Kendall Jenner

The internet went into meltdown in November 2013 when he was first spotted having dinner with model Kendall Jenner in Los Angeles. Though their romance only lasted a few months, this wasn’t the last time the pair were romantically involved.

In 2016, they were spotting spending New Year's together on a yacht in St. Barths.

A week later, the model’s sister Khloé Kardashian confirmed the rumors and told Entertainment Weekly that the two were dating.

She said: "Do I think they're dating? Yes. I don't know if they're like boyfriend-girlfriend. Nowadays I don't know. People are weird with stuff. So, I don't know their title."

They eventually broke up in late 2016, but remain friends.