Image via Complex Original
Recently, it's been rumored that notorious tinsel town Lothario John Mayer is now dating Katy Perry, the newly single and smoking hot former Mrs. Russell Brand. The pair were first spotted together last month, being openly touchy-feely while in the water at a Beverly Hills pool party.
Lucky as Mayer may be, this news comes as no real surprise, as the serial dating singer-songwriter has bagged an impressive list of famous hotties throughout the last decade.
Colbie Caillat
When: August 2009
In 2009, on the heels of her hit single "Bubbly", California girl Colbie Caillat was rumored to have hooked up with the Hollywood playboy. As they're both singer-songwriters with a similar laid-back vibe, it's entirely possible that, just maybe, they were together discussing a future collaboration. But as it's now 2012 and no such duet has surfaced, we're of the opinion that any beautiful music made here wasn't done in a studio, but between the sheets.
Smash Probability: If you're a gambler, and we are, one thing is certain: Much like you should always double down on 11 in blackjack, you should never bet against a John Mayer hook-up.
Cameron Diaz
When: December 2007
In 2007, Mayer set his sights on the stunning and bubbly Cameron Diaz. They quickly hit it off, as Mayer and the former Charlie's Angel were seen cuddling next to a crackling fireplace at New York City's swanky Bowery Hotel. This one we totally get. There's something about Cameron Diaz.
Smash Probability: Getting cozy near a fire in New York City at Christmas time? We know what happens next.
Jessica Simpson
When: May 2006 - May 2007
Soon after her high profile breakup from ex hubby Nick Lachey, Jessica Simpson rebounded with fellow musician Mayer. The two dated for nearly a year. On the 2007 Grammy Awards red carpet, Ryan Seacrest asked Mayer about his relationship with Simpson, but Mayer cryptically responded in Japanese. After their May 2007 breakup, Mayer famously dished about the couple's sex life in a notorious Playboy interview.
Smash Probability: Mayer's quoted in Playboy as saying, "That girl is like crack cocaine to me. Sexually, it was crazy." That pretty much says it all.
Taylor Swift
When: November 2009-January 2010
They say hindsight is 20/20, right? Well in retrospect, perhaps old Johnny boy should have left this one alone. Though the pairing initially seemed to be a match made in attractive musician heaven, it didn't end so well. After the couple's tumultuous break up in 2010, Taylor let her feelings on the situation be known in the only way she knows how: She sung about it. She released a song, the aptly titled "Dear John," in which she detailed Mayer's "dark twisted games".
Smash Probability: Taylor didn't book studio time to vent about the dude for nothing.
Mandy Moore
When: June 2007
After his relationship with Jessica Simpson ran its course, John was briefly rumored to be dating another pop star-turned actress, the gorgeous Mandy Moore. Before she got hitched to crooner Ryan Adams, Ms. Moore had been linked to her fair share of famous beaus, so if this hook-up turned out to be true, it wouldn't shock us in the least. However, once the news broke, Moore's reps quickly dispelled this relationship as nothing more than friendship.
Smash Probability: Let's be honest here, no PR firm is putting out a press release saying "Yes, my client is boning John Mayer," so her reps' statement means nothing to us. But, since the claim has been outright denied, we'll give Mandy the benefit of the doubt.
Jennifer Aniston
When: April 2008-March 2009
In 2008, John entered into what soon became a high profile relationship with Jennifer Aniston. Though the former Friends star and Hollywood heavyweight is nearly ten years older than John, the two enjoyed a storybook romance for the better part of a year. Since their split, John's been quoted as saying, "I'll always be sorry that it didn't last. In some ways, I wish I could be with her." Sorry, John, she just got engaged to actor/director/screenwriter Justin Theroux. Will Jennifer Aniston wind up being the one who got away? Time will tell.
Smash Probability: We'd be hard pressed to believe that these two were just...friends.
Kim Kardashian
When: October 2010
In late 2010, prior to her 45 minute "marriage", Kim Kardashian was seen hitting the town in NYC with none other than John Mayer. Between the two of them, this pair of serial daters have been linked to half of Hollywood. Nothing of note seemed to materialize as far as a relationship goes, but they were spotted spending a fair amount of time together that fall. The curvy reality vixen was quoted as saying that Mayer's a "really cool guy".
Smash Probability: A sex tape wasn't released and he never appeared on her E! series, so who knows?
Katy Perry
When: July 2012-Present
John sure does have a thing for musicians, doesn't he? Actually, what are we talking about? He'd probably have dated Katy Perry if she worked as an Arby's fry cook in south Jersey. John Mayer just likes hot chicks, and we can't fault him for that.
Perry is Mayer's most recent hook-up and the two have been spotted everywhere together—from candle-lit dinners, to drinks at the Chateau Marmont, to swanky pool parties.
Smash Probability: She's his summer fling. You'd get as much as you can done, too, if you only had three months.
Jennifer Love Hewitt
When: September 2001 - June 2002
Not only did John date this former Party Of Five star, but it's been rumored that his breakout single "Your Body Is A Wonderland" was actually inspired by her. For the record, whether it was or not, we agree that her body is. The two dated for the better part of a year in 2002, and it's said that the relationship fizzled due to John's rigorous touring schedule that year.
Smash Probability: They dated for almost a year. Come on.
Minka Kelly
When: September 2007 - December 2007
Before he began dating Jennifer Aniston and before she linked up with Mr. 3,000 himself, Derek Jeter, Mayer was rumored to be dating the adorable Minka Kelly. The relationship didn't last long, and it's said that Mayer was actually the one who ended it. Yes, you read that right, Minka Kelly was dumped. Wow.
Smash Probability: While we doubt most John Mayer dates end in a peck on the cheek and an "I'll call you next week", he did break up with her. Perhaps she was playing hard to get?
