Years ago, on an episode of Keeping Up With the Kardashians, Kris Jenner ran into an ex-boyfriend named Todd Waterman at the Toluca Lake Tennis Club in 2012, according to People. This was when Jenner was still married to Caitlyn Jenner (then Bruce). When Jenner told Caitlyn, she was not pleased, to say the least, especially since Jenner began communicating with Waterman via email. But, the reason Caitlyn was overly upset was because, when Jenner was married to Robert Kardashian, she cheated on him with Waterman. Flash forward to season 15 of KUWTK. Jenner’s daughter, Kourtney Kardashian, reveals on the show that she still holds onto resentment about her mother’s affair.
According to The Daily Mail, Waterman and Jenner’s relationship began in 1989, which was about a decade into Jenner’s marriage with Kardashian. Waterman said that he had seen a photo of Jenner at a friend’s home and became attracted to her. He told The Daily Mail that, when they first got together, “I’m sure we danced and had a good time in the club. We came back to her friend’s home in Beverly Hills. And our first time [we had sex] was in her friend’s closet. We found a little place in the house and consummated the relationship. It was a magical night, surreal. I think it was two people who were both open to experiencing something in their life at that time. It was fate, we invited it and we just ran with it and from that point on. We didn’t hold back.”
Waterman continued, saying, “The love swept us away. We made our own different reality. It was special, it was a little crazy, a little wild – we didn’t exercise caution or self-restraint. I think we were both very much in love.” He said that once the affair came to light, he began attending events with Jenner as her boyfriend. And, Waterman also said that Kardashian hired private investigators to find out about the cheating. Waterman claimed that, on one point, there was a volatile exchange, which resulted in a brief car chase. Jenner was reportedly in a car with Waterman and Kardashian was “trailing” them.
Jenner wrote about Waterman in her book “Kris Jenner … And All Things Kardashian” and referred to him as a young soccer player named “Ryan”. Also in her book, Jenner said that her affair with Waterman was filled with passionate sex.
On KUWTK season 15, Kourtney Kardashian brings up issues from the past, surrounding the affair, as reported by People. According to Waterman, he felt that Kourtney took the news of the affair, and the divorce between her parents, the hardest of all the kids. Waterman told The Daily Mail that, ” think it affected Kourtney the most. I know she was definitely affected and I always felt bad about that. She was the oldest. Kimberly didn’t seem to mind and Khloe she was just a special kid.”
Waterman said that he most regrets the pain he caused Robert Kardashian and his kids. Meanwhile, Jenner has said she regretted the affair altogether. In 2016, on her TV series Kocktails With Khloe, Khloe Kardashian talked about the remorse her mom had over the affair and how it affected her father. Khloe Kardashian revealed that, “I saw how it destroyed my dad. I saw what it did to my dad, so I don’t want to do that. I also saw the regret from my mom.”
As for what made Jenner cheat on Robert Kardashian, she explained on OBJECTified that, “I married Robert when I was 22 years old and I got pregnant on my honeymoon — I had the happiest life you could’ve dreamt about. But when you’re in something, sometimes people think the grass is always greener and that was like what I think I went through at some point.”
Today, Todd Waterman works as an animator.