Let’s be real: John Mayer is almost as well-known for his long list of gorgeous ex-girlfriends as he is for his music.
The dude has definitely a garnered a rep as a womanizer — and one who likes to kiss and tell, at that. But was he really just doing research on what not to do when he finally found “the one”?
Mayer himself even said last year that he might be ready to get serious. Here are the women who may have helped make him boyfriend material.
Originally published June 2016. Updated July 2017.
Katy Perry
Katy Perry has a thing for bad boys who are willing to show their soft side, so it’s absolutely no surprise that she had a thing for Mayer. The pair had a very confusing on-again, off-again relationship, but it seems to be finally off for good with Mayer ready for a new girlfriend and Perry dating Orlando Bloom.
Renee Zellweger
Back in 2011, Zellweger spent some time with Mayer in New York City. Nothing serious ever came of their hang sessions, but that’s probably because Zellweger knew exactly what she was getting into and kept it strictly fun while they were seeing each other.
Taylor Swift
As things tend to do with Taylor Swift, this was a very quick romance that got messy. The two dated quietly in late 2009, but Mayer played “dark and twisted games” with Swift that were just too much for her. In the end, she got “Dear John” and “Story of Us” out of the fling, so it wasn’t all bad.
Kim Kardashian
Kim Kardashian took a quick detour from her professional athlete or hip-hop legend-type for a fling with Mayer in October of 2010. These two spent some time having fun (one of his favorite pastimes) in New York City that fall, but nothing serious ever came of it. And, really, who didn’t see that coming?
Scheana Marie
Before she was causing drama on Vanderpump Rules, Scheana Marie was just a cocktail waitress in New York City hanging out with the “really cool guy” Mayer. Unfortunately, one of Mayer’s deal breakers is talking to the media, so when Marie gave an interview to Young Hollywood, he called it off.
Jennifer Aniston
This one hurt the most for those of us who aren’t charmed by Mayer’s playboy status. For nearly a year in 2008 and 2009, Mayer and Jennifer Aniston were a full-blown couple. They went on red carpets together and even when it was over, Mayer talked openly about how much he wished they could still be together. Aniston will apparently always be his one that got away.
Minka Kelly
Back in 2007 when things were a little less complicated, Mayer and Minka Kelly looked like a couple of college kids in love. They only dated for a couple months before she moved on to megastar Derek Jeter, but managed to be inseparable for their short relationship.
Jessica Simpson
This was the tipping point where Mayer turned from a sweet guy you’d be lucky to date to kinda creepy. He and Jessica Simpson got together on the heels of her divorce from Nick Lachey. They stayed pretty quiet during their year romance, but after their breakup in May 2007, Mayer publicly discussed their sex life, telling Playboy, “That girl is like crack cocaine to me. Sexually, it was crazy.” Not your best move, Mayer.
Rhona Mitra
Not much is known about how Rhona Mitra and Mayer met or why they didn’t work out, but in 2005, rumors were swirling that these two had hooked up. Neither one addressed the rumors, so we may never know the truth of this one.
Jennifer Love Hewitt
Right before Mayer really hit it big with his single “No Such Thing,” he was in a very serious relationship with Jennifer Love Hewitt. Although they didn’t last long after his fame started to rise, it is rumored that Hewitt is to thank for Mayer’s song “Your Body is a Wonderland.”
Vanessa Carlton
Strangely, Vanessa Carlton and Mayer’s romance wasn’t public until a scene in Pitch Perfect 2 where the groups were singing songs by women who Mayer has dated, and “A Thousand Miles” came up. Turns out, in 2001, right after he broke up with Hewitt, he and Carlton dated for about a year. They’ve been tight-lipped about the whole thing, but she fits his type, so it definitely sounds true.
Cameron Diaz
Mayer’s pairing with Cameron Diaz was the definition of two stars just hanging out and having fun. They spent time together in New York City after Diaz called it quits with her longtime love Justin Timberlake. She was probably nursing a broken heart, so nothing serious ever happened.
Rashida Jones
Rashida Jones was spotted hanging out with Mayer in 2009 after he split with Aniston. Mayer may have still had feelings for Aniston, because their fling ended pretty quickly and quietly. She was too busy being super successful on Parks and Rec.
Colbie Caillat
In the summer of 2009 (a very busy year for Mayer), he and Colbie Caillat were rumored to have hooked up. It is entirely possible that these two singer-songwriters were simply discussing a future collaboration, but since we haven’t heard anything come from the two, we’re going to say it was a few dates that just didn’t work out.
Mandy Moore
For a brief time after dating Simpson, Mayer and Mandy Moore were a rumored thing. Although her reps denied that their relationship was anything more than a fling, based on her ex-husband, Ryan Adams, it looks like Mayer is her type.
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