Details About Rihanna And Rob Kardashian's Short-Lived Fling

Rob Kardashian almost made a love connection with Rihanna.

In December 2020, an insider spoke to Entertainment Tonight and shut down any speculation that Kardashian was scouting for a new girlfriend. While Kardashian "would love to find a great woman to date, he's just focused on being a good dad, hanging out with loved ones, and keeping things private." The insider continued, "Rob is hands on when it comes to being a dad and prioritizing [6-year-old daughter] Dream."

However, Kardashian was definitely invested in finding his better half in the past. Rita Ora, Adrienne Bailon, and Blac Chyna are just a few of Kardashian's famous exes. And while he hasn't dated Ora and Bailon for several eons now, his relationship with Blac Chyna played out more recently. Fortunately, after years of feuding, the parents are over the drama. When appearing on "Sway In The Morning," Blac Chyna spoke about her relationship with Kardashian and Tyga (the father of her oldest child). "We are getting older, and I am just grateful for my kids," the socialite said. "So I will always have that respect for them, and vice versa. There's more to Kardashian's dating history, however. Years before the Arthur George founder became a father, he briefly dated Rihanna. Yes, that Rihanna.

In 2012, TMZ reported that Rihanna and Rob Kardashian went go-carting and visited a local Los Angeles nightclub. According to the Daily Mail, Rihanna and Rob opted to ride in separate vehicles to avoid drawing attention to themselves. As TMZ noted, this story broke just months after rumors swirled that the pair had been secretly linking up. Sources who spoke to Us Weekly offered even more fun details. "They were sitting closely at the club, whispering in each other's ears and clearly flirting," shared the source. "Rihanna and Rob have been flirting for a while," another source added.

However, Rob never owned up to the dating rumors. When speaking to Ryan Seacrest, Kardashian explained their previous outing. "It's because Rihanna's a friend, and she is friends with my friend Capricorn, and it was Cap's birthday," he said (via E! News). "We all went out to celebrate our friend's birthday. It was fun. It was a good night." A tweet made by Khloe Kardashian one year earlier proves that Rob was not only a friend but also a fan. "Lamar and I are blasting @rihanna in the car and @RobKardashian started singing louder then her music.... Pause... Let her do the singing," she tweeted. Rihanna even responded and complimented the family's reality show.

Rihanna has an interesting history with some of Rob Kardashian's sisters. While her 2011 Twitter interaction with Khloe suggests they were once on friendly terms, it hasn't always been so positive. In 2013, Rihanna seemingly shaded Kendall Jenner. According to Hollywood Life, Jenner tweeted about Rihanna's concert. "If Rihanna doesn't perform Complicated tomorrow I'm gunna be very upset #FavSong!" she said (via Hollywood Life). Unfortunately, Rihanna responded, "Well don't come."

And while this didn't originate from Rihanna's mouth, Kylie Jenner has been accused of imitating Rihanna's signature style on numerous occasions. However, not all the news surrounding Rihanna and the Kardashians has been shady. In March 2022, Kim Kardashian complimented one of Rihanna's fashion-forward maternity looks. "OMGGGGGG, @ Badgalriri best pregnancy style ever," Kim posted to Instagram (via E! News). So they're obviously not feuding right now. Still, given that Rob and Rihanna went on to start families with different partners, they're probably quite happy that they never made things official.