How Kim Kardashian Absolutely Broke Nick Cannon's Heart

Before marrying Kanye West, Kim Kardashian dated her fair share of celebrities, such as Kris Humphries (whom she married and divorced just 72 days later), Reggie Bush, and Ray J. Still, there's one celeb ex you might have forgotten about: Nick Cannon. Per the Mirror, Cannon and Kardashian dated from September 2006 until January 2007, just before her infamous sex tape with Ray J hit the internet.

In a 2018 interview with DJ VLAD, Cannon discussed his past relationship with the former reality star and revealed that she was somewhat insecure about the way she looked. "I remember, like, she didn't like her nose," he said. "I was like 'Yo, you're beautiful,' but like, they grew up in Beverly Hills, where kids were getting plastic surgery before their facial features even fully developed." Cannon even took credit for introducing Kardashian to her future husband, Kanye. "Me, Kim, and Paris Hilton went to a club in New York, Lil Kim was there," he continued. "Kanye came to my table and I was like 'Yo, meet my chick, Kim.'"

According to Kardashian, however, she and Cannon were never serious (ouch!). "We were never really ... we were always friends," she told Complex in 2007. "He was someone who I enjoyed spending my time with, but we were never really a couple. And I think it fizzled out way before that even happened." Whether they were in a committed relationship or not, Cannon did admit that the Armenian beauty completely broke his heart.

In an October interview with "Drink Champs," Nick Cannon spoke about dating Kim Kardashian and what ultimately led to their breakup. "I remember I was really into her," he told podcast hosts N.O.R.E. and DJ EFN (via the Daily Mail). "We was on some serious s***!" Then, he revealed that "she broke [his] heart."

While the two were dating, rumors of a sex tape featuring Kardashian started circulating in Hollywood, so Cannon asked if it was true. "When I asked her about it, she denied it," he said. Before that, the two ran into Ray J, who seemingly teased the "Masked Singer" host. "I was holding [Kim's] hand and, literally from across the street, he was like 'You ain't gonna wanna keep holding her hand soon, watch!' ... And I'm like wondering why he said that, and then there started to be these little rumors around that there was this tape," Cannon continued. "I think he was warning [me]." 

This isn't the first time the TV host has spoken about Kardashian's sex tape scandal. "If she might have been honest with me I might have tried to hold her down," Cannon told Howard Stern in 2012 (via HuffPost). "She's actually one of the nicest people you'll ever meet," he continued. "But the fact that she lied and told me that there was no tape? And I still think she might have even had a part to play with [its release]."