of them from enjoying some much-needed quality time together!

Depending on how you look at it, John Mayer has either been very lucky or unlucky in love.In a totally awkward, yet entertaining singer looked absolutely mortified and refused to answer the question at first, but complied with a non-verbal gesture, uncharacteristically shying away and averting her eyes from the camera. The timely release of the song proved that their relationship wasn’t as peachy as the pair made it seem.When asked about this funny moment during an interview with magazine, Mayer had a very down-to-earth and nonchalant response: “I don’t have a cool-enough thought for you. With lyrics like, “Don’t you think I was too young to be messed with?Tate even starred in Friends as Joshua, who dated Jennifer's character Rachel, but the couple were breaking up in real life at that point.Tate said: "I thought maybe it will be good to work through this break up, what an idiot, it was bad.