Should Kourtney Kardashian Date John Mayer?

Kourtney Kardashian is one of the most eligible bachelorettes in California. Between the fame (and bank account) that she’s earned over the years from starring on Keeping Up with the Kardashians and her brand-new lifestyle website, “Poosh,” Kardashian has got it going on.

She’s also seemingly quite single and might be ready to mingle – with a notoriously charming singer that might just have eyes for her as well.

Who has Kourtney Kardashian dated?

Kourtney Kardashian
Kourtney Kardashian | Michael Loccisano/Wire Image

Kourtney Kardashian’s longest relationship was undoubtedly with Scott Disick. The pair first met in 2006 and dated for years, even welcoming three children together. Kardashian and Disick were never married, although there was almost continuous speculation regarding engagement rumors and secret weddings.

The road for Kardashian and Disick was definitely a rocky one – Disick struggled with alcohol abuse and anxiety issues for years, and reportedly caused Kardashian a good deal of embarrassment. 

Finally, Disick and Kardashian broke up in 2015, shortly after having their third child, Reign. Although the former couple has managed to co-parent successfully since their split, with Disick joining the family for big vacations, there doesn’t seem to be anything romantic between them.

Kourtney Kardashian has dated a couple of people since splitting with Scott Disick, including model Younes Bendjima, but she hasn’t been in a serious relationship for some time.

Will she start dating John Mayer?

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Recently, Kardashian made an appearance on the Ellen show and played a game of “Who’d You Rather” with the talk show host. Ellen DeGeneres showed a revolving selection of different male celebrities and tasked Kardashian with choosing who she would prefer to be with and who she would eliminate.

Popular singer John Mayer kept popping up in each round, with Kardashian consistently choosing Mayer. In fact, Kardashian chose Mayer exclusively until the very last round of the game, when she ultimately chose both him and Leonardo DiCaprio – ending the game in a tie.

Needless to say, this sparked romance rumors between the unlikely pair and the tabloids have been buzzing with the idea that the eldest Kardashian sister could strike up a relationship with the chart-topping hitmaker. 

How does Mayer feel about her?

Kourtney Kardashian’s appearance on Ellen wasn’t the first time that romance rumors have arisen in regard to her and John Mayer’s relationship status.

In December 2018, Mayer and Kardashian had a run-in at a Hollywood party, and it seems that Kardashian made quite the impression on Mayer. Reportedly, they shared a flirty exchange that was noticed by a few, but they lost touch shortly thereafter.

Mayer definitely has impressive dating credentials. Over the years, he has dated such famous personalities as Jennifer Aniston, Taylor Swift, Katy Perry, Minka Kelly, and Cameron Diaz. He’s also a favorite party guest of many top Hollywood celebrities and runs in a very exclusive circle.

He and Kardashian certainly seem to have a lot in common – they have both been in the spotlight for a while, so they could relate to each other’s struggles with balancing fame and personal life. They are also age appropriate, with Kardashian having just turned 40 and Mayer an eligible 41 years of age.

Kardashian has three children, while Mayer has none, but he certainly seems sensitive enough to adapt well to step fatherhood, and could even get along well with Kardashian’s ex, Scott Disick.

Whether or not Kourtney Kardashian and John Mayer do start up a romance, there’s little doubt Kardashian’s appearance on Ellen will keep tongues wagging for quite some time. Only time will tell if Kourtney Kardashian decides to give love another shot with soulful, talented crooner John Mayer.