Rihanna is arguably one of the biggest stars on the planet. Since bursting onto the music 15 years ago, the stunning Barbadian singer has become one of the best-selling music artists of all time. She’s won a total of nine Grammy Awards, 13 American Music Awards, and 12 Billboard Music Awards, and has even dipped her toe into the acting pool with roles in movies and TV shows such as Ocean’s 8 and Bates Motel. The 32-year-old icon is also a savvy businesswoman who’s critically praised cosmetics company, Fenty Beauty, is reportedly worth more than $3 billion.
When it comes to Rihanna’s love life—which the “Umbrella” singer keeps very private—fans are always eager to know what’s going on. Who is Rihanna dating? Who are Rihanna’s boyfriends from the past? Here, we take a look at the men the superstar has reportedly been involved with.
Way back in 2007, rumors began to surface that Rihanna was dating Disturbia actor Shia LaBeouf. But LaBeouf debunked this myth two years later when he clarified their relationship in a 2009 Playboy interview, as reported by MTV. While the Transformers star did say they hung out, he admitted: “It never got beyond one date….The spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends.”
Rihanna’s most high-profile romance was with R&B singer Chris Brown. When the pair first got together in 2008, they became one of the hottest celebrity couples in the music industry. However, in 2009, Brown was arrested for physically assaulting the “Diamonds” singer. He pleaded guilty to felony assault and received five years of probation, and was ordered to stay away from his former flame. Photos of Rhianna later surfaced and showed she had sustained multiple injuries as a result of the attack.
Despite the abuse, the pair briefly got back together in 2012, though Rihanna later admitted that their reunion was a mistake. In 2015 she told Vanity Fair:
I was that girl. That girl who felt that as much pain as this relationship is, maybe some people are built stronger than others. Maybe I’m one of those people built to handle shit like this. Maybe I’m the person who’s almost the guardian angel to this person, to be there when they’re not strong enough, when they’re not understanding the world, when they just need someone to encourage them in a positive way and say the right thing.
However, Rihanna soon realized that the relationship was not a healthy one for her. “But you know, you realize after a while that in that situation you’re the enemy. You want the best for them, but if you remind them of their failures, or if you remind them of bad moments in their life, or even if you say I’m willing to put up with something, they think less of you—because they know you don’t deserve what they’re going to give. And if you put up with it, maybe you are agreeing that you [deserve] this, and that’s when I finally had to say, ‘Uh-oh, I was stupid thinking I was built for this.’ Sometimes you just have to walk away.”
The pop star added: “I don’t hate him. I will care about him until the day I die. We’re not friends, but it’s not like we’re enemies. We don’t have much of a relationship now.”
Rihanna started a relationship with pro baseball star Matt Kemp in early 2010. The pair were seen together frequently at games and events and appeared to be having a blast. In the December 2010 issue of Marie Claire UK, the “Work” singer gushed about how happy outfielder made her. “I feel like I smile for real this time,” she said. “The smiles come from inside, and it exudes in everything I do. People feel my energy is different. When I smile they can tell that it’s pure bliss and not just a cover up.”
Rihanna also told Vanity Fair that the paparazzi became a problem early in their relationship.“We were still dating … we were just three months in and I liked his vibe, he was a good guy, and then paparazzi got us on vacation in Mexico. He handled it well; I didn’t. I got so uncomfortable because now what? He’s not even able to be seen with [another] girl, because I’m dragged back into headlines that say he’s cheating on me, and I don’t even [really] know this guy.”
Apparently, Kemp did not like dealing with that kind of madness. By the end of 2010, the couple were no longer together. Us Weekly reported that they called it quits because of Rihanna’s hectic lifestyle and the fact that Kemp couldn’t “keep up with her crazy travel schedule.”
Reportedly, Rihanna briefly dated rapper Travis Scott in 2015. While the relationship was never officially confirmed by either artist, a writer for Complex said that Scott was “holed up with Rihanna” one evening when he was waiting to interview the rapper. The writer also claimed that during the interview, Scott spotted a picture of Rihanna on his phone and started “kissing his right index and middle finger and then touching the low-res image of Rihanna’s face, caressing the screen, and glowing with pride.” Earlier this year, that writer admitted that Scott got angry at the magazine for mentioning details about Rihanna in the article.
Rihanna and Drake have known each other since 2005 and have collaborated on many projects over the years, including the hits “What’s My Name” and “Take Care.” But the pair also appear to have had a longtime on-again, off-again relationship. The duo supposedly hooked up for the first time in 2009, however in a 2010 interview with the New York Times, Drake said it was just a fling. “I was a pawn,” He said. “She was doing exactly what I’ve done to so many women throughout my life, which is show them quality time, then disappear.”
But the singers continued to work and play together, and at the MTV Video Music Awards in 2016, Drake admitted that Rihanna was “someone I’ve been in love with since I was 22 years old.” While Rih-Rih told Vogue in 2018 the pair were no longer friends, rumors of a reunion began swirling earlier this year when the pair were spotted together at a charity event in Brooklyn and exchanged some flirty comments on Instagram.
Hassan Jameel appears to be Rihanna’s most recent ex. The 32-year-old businessman and billionaire reportedly dated the “S&M” singer for three years, from 2017 to 2020. Photos of them together surfaced frequently, and in 2018 Rihanna alluded to her relationship in an interview with Vogue, saying: “I used to feel guilty about taking personal time,” she says, “but I also think I never met someone who was worth it before.”
Sadly, People reported in January that the pair had broken up because “their lives were too different and it was hard to maintain a relationship.”
Who Is Rihanna’s Boyfriend Currently?
So who is Rihanna dating now? People says it’s rapper A$AP Rocky. Rumors of a romance between the two performers began swirling way back in January, with sources confirming that the pair started dating casually soon after Rihanna’s breakup with Jameel. Apparently, the two have been friends for years, and Rihanna is enjoying the time she’s spending with her new man. Most recently, Page Six reported spotting the couple partying together in New York City.