1 / 15VIEW ALL
Mayer briefly dated Vanessa Carlton as they both started inching their way towards their successful careers, though their love affair was short and sweet after Mayer laid eyes on the gorgeous Jennifer Love Hewitt.
Jennifer Love Hewitt
2 / 15VIEW ALL
When: 2002 - 2003
Right before Mayer stepped into the lime light, he was head over heels in love with the Ghost Whisperer actress. In 2002, Mayer released his second single from his first album, "You're Body Is a Wonderland", which was apparently dedicated to Love Hewitt. The couple broke up when Mayer went on tour and became too busy for a relationship.
3 / 15VIEW ALL
Though we aren't sure if the pair actually dated, rumors sparked that the British actress and model hooked up with Mayer for a few months. Both parties tried to keep their fling under wraps.
4 / 15VIEW ALL
The Life Happens star was one of Mayer's many casual flings. Clearly Mayer likes them young because Vayntrub was only 19 when the 28-year-old musician was rumored to be hooking up with her.
5 / 15VIEW ALL
After her split with Nick Lachey, Simpson and Mayer dated for nearly a year. Shortly after their breakup, tabloids exploded when Mayer compared Simpson to "crack cocaine" in an interview with Playboy. He even went on to say that, "sexually it was crazy" and that "it was like napalm, sexual napalm." #nofilter
6 / 15VIEW ALL
Right after he ended things with Jessica Simpson, Mayer was briefly seen flirting around with Cameron Diaz, who at the time had just called it quits with Justin Timberlake. Perfect timing to meet someone new right? People reported that the duo was seen in New York City, and a source confirmed that they were in fact dating, though their romance faded pretty quick.
7 / 15VIEW ALL
Derek Jeter's ex and Friday Night Lights alum Minka Kelly casually dated Mayer before he left her to be with Jennifer Aniston. How the two still manage to be friends? We will never know.
8 / 15VIEW ALL
The on again off again couple dated for about a year before they finally called it quits. Apparently Mayer wrote "Shadow Days" about Aniston and years later still felt sad about their break up. "That woman was the most communicative, sweetest, kindest person," he told Playboy. It sounds like Jen might have been the one that got away.
9 / 15VIEW ALL
Mayer completely denied having any history with Scheana Marie, though the reality star said otherwise. In a video interview, Just Jared asked the then 23-year-old if John was a good kisser. She gushed and replied that she thought he had nice lips. She dropped other subtle hints throughout the interview about the pair being intimate, but no one truly knows if anything actually happened.
10 / 15VIEW ALL
Of course, Mayer is one of the many bad boys that broke T-Swift's heart. After their breakup, rumors sparked that Swift's "Dear John" was actually written about Mayer. In the song Swift refers to how poorly "John" treated her and broke her heart. She even calls him out for his "dark twisted ways." Poor T never catches a break.
Later Mayer admitted to Rolling Stone that the song made him feel "really humiliated". He then added, "I didn't deserve it. I'm pretty good at taking accountability... It was a really lousy thing for her to do." Whatever helps you sleep at night, dude.
11 / 15VIEW ALL
The Parks and Rec actress was seen out and about with Mayer enough times to spark dating rumors. Sources told E! that their relationship was completely platonic, but still managed to catch the media's attention. The rumors eventually fizzled out.
12 / 15VIEW ALL
Before Miley and Liam Hemsworth found each other, according to Glamour, the "Wrecking Ball" singer briefly dated Mayer. That may explain why Cyrus threw Katy Perry some serious shade back in 2014 about her relationship with John Mayer. Maybe she still had some hard feelings.
13 / 15VIEW ALL
The pair was seen partying in NYC together while Kim K was shooting an episode of Keeping Up With The Kardashians. According to Page 6, both brought friends along to test out the waters and see if there was actually any chemistry between them.
That being said, Mayer did not take kindly to rumors of the couple hooking up, and apparently tweeted, "I see @kimkardashian at Sirius/XM and say hello like a gentleman and you want to spin a story at my expense? F**** You!" Yeesh! We'll never know what actually happened, but considering both their reputations as serial daters, we wouldn't be surprised if the rumors are true.
14 / 15VIEW ALL
The British makeup artist dated Mayer for a short time, though their relationship was nothing serious. They quickly went their separate ways and Hammer went on to date The Tudors' Jonathan Rhys Meyers.
15 / 15VIEW ALL
When: 2012 - 2015
Shortly after finalizing her divorce with Russell Brand, the "Dark Horse" singer moved on to Mayer. She told Entertainment Weekly that the pair had exchanged love letters long before their relationship went public. Aw!
But like all John Mayer relationships, this love story came to an end too. After being on and off for three years, the couple parted ways because of conflicting schedules and trust issues. Though things are looking great for Perry who was currently seen frolicking around Coachella with Orlando Bloom. You go, girl!