"Google me" was the simple answer John Mayer once told a fan in 2019 when he was asked why he was still single. However, most people don't have to search his name to know that he's been labeled one of Hollywood's most infamous playboys.

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The "New Light" singer is known for his long list of relationships with A-list women, including several exceptionally talented actresses and singers. There was Jennifer Love Hewitt, Jessica Simpson, and Taylor Swift, and that's only naming a few ladies who fell for his charm. While his relationship status is up in the air as of now, it is interesting to take a closer look at his past romances and see who were some of the most famous ladies he's dated.

10 Vanessa Carlton

One of John Mayer's first high profiled romances was with singer Vanessa Carlton in 2002, while the two were just making a name for themselves in Hollywood, according to Wonderwall. Carlton released "A Thousand Miles" a year before, and Mayer released one of his most popular jams, "Your Body Is A Wonderland."

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The two singers seemed like a perfect match, with Carlton's song seemingly about the guitarist, but sadly, they parted ways after just dating for a year. Mayer may have been loving the attention other Hollywood women were giving him as his career blossomed, like the one we're about to mention below.

9 Jennifer Love Hewitt

In 2002, John Mayer would also go on to date Jennifer Love Hewitt, and rumors were swirling that his song, "Your Body Is a Wonderland" was about her. However, the song came out in 2001, so it made absolutely no sense that the song was about the actress, as much as the media wanted it to be.

Still, Hewitt commented on the compliments she received about the misconception, stating, "My body is far from a wonderland." Their relationship was brief and Mayer quickly moved on.

8 Jessica Simpson

John Mayer and Jessica Simpson began dating around 2006, when the songstress's marriage ended with Nick Lachey, according to E! News. While the relationship only lasted a year, Mayer went on to say some highly inappropriate things about the former couple's physical romance that he later ended up regretting.

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The Hollywood couple broke up for good in 2007, and Simpson included her ex in her 2020 memoirOpen Book, writing, "He'd walk into a room and pick up his guitar and you'd swoon."

7 Cameron Diaz

In 2007, Cameron Diaz and John Mayer were rumored to be a couple after they both had just got out of very high profile relationships. Diaz just broke up with Justin Timberlake and Mayer ended things with Jessica Simpson, according to Wonderwall.

It was revealed that the two were "super flirty" while out and about in New York City, but nothing seemed to come out of the relationship, and Mayer quickly moved on to another Hollywood actress.

6 Minka Kelly

According to E! News, by the fall of 2007, John Mayer already had his eyes on actress Minka Kelly. However, this relationship would also be short-lived and it was over as soon as it began. The two called it quits around New Year's of the same year and neither one of them spoke about the relationship.

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At the time, a source told People, "Minka told a couple of friends that she and John had broken up but she really didn't want to tell anyone." This relationship would also seem to be just a notch on Mayer's belt.

5 Jennifer Aniston

Everyone believed that John Mayer was going to be the man to rescue Jennifer Aniston from her divorce from Brad Pitt. The two dated in 2008, broke up for a bit, and then reconciled in 2009. However, it would be just another brief romance for Mayer, who later admitted that he will "always be sorry that it didn't last." Telling Playboy in 2010, "In some ways I wish I could be with her. But I can't change the fact that I need to be 32."

4 Rashida Jones

Actress Rashida Jones supposedly dated John Mayer around the same time he was ending things with Jennifer Aniston in 2009. E! News reported that Jones and Mayer were spotted in October of that year attending a charity event together, but both were seen arriving 45 minutes late, prompting the media to believe they were more than just famous friends.

However, no new information came to light about this potential couple, and it appeared that gossip sites were just trying to pin these two together after a friendly night out.

3 Taylor Swift

John Mayer and Taylor Swift were linked in 2009 after they recorded "Half of My Heart" for his album, Battle Studies. While the couple never confirmed they were dating, (Swift was 19 at the time, while Mayer was 32), she pretty much made it known that they were once an item after releasing her song, "Dear John," in 2010, with lyrics that read, "Don't you think  I was too young to be messed with?"

In an interview with Rolling Stone, Mayer expressed his frustration about the song, calling it "a really lousy thing for her to do," and that at the time, it "humiliated" him.

2 Renee Zellweger

One of his most secretive relationships was with actress Renee Zellweger, in which they supposedly dated in 2011. It seemed like fans would never speculate putting these two together, but apparently, they had a quick romance after they were seen in New York City, grabbing dinner and enjoying the sights, according to Noteabley.

However, just like many of his past relationships, nothing more came out of this one.

1 Katy Perry

One of John Mayer's most promising romances was with Katy Perry, who he dated on-and-off from 2012 until 2015. Perry even told in 2013, "I actually am dating my crush," and their relationship seemed to be getting more serious.

But, once again, Mayer would not give in to the idea of settling down, and their relationship was over for real this time, and Perry moved on with actor Orlando Bloom in 2016.

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